text:
August 27

Pre-1600

 * 410 – The sacking of Rome by the Visigoths ends after three days.
 * 1172 – Henry the Young King and Margaret of France are crowned junior king and queen of England.
 * 1232 – Shikken Hojo Yasutoki of the Kamakura shogunate promulgates the Goseibai Shikimoku, the first Japanese legal code governing the samurai class.
 * 1557 – The Battle of St. Quentin results in Emmanuel Philibert becoming Duke of Savoy.
 * 1593 – Pierre Barrière failed an attempt to assassinate Henry IV of France.
 * 1597 – Jeongyu War: Battle of Chilcheollyang: A Japanese fleet of 500 ships destroys Joseon commander Won Gyun's fleet of 200 ships at Chilcheollyang.
 * 1600 – Ishida Mitsunari's Western Army commences the Siege of Fushimi Castle, which is lightly defended by a much smaller Tokugawa garrison led by Torii Mototada.

1601–1900

 * 1689 – The Treaty of Nerchinsk is signed by Russia and the Qing Empire (Julian calendar).
 * 1776 – American Revolutionary War: Members of the 1st Maryland Regiment repeatedly charged a numerically superior British force during the Battle of Long Island, allowing General Washington and the rest of the American troops to escape.
 * 1791 – French Revolution: Frederick William II of Prussia and Leopold II, Holy Roman Emperor, issue the Declaration of Pillnitz, declaring the joint support of the Holy Roman Empire and Prussia for the French monarchy, agitating the French revolutionaries and contributing to the outbreak of the War of the First Coalition.
 * 1793 – French Revolutionary Wars: The city of Toulon revolts against the French Republic and admits the British and Spanish fleets to seize its port, leading to the Siege of Toulon by French Revolutionary forces.
 * 1798 – Wolfe Tone's United Irish and French forces clash with the British Army in the Battle of Castlebar, part of the Irish Rebellion of 1798, resulting in the creation of the French puppet Republic of Connacht.
 * 1810 – Napoleonic Wars: The French Navy defeats the British Royal Navy, preventing them from taking the harbour of Grand Port on Île de France.
 * 1813 – French Emperor Napoleon I defeats a larger force of Austrians, Russians, and Prussians at the Battle of Dresden.
 * 1828 – Brazil and Argentina recognize the sovereignty of Uruguay in the Treaty of Montevideo
 * 1832 – Black Hawk, leader of the Sauk tribe of Native Americans, surrenders to U.S. authorities, ending the Black Hawk War.
 * 1859 – Petroleum is discovered in Titusville, Pennsylvania, leading to the world's first commercially successful oil well.
 * 1881 – The Georgia hurricane makes landfall near Savannah, Georgia, resulting in an estimated 700 deaths.
 * 1883 – Eruption of Krakatoa: Four enormous explosions almost completely destroy the island of Krakatoa and cause years of climate change.
 * 1893 – The Sea Islands hurricane strikes the United States near Savannah, Georgia, killing between 1,000 and 2,000 people.
 * 1895 – Japanese invasion of Taiwan: Battle of Baguashan: The Empire of Japan decisively defeats a smaller Formosan army at Changhua, crippling the short-lived Republic of Formosa and leading to its surrender two months later.
 * 1896 – Anglo-Zanzibar War: The shortest war in world history (09:02 to 09:40), between the United Kingdom and Zanzibar.

1901–present

 * 1908 – The Qing dynasty promulgates the Qinding Xianfa Dagang, the first constitutional document in the history of China, transforming the Qing empire into a constitutional monarchy.
 * 1914 – World War I: Battle of Étreux: A British rearguard action by the Royal Munster Fusiliers during the Great Retreat.
 * 1914  – World War I: Siege of Tsingtao: A Japanese fleet commanded by Vice Admiral Sadakichi Kato imposes a blockade along the whole coastline of German Tsingtao, initiating the Siege of Tsingtao.
 * 1915 – Attempted assassination of Bishop Patrick Heffron, bishop of the Diocese of Winona, by Rev. Louis M. Lesches.
 * 1916 – World War I: The Kingdom of Romania declares war on Austria-Hungary, entering the war as one of the Allied nations.
 * 1918 – Mexican Revolution: Battle of Ambos Nogales: U.S. Army forces skirmish against Mexican Carrancistas in the only battle of World War I fought on American soil.
 * 1922 – Greco-Turkish War: The Turkish army takes the Aegean city of Afyonkarahisar from the Kingdom of Greece.
 * 1927 – Five Canadian women file a petition to the Supreme Court of Canada, asking: "Does the word 'Persons' in Section 24 of the British North America Act, 1867, include female persons?"
 * 1928 – The Kellogg–Briand Pact outlawing war is signed by fifteen nations. Ultimately sixty-one nations will sign it.
 * 1933 – The first Afrikaans Bible is introduced during a Bible Festival in Bloemfontein.
 * 1939 – First flight of the turbojet-powered Heinkel He 178, the world's first jet aircraft.
 * 1942 – First day of the Sarny Massacre, perpetrated by Germans and Ukrainians.
 * 1943 – World War II: Japanese forces evacuate New Georgia Island in the Pacific Theater of Operations during World War II.
 * 1943  – World War II: Aerial bombardment by the Luftwaffe razes to the ground the village of Vorizia in Crete.
 * 1955 – The first edition of the Guinness Book of Records is published in Great Britain.
 * 1956 – The nuclear power station at Calder Hall in the United Kingdom was connected to the national power grid becoming the world's first commercial nuclear power station to generate electricity on an industrial scale.
 * 1962 – The Mariner 2 unmanned space mission is launched to Venus by NASA.
 * 1963 – An explosion at the Cane Creek potash mine near Moab, Utah kills 18 miners.
 * 1964 – South Vietnamese junta leader Nguyễn Khánh enters into a triumvirate power-sharing arrangement with rival generals Trần Thiện Khiêm and Dương Văn Minh, who had both been involved in plots to unseat Khánh.
 * 1971 – An attempted coup d'état fails in the African nation of Chad. The Government of Chad accuses Egypt of playing a role in the attempt and breaks off diplomatic relations.
 * 1975 – The Governor of Portuguese Timor abandons its capital, Dili, and flees to Atauro Island, leaving control to a rebel group.
 * 1979 – The Troubles: Eighteen British soldiers are killed in an ambush by the Provisional Irish Republican Army near Warrenpoint, Northern Ireland, in the deadliest attack on British forces during Operation Banner. An IRA bomb also kills British royal family member Lord Mountbatten and three others on his boat at Mullaghmore, Republic of Ireland.
 * 1980 – South Korean presidential election: After successfully staging the Coup d'état of May Seventeenth, General Chun Doo-hwan, running unopposed, has the National Conference for Unification elect him President of the Fourth Republic of Korea.
 * 1982 – Turkish military diplomat Colonel Atilla Altıkat is shot and killed in Ottawa. Justice Commandos of the Armenian Genocide claim to be avenging the massacre of $1 1/2$ million Armenians in the 1915 Armenian genocide.
 * 1985 – Major General Muhammadu Buhari, Chairman of the Supreme Military Council of Nigeria, is ousted from power in a coup d'état led by Major General Ibrahim Babangida.
 * 1991 – The European Community recognizes the independence of the Baltic states of Estonia, Latvia and Lithuania.
 * 1991  – Moldova declares independence from the USSR.
 * 1992 – Aeroflot Flight 2808 crashes on approach to Ivanovo Yuzhny Airport, killing all 84 aboard.
 * 2003 – Mars makes its closest approach to Earth in nearly 60,000 years, passing 34646418 mi distant.
 * 2003  – The first six-party talks, involving South and North Korea, the United States, China, Japan and Russia, convene to find a peaceful resolution to the security concerns of the North Korean nuclear weapons program.
 * 2006 – Comair Flight 5191 crashes on takeoff from Blue Grass Airport in Lexington, Kentucky, bound for Hartsfield–Jackson Atlanta International Airport in Atlanta. Of the passengers and crew, 49 of 50 are confirmed dead in the hours following the crash.
 * 2009 – Internal conflict in Myanmar: The Burmese military junta and ethnic armies begin three days of violent clashes in the Kokang Special Region.
 * 2011 – Hurricane Irene strikes the United States east coast, killing 47 and causing an estimated $15.6 billion in damage.

Pre-1600

 * 865 – Rhazes, Persian polymath (d. 925)
 * 1407 – Ashikaga Yoshikazu, Japanese shōgun (d. 1425)
 * 1471 – George, Duke of Saxony (d. 1539)
 * 1487 – Anna of Brandenburg (d. 1514)
 * 1512 – Friedrich Staphylus, German theologian (d. 1564)
 * 1542 – John Frederick, Duke of Pomerania and Protestant Bishop of Cammin (d. 1600)
 * 1545 – Alexander Farnese, Duke of Parma (d. 1592)

1601–1900

 * 1624 – Koxinga, Chinese-Japanese Ming loyalist (d. 1662)
 * 1637 – Charles Calvert, 3rd Baron Baltimore, English politician, 2nd Proprietor of Maryland (d. 1715)
 * 1665 – John Hervey, 1st Earl of Bristol, English politician (d. 1751)
 * 1669 – Anne Marie d'Orléans, queen of Sardinia (d. 1728)
 * 1677 – Otto Ferdinand von Abensberg und Traun, Austrian general (d. 1748)
 * 1724 – John Joachim Zubly, Swiss-American pastor, planter, and politician (d. 1781)
 * 1730 – Johann Georg Hamann, German philosopher and author (d. 1788)
 * 1770 – Georg Wilhelm Friedrich Hegel, German philosopher and academic (d. 1831)
 * 1785 – Agustín Gamarra, Peruvian general and politician, 10th and 14th President of Peru (d. 1841)
 * 1795 – Giorgio Mitrovich, Maltese politician (d. 1885)
 * 1803 – Edward Beecher, American minister and theologian (d. 1895)
 * 1809 – Hannibal Hamlin, American publisher and politician, 15th Vice President of the United States (d. 1891)
 * 1812 – Bertalan Szemere, Hungarian poet and politician, 3rd Prime Minister of Hungary (d. 1869)
 * 1822 – William Hayden English, American politician, U.S. Representative from Indiana and Democratic Vice-Presidential nominee (d. 1896)
 * 1827 – Charles Lilley, English-Australian politician, 4th Premier of Queensland (d. 1897)
 * 1845 – Ödön Lechner, Hungarian architect, designed the Museum of Applied Arts and the Church of St Elisabeth (d. 1914)
 * 1845  – Friedrich Martens, Estonian-Russian historian, lawyer, and diplomat (d. 1909)
 * 1856 – Ivan Franko, Ukrainian author and poet (d. 1916)
 * 1858 – Giuseppe Peano, Italian mathematician and philosopher (d. 1932)
 * 1864 – Hermann Weingärtner, German gymnast (d. 1919)
 * 1865 – James Henry Breasted, American archaeologist and historian (d. 1935)
 * 1865  – Charles G. Dawes, American general and politician, 30th Vice President of the United States, Nobel Prize laureate (d. 1951)
 * 1868 – Hong Beom-do, Korean general and activist (d. 1943)
 * 1870 – Amado Nervo, Mexican journalist, poet, and diplomat (d. 1919)
 * 1871 – Theodore Dreiser, American novelist and journalist (d. 1945)
 * 1874 – Carl Bosch, German chemist and engineer, Nobel Prize laureate (d. 1940)
 * 1875 – Katharine McCormick, American biologist, philanthropist, and activist (d. 1967)
 * 1877 – Charles Rolls, English engineer and businessman, co-founded Rolls-Royce Limited (d. 1910)
 * 1877  – Ernst Wetter, Swiss lawyer and politician, 48th President of the Swiss Confederation (d. 1963)
 * 1878 – Pyotr Nikolayevich Wrangel, Russian general (d. 1928)
 * 1884 – Vincent Auriol, French lawyer and politician, President of the French Republic (d. 1966)
 * 1884  – Denis G. Lillie, British biologist, member of the 1910–1913 Terra Nova Expedition (d. 1963)
 * 1886 – Rebecca Clarke, English viola player and composer (d. 1979)
 * 1890 – Man Ray, American-French photographer and painter (d. 1976)
 * 1895 – Andreas Alföldi, Hungarian archaeologist and historian (d. 1981)
 * 1896 – Kenji Miyazawa, Japanese author and poet (d. 1933)
 * 1898 – Gaspard Fauteux, Canadian businessman and politician, 19th Lieutenant Governor of Quebec (d. 1963)
 * 1899 – C. S. Forester, English novelist (d. 1966)

1901–present

 * 1904 – Alar Kotli, Estonian architect (d. 1963)
 * 1904  – Norah Lofts, English author (d. 1983)
 * 1904  – John Hay Whitney, American businessman, publisher, and diplomat, founded J.H. Whitney & Company (d. 1982)
 * 1905 – Aris Velouchiotis, Greek soldier (d. 1945)
 * 1906 – Ed Gein, American murderer and body snatcher, The Butcher of Plainfield (d. 1982)
 * 1908 – Don Bradman, Australian cricketer and manager (d. 2001)
 * 1908  – Lyndon B. Johnson, American commander and politician, 36th President of the United States (d. 1973)
 * 1909 – Sylvère Maes, Belgian cyclist (d. 1966)
 * 1909  – Charles Pozzi, French race car driver (d. 2001)
 * 1909  – Lester Young, American saxophonist and clarinet player (d. 1959)
 * 1911 – Kay Walsh, English actress and dancer (d. 2005)
 * 1912 – Gloria Guinness, Mexican journalist (d. 1980)
 * 1915 – Norman Foster Ramsey Jr., American physicist and academic, Nobel Prize laureate (d. 2011)
 * 1916 – Gordon Bashford, English engineer, co-designed the Range Rover (d. 1991)
 * 1916  – Tony Harris, South African cricketer and rugby player (d. 1993)
 * 1916  – Martha Raye, American actress and comedian (d. 1994)
 * 1917 – Peanuts Lowrey, American baseball player, coach, and manager (d. 1986)
 * 1918 – Jelle Zijlstra, Dutch economist and politician, Prime Minister of the Netherlands (d. 2001)
 * 1919 – Pee Wee Butts, American baseball player and coach (d. 1972)
 * 1919  – Murray Grand, American singer-songwriter and pianist (d. 2007)
 * 1920 – Baptiste Manzini, American football player (d. 2008)
 * 1920  – James Molyneaux, Baron Molyneaux of Killead, Northern Irish soldier and politician (d. 2015)
 * 1921 – Georg Alexander, Duke of Mecklenburg (d. 1996)
 * 1921  – Leo Penn, American actor, director, and screenwriter (d. 1998)
 * 1922 – Roelof Kruisinga, Dutch physician and politician, Minister of Defence for The Netherlands (d. 2012)
 * 1923 – Jimmy Greenhalgh, English footballer and manager (d. 2013)
 * 1924 – David Rowbotham, Australian journalist and poet (d. 2010)
 * 1924  – Rosalie E. Wahl, American lawyer and jurist (d. 2013)
 * 1925 – Andrea Cordero Lanza di Montezemolo, Italian cardinal (d. 2017)
 * 1925  – Nat Lofthouse, English footballer and manager (d. 2011)
 * 1925  – Saiichi Maruya, Japanese author and critic (d. 2012)
 * 1925  – Bill Neilson, Australian politician, 34th Premier of Tasmania (d. 1989)
 * 1925  – Jaswant Singh Neki, Indian poet and academic (d. 2015)
 * 1925  – Carter Stanley, American bluegrass singer-songwriter and guitarist (d. 1966)
 * 1926 – George Brecht, American-German chemist and composer (d. 2008)
 * 1926  – Kristen Nygaard, Norwegian computer scientist and academic (d. 2002)
 * 1928 – Péter Boross, Hungarian lawyer and politician, 54th Prime Minister of Hungary
 * 1928  – Mangosuthu Buthelezi, South African politician, Chief Minister of KwaZulu (d. 2023)
 * 1928  – Joan Kroc, American philanthropist (d. 2003)
 * 1929 – Ira Levin, American novelist, playwright, and songwriter (d. 2007)
 * 1929  – George Scott, Canadian-American wrestler and promoter (d. 2014)
 * 1930 – Aase Foss Abrahamsen, Norwegian writer (d. 2023)
 * 1930  – Gholamreza Takhti, Iranian wrestler and politician (d. 1968)
 * 1931 – Sri Chinmoy, Indian-American guru and poet (d. 2007)
 * 1931  – Joe Cunningham, American baseball player and coach (d. 2021)
 * 1932 – Cor Brom, Dutch footballer and manager (d. 2008)
 * 1932  – Antonia Fraser, English historian and author
 * 1935 – Ernie Broglio, American baseball player (d. 2019)
 * 1935  – Michael Holroyd, English author
 * 1935  – Frank Yablans, American screenwriter and producer (d. 2014)
 * 1936 – Joel Kovel, American scholar and author (d. 2018)
 * 1936  – Lien Chan, Taiwanese politician,  Vice President of the Republic of China
 * 1937 – Alice Coltrane, American pianist and composer (d. 2007)
 * 1937  – Tommy Sands, American pop singer and actor
 * 1939 – William Least Heat-Moon, American travel writer and historian
 * 1939  – Edward Patten, American singer-songwriter and producer (d. 2005)
 * 1939 – Nikola Pilić, Yugoslav tennis player and coach
 * 1940 – Fernest Arceneaux, American singer and accordion player (d. 2008)
 * 1940  – Sonny Sharrock, American guitarist (d. 1994)
 * 1941 – Cesária Évora, Cape Verdean singer (d. 2011)
 * 1941  – János Konrád, Hungarian water polo player and swimmer (d. 2014)
 * 1941  – Harrison Page, American actor
 * 1942 – Daryl Dragon, American keyboard player and songwriter (d. 2019)
 * 1942  – Brian Peckford, Canadian educator and politician, 3rd Premier of Newfoundland and Labrador
 * 1943 – Chuck Girard, American singer-songwriter and pianist
 * 1943  – Bob Kerrey, American lieutenant and politician, Medal of Honor recipient, 35th Governor of Nebraska
 * 1943  – Tuesday Weld, American model and actress
 * 1944 – G. W. Bailey, American actor
 * 1944  – Tim Bogert, American singer and bass player (d. 2021)
 * 1945 – Douglas R. Campbell, Canadian lawyer and judge
 * 1945  – Marianne Sägebrecht, German actress
 * 1946 – Tony Howard, Barbadian cricketer and manager
 * 1947 – Barbara Bach, American actress and model
 * 1947  – Halil Berktay, Turkish historian and academic
 * 1947  – Kirk Francis, American engineer and producer
 * 1947  – Peter Krieg, German director, producer, and screenwriter (d. 2009)
 * 1947  – John Morrison, New Zealand cricketer and politician
 * 1947  – Gavin Pfuhl, South African cricketer and sportscaster (d. 2002)
 * 1948 – John Mehler, American drummer
 * 1948  – Sgt. Slaughter, American wrestler
 * 1948  – Deborah Swallow, English historian and curator
 * 1948  – Philippe Vallois, French director and screenwriter
 * 1949 – Jeff Cook, American singer-songwriter and guitarist (d. 2022)
 * 1949  – Leah Jamieson, American computer scientist, engineer, and academic
 * 1949  – Ann Murray, Irish soprano
 * 1950 – Charles Fleischer, American comedian and actor
 * 1950  – Neil Murray, Scottish bass player and songwriter
 * 1950  – Edmund Weiner, English lexicographer and author
 * 1951 – Buddy Bell, American baseball player and manager
 * 1951  – Mack Brown, American football player and coach
 * 1951  – Randall Garrison, American-Canadian criminologist and politician
 * 1952 – Paul Reubens, American actor and comedian (d. 2023)
 * 1953 – Tom Berryhill, American businessman and politician (d. 2020)
 * 1953  – Alex Lifeson, Canadian singer-songwriter, guitarist, and producer
 * 1953  – Joan Smith, English journalist and author
 * 1953  – Peter Stormare, Swedish actor, director, and playwright
 * 1954 – John Lloyd, English tennis player and sportscaster
 * 1954  – Rajesh Thakker, English physician and academic
 * 1954  – Derek Warwick, English race car driver
 * 1955 – Robert Richardson, American cinematographer
 * 1955  – Diana Scarwid, American actress
 * 1956 – Glen Matlock, English singer-songwriter and bass player
 * 1957 – Jeff Grubb, American game designer and author
 * 1957  – Bernhard Langer, German golfer
 * 1958 – Sergei Krikalev, Russian engineer and astronaut
 * 1958  – Tom Lanoye, Belgian author, poet, and playwright
 * 1958  – Hugh Orde, British police officer
 * 1959 – Daniela Romo, Mexican singer, actress and TV hostess
 * 1959  – Gerhard Berger, Austrian race car driver
 * 1959  – Juan Fernando Cobo, Colombian painter and sculptor
 * 1959  – Denice Denton, American engineer and academic (d. 2006)
 * 1959  – Frode Fjellheim, Norwegian pianist and composer
 * 1959  – András Petőcz, Hungarian author and poet
 * 1959  – Jeanette Winterson, English journalist and novelist
 * 1961 – Yolanda Adams, American singer, producer, and actress
 * 1961  – Mark Curry, English television host and actor
 * 1961  – Tom Ford, American fashion designer and film director
 * 1961  – Steve McDowall, New Zealand rugby player
 * 1961  – Helmut Winklhofer, German footballer
 * 1962 – Adam Oates, Canadian ice hockey player
 * 1964 – Stephan Elliott, Australian actor, director, and screenwriter
 * 1964  – Paul Bernardo, Canadian serial rapist and murderer
 * 1965 – Scott Dibble, American lawyer and politician
 * 1965  – Wayne James, Zimbabwean cricketer and coach
 * 1965  – Ange Postecoglou, Greek-Australian footballer and coach
 * 1966 – Jeroen Duyster, Dutch rower
 * 1966  – René Higuita, Colombian footballer
 * 1966  – Juhan Parts, Estonian lawyer and politician, 14th Prime Minister of Estonia
 * 1967 – Ogie Alcasid, Filipino singer-songwriter, producer, and actor
 * 1967  – Rob Burnett, American football player and sportscaster
 * 1968 – Eric "Bobo" Correa, American musician
 * 1968  – Daphne Koller, Israeli-American computer scientist and academic
 * 1968  – Michael Long, New Zealand golfer
 * 1968  – Matthew Ridge, New Zealand rugby player and sportscaster
 * 1969 – Mark Ealham, English cricketer
 * 1969  – Cesar Millan, Mexican-American dog trainer, television personality, and author
 * 1969  – Reece Shearsmith, English actor, comedian and writer
 * 1969  – Chandra Wilson, American actress and director
 * 1970 – Andy Bichel, Australian cricketer and coach
 * 1970  – Mark Ilott, English cricketer
 * 1970  – Pokwang,  Filipino comedian, actress, television host and singer
 * 1970  – Tony Kanal, British-American bass player. songwriter, and record producer
 * 1970  – Jim Thome, American baseball player and manager
 * 1970  – Karl Unterkircher, Italian mountaineer (d. 2008)
 * 1971 – Ernest Faber, Dutch footballer and manager
 * 1971  – Kyung Lah, South Korean-American journalist
 * 1971  – Hisayuki Okawa, Japanese runner
 * 1971  – Aygül Özkan, German lawyer and politician
 * 1972 – Jaap-Derk Buma, Dutch field hockey player
 * 1972  – Denise Lewis, English heptathlete
 * 1972  – Jimmy Pop, American singer-songwriter and guitarist
 * 1972  – The Great Khali, Indian professional wrestler
 * 1973 – Danny Coyne, Welsh footballer
 * 1973  – Dietmar Hamann, German footballer and manager
 * 1973  – Burak Kut, Turkish singer-songwriter
 * 1973  – Johan Norberg, Swedish historian and author
 * 1974 – Aaron Downey, Canadian ice hockey player and coach
 * 1974  – Manny Fernandez, Canadian ice hockey player
 * 1974  – Michael Mason, New Zealand cricketer
 * 1974  – José Vidro, Puerto Rican-American baseball player
 * 1974  – Mohammad Yousuf, Pakistani cricketer
 * 1975 – Blake Adams, American golfer
 * 1975  – Mase, American rapper, songwriter and pastor
 * 1975  – Jonny Moseley, Puerto Rican-American skier and television host
 * 1975  – Marko Rudan, Australian footballer and manager
 * 1976 – Sarah Chalke, Canadian actress
 * 1976  – Audrey C. Delsanti, French astronomer and biologist
 * 1976  – Milano Collection A.T., Japanese wrestler
 * 1976  – Carlos Moyá, Spanish-Swiss tennis player
 * 1976  – Mark Webber, Australian race car driver
 * 1977 – Deco, Brazilian-Portuguese footballer
 * 1977  – Justin Miller, American baseball player (d. 2013)
 * 1978 – Demetria McKinney, American actress and singer
 * 1979 – Sarah Neufeld, Canadian violinist
 * 1979  – Aaron Paul, American actor and producer
 * 1979  – Karel Rachůnek, Czech ice hockey player (d. 2011)
 * 1979  – Rusty Smith, American speed skater
 * 1981 – Patrick J. Adams, Canadian actor
 * 1981  – Maxwell Cabelino Andrade, Brazilian footballer
 * 1981  – Chantal Djotodia, Beninese-Central African nurse and politician
 * 1981  – Alessandro Gamberini, Italian footballer
 * 1981  – Karla Mosley, American actress
 * 1983 – Joanna McGilchrist, English rugby player and physiotherapist
 * 1984 – David Bentley, English footballer
 * 1984  – Amanda Fuller, American actress
 * 1984  – Sulley Muntari, Ghanaian footballer
 * 1985 – Kayla Ewell, American actress
 * 1985  – Kevan Hurst, English footballer
 * 1985  – Nikica Jelavić, Croatian footballer
 * 1985  – Alexandra Nechita, Romanian-American painter and sculptor
 * 1986 – Lana Bastašić, Serbian-Bosnian author and translator
 * 1986  – Sebastian Kurz, Austrian politician, 25th Chancellor of Austria
 * 1986  – Mario, American singer and actor
 * 1987 – Joel Grant, English-Jamaican footballer
 * 1987  – Darren McFadden, American football player
 * 1988 – Alexa PenaVega, American actress and singer
 * 1989 – Romain Amalfitano, French footballer
 * 1989  – Juliana Cannarozzo, American figure skater and actress
 * 1990 – Tori Bowie, American athlete (d. 2023)
 * 1990  – Luuk de Jong, Dutch footballer
 * 1991 – Lee Sung-yeol, South Korean actor and singer
 * 1992 – Blake Jenner, American actor and singer
 * 1992  – Stephen Morris, American football player
 * 1992  – Kim Petras, German singer-songwriter
 * 1992  – Ayame Goriki, Japanese actress and singer
 * 1993 – Sarah Hecken, German figure skater
 * 1993  – Olivier Le Gac, French cyclist
 * 1994 – Ellar Coltrane, American actor
 * 1994  – Breanna Stewart, American basketball player
 * 1995 – Jessie Mei Li, English actress
 * 1995  – Sergey Sirotkin, Russian race car driver
 * 1998 – Kevin Huerter, American basketball player
 * 1998  – Rod Wave, American rapper, singer, and songwriter
 * 2001 – Franz Wagner, German basketball player

Pre-1600

 * 542 – Caesarius of Arles, French bishop and saint (b. 470)
 * 749 – Qahtaba ibn Shabib al-Ta'i, Persian general
 * 827 – Pope Eugene II
 * 923 – Ageltrude, queen of Italy and Holy Roman Empress
 * 1146 – King Eric III of Denmark
 * 1255 – Little Saint Hugh of Lincoln (b. 1247)
 * 1312 – Arthur II, Duke of Brittany (b. 1261)
 * 1394 – Emperor Chōkei of Japan (b. 1343)
 * 1450 – Reginald West, 6th Baron De La Warr, English politician (b. 1395)
 * 1521 – Josquin des Prez, Flemish composer (b. 1450)
 * 1545 – Piotr Gamrat, Polish archbishop (b. 1487)
 * 1576 – Titian, Italian painter and educator (b. 1488)
 * 1590 – Pope Sixtus V (b. 1521)

1601–1900

 * 1611 – Tomás Luis de Victoria, Spanish composer (b. c. 1548)
 * 1635 – Lope de Vega, Spanish poet and playwright (b. 1562)
 * 1664 – Francisco de Zurbarán, Spanish painter and educator (b. 1598)
 * 1748 – James Thomson, Scottish poet and playwright (b. 1700)
 * 1782 – John Laurens, American Revolutionary and abolitionist (b. 1754)
 * 1828 – Eise Eisinga, Dutch astronomer and academic, built the Eisinga Planetarium (b. 1744)
 * 1857 – Rufus Wilmot Griswold, American anthologist, poet, and critic (b. 1815)
 * 1865 – Thomas Chandler Haliburton, Canadian judge and politician (b. 1796)
 * 1871 – William Whiting Boardman, American lawyer and politician (b. 1794)
 * 1875 – William Chapman Ralston, American businessman and financier, founded the Bank of California (b. 1826)
 * 1891 – Samuel C. Pomeroy, American businessman and politician (b. 1816)

1901–present

 * 1903 – Kusumoto Ine, first Japanese female doctor of Western medicine (b. 1827)
 * 1909 – Emil Christian Hansen, Danish physiologist and mycologist (b. 1842)
 * 1922 – Reşat Çiğiltepe, Turkish colonel (b. 1879)
 * 1929 – Herman Potočnik, Croatian-Austrian engineer (b. 1892)
 * 1931 – Frank Harris, Irish-American journalist and author (b. 1856)
 * 1931  – Willem Hubert Nolens, Dutch priest and politician (b. 1860)
 * 1931  – Francis Marion Smith, American miner and businessman (b. 1846)
 * 1935 – Childe Hassam, American painter and academic (b. 1859)
 * 1944 – Georg von Boeselager, German soldier (b. 1915)
 * 1945 – Hubert Pál Álgyay, Hungarian engineer, designed the Petőfi Bridge (b. 1894)
 * 1948 – Charles Evans Hughes, American lawyer and politician, 11th Chief Justice of the United States (b. 1862)
 * 1950 – Cesare Pavese, Italian author, poet, and critic (b. 1908)
 * 1956 – Pelageya Shajn, Russian astronomer and academic (b. 1894)
 * 1958 – Ernest Lawrence, American physicist and academic, Nobel Prize laureate (b. 1901)
 * 1963 – W. E. B. Du Bois, American sociologist, historian, and activist (b. 1868)
 * 1963  – Inayatullah Khan Mashriqi, Pakistani mathematician and scholar (b. 1888)
 * 1964 – Gracie Allen, American actress and comedian (b. 1895)
 * 1965 – Le Corbusier, Swiss-French architect and urban planner, designed the Philips Pavilion (b. 1887)
 * 1967 – Brian Epstein, English businessman and manager (b. 1934)
 * 1968 – Princess Marina of Greece and Denmark (b. 1906)
 * 1969 – Ivy Compton-Burnett, English author (b. 1884)
 * 1969  – Erika Mann, German actress and author (b. 1905)
 * 1971 – Bennett Cerf, American publisher, co-founded Random House (b. 1898)
 * 1971  – Margaret Bourke-White, American photographer and journalist  (b. 1906)
 * 1975 – Haile Selassie, Ethiopian emperor (b. 1892)
 * 1978 – Gordon Matta-Clark, American painter and illustrator (b. 1943)
 * 1978  – Ieva Simonaitytė, Lithuanian author and poet (b. 1897)
 * 1979 – Louis Mountbatten, 1st Earl Mountbatten of Burma, English admiral and politician, 44th Governor-General of India (b. 1900)
 * 1980 – Douglas Kenney, American actor, producer, and screenwriter (b. 1947)
 * 1981 – Valeri Kharlamov, Russian ice hockey player (b. 1948)
 * 1990 – Avdy Andresson, Estonian soldier and diplomat (b. 1899)
 * 1990  – Stevie Ray Vaughan, American singer-songwriter, guitarist, and producer (b. 1954)
 * 1992 – Bengt Holbek, Danish folklorist (b. 1933)
 * 1994 – Frank Jeske, German footballer (b. 1960)
 * 1996 – Greg Morris, American actor (b. 1933)
 * 1998 – Essie Summers, New Zealand author (b. 1912)
 * 1999 – Hélder Câmara, Brazilian archbishop and theologian (b. 1909)
 * 2001 – Michael Dertouzos, Greek-American computer scientist and academic (b. 1936)
 * 2001  – Abu Ali Mustafa, Palestinian politician (b. 1938)
 * 2002 – Edwin Louis Cole, American religious leader and author (b. 1922)
 * 2003 – Pierre Poujade, French soldier and politician (b. 1920)
 * 2004 – Willie Crawford, American baseball player (b. 1946)
 * 2005 – Giorgos Mouzakis, Greek trumpet player and composer (b. 1922)
 * 2005  – Seán Purcell, Irish footballer (b. 1929)
 * 2006 – Hrishikesh Mukherjee, Indian director, producer, and screenwriter (b. 1922)
 * 2006  – Jesse Pintado, Mexican-American guitarist (b. 1969)
 * 2007 – Emma Penella, Spanish actress (b. 1930)
 * 2009 – Sergey Mikhalkov, Russian author and poet (b. 1913)
 * 2010 – Anton Geesink, Dutch martial artist (b. 1934)
 * 2010  – Luna Vachon, Canadian-American wrestler and manager (b. 1962)
 * 2012 – Neville Alexander, South African linguist and activist (b. 1936)
 * 2012  – Malcolm Browne, American journalist and photographer (b. 1931)
 * 2012  – Art Heyman, American basketball player (b. 1941)
 * 2012  – Ivica Horvat, Croatian footballer and manager (b. 1926)
 * 2012  – Richard Kingsland, Australian captain and pilot (b. 1916)
 * 2012  – Geliy Korzhev, Russian painter (b. 1925)
 * 2013 – Chen Liting, Chinese director and playwright (b. 1910)
 * 2013  – Bill Peach, Australian journalist (b. 1935)
 * 2013  – Dave Thomas, Welsh golfer and architect (b. 1934)
 * 2014 – Jacques Friedel, French physicist and academic (b. 1921)
 * 2014  – Valeri Petrov, Bulgarian poet, playwright, and screenwriter (b. 1920)
 * 2014  – Benno Pludra, German author (b. 1925)
 * 2015 – Kazi Zafar Ahmed, Bangladeshi politician, 8th Prime Minister of Bangladesh (b. 1939)
 * 2015  – Pascal Chaumeil, French director and screenwriter (b. 1961)
 * 2015  – Darryl Dawkins, American basketball player and coach (b. 1957)
 * 2016 – Cookie, Australian Major Mitchell's cockatoo, oldest recorded parrot (b. 1933)

Holidays and observances

 * Christian feast day:
 * Baculus of Sorrento
 * Caesarius of Arles
 * Decuman
 * Gebhard of Constance
 * Euthalia
 * John of Pavia
 * Lycerius (or: Glycerius, Lizier)
 * Máel Ruba (or Rufus) (Scotland)
 * Margaret the Barefooted
 * Monica of Hippo, mother of Augustine of Hippo
 * Narnus
 * Our Lady of La Vang
 * Phanourios of Rhodes
 * Rufus and Carpophorus
 * Syagrius of Autun
 * Thomas Gallaudet and Henry Winter Syle (Episcopal Church)
 * August 27 (Eastern Orthodox liturgics)
 * Independence Day (Republic of Moldova), celebrates the independence of Moldova from the USSR in 1991.
 * Lyndon Baines Johnson Day (Texas, United States)

title: August 27


text:
Alcohol (chemistry)

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl (\sOH) functional group bound to carbon. Alcohols range from the simple, like methanol and ethanol, to complex, like sugars and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

History
The flammable nature of the exhalations of wine was already known to ancient natural philosophers such as Aristotle (384–322 BCE), Theophrastus (c. 371–287 BCE), and Pliny the Elder (23/24–79 CE). However, this did not immediately lead to the isolation of alcohol, even despite the development of more advanced distillation techniques in second- and third-century Roman Egypt. An important recognition, first found in one of the writings attributed to Jābir ibn Ḥayyān (ninth century CE), was that by adding salt to boiling wine, which increases the wine's relative volatility, the flammability of the resulting vapors may be enhanced. The distillation of wine is attested in Arabic works attributed to al-Kindī (c. 801–873 CE) and to al-Fārābī (c. 872–950), and in the 28th book of al-Zahrāwī's (Latin: Abulcasis, 936–1013) Kitāb al-Taṣrīf (later translated into Latin as Liber servatoris). In the twelfth century, recipes for the production of aqua ardens ("burning water", i.e., alcohol) by distilling wine with salt started to appear in a number of Latin works, and by the end of the thirteenth century, it had become a widely known substance among Western European chemists.

The works of Taddeo Alderotti (1223–1296) describe a method for concentrating alcohol involving repeated fractional distillation through a water-cooled still, by which an alcohol purity of 90% could be obtained. The medicinal properties of ethanol were studied by Arnald of Villanova (1240–1311 CE) and John of Rupescissa (c. 1310–1366), the latter of whom regarded it as a life-preserving substance able to prevent all diseases (the aqua vitae or "water of life", also called by John the quintessence of wine).

Etymology
The word "alcohol" derives from the Arabic kohl (الكحل), a powder used as an eyeliner. The first part of the word (al-) is the Arabic definite article, equivalent to the in English. The second part of the word (kuḥl) has several antecedents in Semitic languages, ultimately deriving from the Akkadian (guḫlum), meaning stibnite or antimony.

Like its antecedents in Arabic and older languages, the term alcohol was originally used for the very fine powder produced by the sublimation of the natural mineral stibnite to form antimony trisulfide Sb2S3. It was considered to be the essence or "spirit" of this mineral. It was used as an antiseptic, eyeliner, and cosmetic. Later the meaning of alcohol was extended to distilled substances in general, and then narrowed again to ethanol, when "spirits" was a synonym for hard liquor.

Paracelsus and Libavius both used the term alcohol to denote a fine powder, the latter speaking of an alcohol derived from antimony. At the same time Paracelsus uses the word for a volatile liquid; alcool or alcool vini occurs often in his writings.

Bartholomew Traheron, in his 1543 translation of John of Vigo, introduces the word as a term used by "barbarous" authors for "fine powder." Vigo wrote: "the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre."

The 1657 Lexicon Chymicum, by William Johnson glosses the word as "antimonium sive stibium." By extension, the word came to refer to any fluid obtained by distillation, including "alcohol of wine," the distilled essence of wine. Libavius in Alchymia (1594) refers to "vini alcohol vel vinum alcalisatum". Johnson (1657) glosses alcohol vini as "quando omnis superfluitas vini a vino separatur, ita ut accensum ardeat donec totum consumatur, nihilque fæcum aut phlegmatis in fundo remaneat." The word's meaning became restricted to "spirit of wine" (the chemical known today as ethanol) in the 18th century and was extended to the class of substances so-called as "alcohols" in modern chemistry after 1850.

The term ethanol was invented in 1892, blending "ethane" with the "-ol" ending of "alcohol", which was generalized as a libfix.

The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks.

The suffix -ol appears in the International Union of Pure and Applied Chemistry (IUPAC) chemical name of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix hydroxy- is used in its IUPAC name. The suffix -ol in non-IUPAC names (such as paracetamol or cholesterol) also typically indicates that the substance is an alcohol. However, some compounds that contain hydroxyl functional groups have trivial names that do not include the suffix -ol or the prefix hydroxy-, e.g. the sugars glucose and sucrose.

Systematic names
IUPAC nomenclature is used in scientific publications, and in writings where precise identification of the substance is important. In naming simple alcohols, the name of the alkane chain loses the terminal e and adds the suffix -ol, e.g., as in "ethanol" from the alkane chain name "ethane". When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the -ol: propan-1-ol for CH3CH2CH2OH, propan-2-ol for CH3CH(OH)CH3. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then the prefix hydroxy-is used, e.g., as in 1-hydroxy-2-propanone (CH3C(O)CH2OH). Compounds having more than one hydroxy group are called polyols. They are named using suffixes -diol, -triol, etc., following a list of the position numbers of the hydroxyl groups, as in propane-1,2-diol for CH3CH(OH)CH2OH (propylene glycol).

In cases where the hydroxy group is bonded to an sp2 carbon on an aromatic ring, the molecule is classified separately as a phenol and is named using the IUPAC rules for naming phenols. Phenols have distinct properties and are not classified as alcohols.

Common names
In other less formal contexts, an alcohol is often called with the name of the corresponding alkyl group followed by the word "alcohol", e.g., methyl alcohol, ethyl alcohol. Propyl alcohol may be n-propyl alcohol or isopropyl alcohol, depending on whether the hydroxyl group is bonded to the end or middle carbon on the straight propane chain. As described under systematic naming, if another group on the molecule takes priority, the alcohol moiety is often indicated using the "hydroxy-" prefix.

In archaic nomenclature, alcohols can be named as derivatives of methanol using "-carbinol" as the ending. For instance, (CH3)3COH can be named trimethylcarbinol.

Primary, secondary, and tertiary
Alcohols are then classified into primary, secondary (sec-, s-), and tertiary (tert-, t-), based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl functional group. The respective numeric shorthands 1°, 2°, and 3° are sometimes used in informal settings. The primary alcohols have general formulas RCH2OH. The simplest primary alcohol is methanol (CH3OH), for which R = H, and the next is ethanol, for which R = CH3, the methyl group. Secondary alcohols are those of the form RR'CHOH, the simplest of which is 2-propanol (R = R' = CH3). For the tertiary alcohols, the general form is RR'R"COH. The simplest example is tert-butanol (2-methylpropan-2-ol), for which each of R, R', and R" is CH3. In these shorthands, R, R', and R" represent substituents, alkyl or other attached, generally organic groups.

Applications

Alcohols have a long history of myriad uses. For simple mono-alcohols, which is the focus on this article, the following are most important industrial alcohols: Methanol is the most common industrial alcohol, with about 12 million tons/y produced in 1980. The combined capacity of the other alcohols is about the same, distributed roughly equally.
 * methanol, mainly for the production of formaldehyde and as a fuel additive
 * ethanol, mainly for alcoholic beverages, fuel additive, solvent
 * 1-propanol, 1-butanol, and isobutyl alcohol for use as a solvent and precursor to solvents
 * C6–C11 alcohols used for plasticizers, e.g. in polyvinylchloride
 * fatty alcohol (C12–C18), precursors to detergents

Toxicity
With respect to acute toxicity, simple alcohols have low acute toxicities. Doses of several milliliters are tolerated. For pentanols, hexanols, octanols, and longer alcohols, LD50 range from 2–5 g/kg (rats, oral). Ethanol is less acutely toxic. All alcohols are mild skin irritants.

Methanol and ethylene glycol are more toxic than other simple alcohols. Their metabolism is affected by the presence of ethanol, which has a higher affinity for liver alcohol dehydrogenase. In this way, methanol will be excreted intact in urine.

Physical properties
In general, the hydroxyl group makes alcohols polar. Those groups can form hydrogen bonds to one another and to most other compounds. Owing to the presence of the polar OH alcohols are more water-soluble than simple hydrocarbons. Methanol, ethanol, and propanol are miscible in water. 1-Butanol, with a four-carbon chain, is moderately soluble.

Because of hydrogen bonding, alcohols tend to have higher boiling points than comparable hydrocarbons and ethers. The boiling point of the alcohol ethanol is 78.29 °C, compared to 69 °C for the hydrocarbon hexane, and 34.6 °C for diethyl ether.

Occurrence in nature
Alcohols occur widely in nature, as derivatives of glucose such as cellulose and hemicellulose, and in phenols and their derivatives such as lignin. Starting from biomass, 180 billion tons/y of complex carbohydrates (sugar polymers) are produced commercially (as of 2014). Many other alcohols are pervasive in organisms, as manifested in other sugars such as fructose and sucrose, in polyols such as glycerol, and in some amino acids such as serine. Simple alcohols like methanol, ethanol, and propanol occur in modest quantities in nature, and are industrially synthesized in large quantities for use as chemical precursors, fuels, and solvents.

Hydroxylation
Many alcohols are produced by hydroxylation, i.e., the installation of a hydroxy group using oxygen or a related oxidant. Hydroxylation is the means by which the body processes many poisons, converting lipophilic compounds into hydrophilic derivatives that are more readily excreted. Enzymes called hydroxylases and oxidases facilitate these conversions.

Many industrial alcohols, such as cyclohexanol for the production of nylon, are produced by hydroxylation.

Ziegler and oxo processes
In the Ziegler process, linear alcohols are produced from ethylene and triethylaluminium followed by oxidation and hydrolysis. An idealized synthesis of 1-octanol is shown:

The process generates a range of alcohols that are separated by distillation.

Many higher alcohols are produced by hydroformylation of alkenes followed by hydrogenation. When applied to a terminal alkene, as is common, one typically obtains a linear alcohol:

Such processes give fatty alcohols, which are useful for detergents.

Hydration reactions
Some low molecular weight alcohols of industrial importance are produced by the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and tert-butanol are produced by this general method. Two implementations are employed, the direct and indirect methods. The direct method avoids the formation of stable intermediates, typically using acid catalysts. In the indirect method, the alkene is converted to the sulfate ester, which is subsequently hydrolyzed. The direct hydration uses ethylene (ethylene hydration) or other alkenes from cracking of fractions of distilled crude oil.

Hydration is also used industrially to produce the diol ethylene glycol from ethylene oxide.

Fermentation
Ethanol is obtained by fermentation of glucose (which is often obtained from starch) in the presence of yeast. Carbon dioxide is cogenerated. Like ethanol, butanol can be produced by fermentation processes. Saccharomyces yeast are known to produce these higher alcohols at temperatures above 75 °F. The bacterium Clostridium acetobutylicum can feed on cellulose (also an alcohol) to produce butanol on an industrial scale.

Substitution
Primary alkyl halides react with aqueous NaOH or KOH to give alcohols in nucleophilic aliphatic substitution. Secondary and especially tertiary alkyl halides will give the elimination (alkene) product instead. Grignard reagents react with carbonyl groups to give secondary and tertiary alcohols. Related reactions are the Barbier reaction and the Nozaki-Hiyama reaction.

Reduction
Aldehydes or ketones are reduced with sodium borohydride or lithium aluminium hydride (after an acidic workup). Another reduction using aluminium isopropoxide is the Meerwein-Ponndorf-Verley reduction. Noyori asymmetric hydrogenation is the asymmetric reduction of β-keto-esters.

Hydrolysis
Alkenes engage in an acid catalyzed hydration reaction using concentrated sulfuric acid as a catalyst that gives usually secondary or tertiary alcohols. Formation of a secondary alcohol via alkene reduction and hydration is shown:

 * Secondary alcohol formation-diagram.svg

The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N-bromosuccinimide and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed.

Deprotonation
With aqueous pKa values of around 16–19, alcohols are, in general, slightly weaker acids than water. With strong bases such as sodium hydride or sodium they form salts called alkoxides, with the general formula RO-M+ (where R is an alkyl and M is a metal).

The acidity of alcohols is strongly affected by solvation. In the gas phase, alcohols are more acidic than in water. In DMSO, alcohols (and water) have a pKa of around 29–32. As a consequence, alkoxides (and hydroxide) are powerful bases and nucleophiles (e.g., for the Williamson ether synthesis) in this solvent. In particular, RO- or HO- in DMSO can be used to generate significant equilibrium concentrations of acetylide ions through the deprotonation of alkynes (see Favorskii reaction).

Nucleophilic substitution
Tertiary alcohols react with hydrochloric acid to produce tertiary alkyl chloride. Primary and secondary alcohols are converted to the corresponding chlorides using thionyl chloride and various phosphorus chloride reagents.

Primary and secondary alcohols, likewise, convert to alkyl bromides using phosphorus tribromide, for example:

In the Barton-McCombie deoxygenation an alcohol is deoxygenated to an alkane with tributyltin hydride or a trimethylborane-water complex in a radical substitution reaction.

Dehydration
Meanwhile, the oxygen atom has lone pairs of nonbonded electrons that render it weakly basic in the presence of strong acids such as sulfuric acid. For example, with methanol:

Upon treatment with strong acids, alcohols undergo the E1 elimination reaction to produce alkenes. The reaction, in general, obeys Zaitsev's Rule, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols are eliminated easily at just above room temperature, but primary alcohols require a higher temperature.

This is a diagram of acid catalyzed dehydration of ethanol to produce ethylene:

A more controlled elimination reaction requires the formation of the xanthate ester.

Protonolysis
Tertiary alcohols react with strong acids to generate carbocations. The reaction is related to their dehydration, e.g. isobutylene from tert-butyl alcohol. A special kind of dehydration reaction involves triphenylmethanol and especially its amine-substituted derivatives. When treated with acid, these alcohols lose water to give stable carbocations, which are commercial dyes.

Esterification
Alcohol and carboxylic acids react in the so-called Fischer esterification. The reaction usually requires a catalyst, such as concentrated sulfuric acid:

Other types of ester are prepared in a similar manner−for example, tosyl (tosylate) esters are made by reaction of the alcohol with 4-toluenesulfonyl chloride in pyridine.

Oxidation
Primary alcohols (R\sCH2OH) can be oxidized either to aldehydes (R\sCHO) or to carboxylic acids (R\sCO2H). The oxidation of secondary alcohols (R^{1}R^{2}CH\sOH) normally terminates at the ketone (R^{1}R^{2}C\dO) stage. Tertiary alcohols (R^{1}R^{2}R^{3}C\sOH) are resistant to oxidation.

The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R\sCH(OH)2) by reaction with water before it can be further oxidized to the carboxylic acid.

Reagents useful for the transformation of primary alcohols to aldehydes are normally also suitable for the oxidation of secondary alcohols to ketones. These include Collins reagent and Dess-Martin periodinane. The direct oxidation of primary alcohols to carboxylic acids can be carried out using potassium permanganate or the Jones reagent.

license: Creative Commons - Attribution Share-Alike - https://creativecommons.org/licenses/by-sa/4.0/

title: Alcohol (chemistry)


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Achill Island

Achill Island (Acaill, Oileán Acla) is the largest of the Irish isles and lies off the west coast of Ireland in County Mayo. It had a population of 2,345 in the 2022 census. Its area is around 148 km2. Achill is attached to the mainland by Michael Davitt Bridge, between the villages of Achill Sound and Polranny. A bridge was first completed here in 1887. Other centres of population include the villages of Keel, Dooagh, Dooega, Dooniver, and Dugort. The parish's main Gaelic football pitch and secondary school are on the mainland at Polranny. Early human settlements are believed to have been established on Achill around 3000 BC. A significant geographical feature of the island is peat bog. The parish of Achill consists of Achill Island, Achillbeg, Inishbiggle and the Corraun Peninsula.

Roughly half of the island, including the villages of Achill Sound and Bun an Churraigh are in the Gaeltacht (traditional Irish-speaking region) of Ireland, although the vast majority of the island's population speaks English as their daily language.

History
It is believed that at the end of the Neolithic Period (around 4000 BC), Achill had a population of 500–1,000 people. The island would have been mostly forest until the Neolithic people began crop cultivation. Settlement increased during the Iron Age, and the dispersal of small promontory forts around the coast indicate the warlike nature of the times. Megalithic tombs and forts can be seen at Slievemore, along the Atlantic Drive and on Achillbeg.

Overlords
Achill Island lies in the Barony of Burrishoole, in the territory of ancient Umhall (Umhall Uactarach and Umhall Ioctarach), that originally encompassed an area extending from the County Galway/Mayo border to Achill Head.

The hereditary chieftains of Umhall were the O'Malleys, recorded in the area in 814 AD when they successfully repelled an onslaught by the Vikings in Clew Bay. The Anglo-Norman invasion of Connacht in 1235 AD saw the territory of Umhall taken over by the Butlers and later by the de Burgos. The Butler Lordship of Burrishoole continued into the late 14th century when Thomas le Botiller was recorded as being in possession of Akkyll and Owyll.

Immigration
In the 17th and 18th centuries, there was much migration to Achill from other parts of Ireland, particularly Ulster, due to the political and religious turmoil of the time. For a while, there were two different dialects of Irish being spoken on Achill. This led to many townlands being recorded as having two names during the 1824 Ordnance Survey, and some maps today give different names for the same place. Achill Irish still has many traces of Ulster Irish.

In the nineteenth and early twentieth centuries, seasonal migration of farm workers to East Lothian to pick potatoes took place; these squads of 'tattie howkers' were known as Achill workers, although not all were from Achill, and were organised for potato merchants by gaffers or gangers. Squads travelled from farm to farm to harvest the crop and were allocated basic accommodation. On 15 September 1937 ten young migrant potato pickers from Achill died in a fire at Kirkintilloch.

Grace O'Malley's Castle
Carrickkildavnet Castle is a 15th-century tower house associated with the O'Malley Clan, who were once a ruling family of Achill. Grace O' Malley, or Granuaile, the most famous of the O'Malleys, was born on Clare Island around 1530. Her father was the chieftain of the barony of Murrisk. The O'Malleys were a powerful seafaring family, who traded widely. Grace became a fearless leader and gained fame as a sea captain and pirate. She is reputed to have met Queen Elizabeth I in 1593. She died around 1603 and is buried in the O'Malley family tomb on Clare Island.

Achill Mission
One of Achill's most famous historical sites is that of the Achill Mission or 'the Colony' at Dugort. In 1831, the Anglican (Church of Ireland) Rev Edward Nangle founded a mission at Dugort. The Mission included schools, cottages, an orphanage, an infirmary and a guesthouse.

The Colony gave rise to mixed assessments, particularly during the Great Famine when charges of "souperism" were leveled against Nangle. The provision of food across the Achill Mission schools - which also provided 'scriptural' religious instruction - was particularly controversial.

For almost forty years, Nangle edited a newspaper called the Achill Missionary Herald and Western Witness, which was printed in Achill. He expanded his mission into Mweelin, Kilgeever, West Achill where a school, church, rectory, cottages and a training school were built. Edward's wife, Eliza, suffered poor health in Achill and died in 1852; she is buried with six of the Nangle children on the slopes of Slievemore in North Achill.

In 1848, at the height of the Great Famine, the Achill Mission published a prospectus seeking to raise funds for the acquisition of significant additional lands from Sir Richard O'Donnell. The document gives an overview, from the Mission's perspective, of its activities in Achill over the previous decade and a half including considerable sectarian unrest. In 1851, Edward Nangle confirmed the purchase of the land which made the Achill Mission the largest landowner on the island.

The Achill Mission began to decline slowly after Nangle was moved from Achill and it closed in the 1880s. When Edward Nangle died in 1883 there were opposing views on his legacy.

Railway
In 1894, the Westport – Newport railway line was extended to Achill Sound. The railway station is now a hostel. The train provided a great service to Achill, but it also is said to have fulfilled an ancient prophecy. Brian Rua O' Cearbhain had prophesied that 'carts on iron wheels' would carry bodies into Achill on their first and last journey. In 1894, the first train on the Achill railway carried the bodies of victims of the Clew Bay Drowning. This tragedy occurred when a boat overturned in Clew Bay, drowning thirty-two young people. They had been going to meet the steamer which would take them to Britain for potato picking.

The Kirkintilloch Fire in 1937 almost fulfilled the second part of the prophecy when the bodies of ten victims were carried by rail to Achill. While it was not literally the last train, the railway closed just two weeks later. These people had died in a fire in a bothy in Kirkintilloch. This term referred to the temporary accommodation provided for those who went to Scotland to pick potatoes, a migratory pattern that had been established in the early nineteenth century.

Kildamhnait
Kildamhnait on the south-east coast of Achill is named after St. Damhnait, or Dymphna, who founded a church there in the 7th century. There is also a holy well just outside the graveyard. The present church was built in the 1700s and the graveyard contains memorials to the victims of two of Achill's greatest tragedies, the Kirchintilloch Fire (1937) and the Clew Bay Drowning (1894).

The Monastery
In 1852, John MacHale, Roman Catholic Archbishop of Tuam, purchased land in Bunnacurry, on which a Franciscan Monastery was established, which, for many years, provided an education for local children. The building of the monastery was marked by a conflict between the Protestants of the mission colony and the workers building the monastery. The dispute is known in the island folklore as the Battle of the Stones.

A monk who lived at the monastery for almost thirty years was Paul Carney. He wrote a biography of James Lynchehaun who was convicted for the 1894 attack on an Englishwoman named Agnes MacDonnell, which left her face disfigured, and the burning of her home, Valley House, Tonatanvally, North Achill. The home was rebuilt and MacDonnell died there in 1923, while Lynchehaun escaped to the USA after serving 7 years and successfully resisted extradition but spent his last years in Scotland, where he died. Carney's-great grandniece, Patricia Byrne, wrote her own account of Mrs MacDonnell and Lynchehaun, entitled The Veiled Woman of Achill.

Carney also wrote accounts of his lengthy fundraising trips across the U.S. at the start of the 20th century. The ruins of this monastery are still to be seen in Bunnacurry today.

Valley House
The historic Valley House is located in Tonatanvally, "The Valley", near Dugort, in the northeast of Achill Island. The present building sits on the site of a hunting lodge built by the Earl of Cavan in the 19th century. Its notoriety arises from an incident in 1894 in which the then owner, an Englishwoman, Mrs Agnes McDonnell, was savagely beaten and the house set alight by a local man, James Lynchehaun. Lynchehaun had been employed by McDonnell as her land agent, but the two fell out and he was sacked and told to quit his accommodation on her estate. A lengthy legal battle ensued, with Lynchehaun refusing to leave. At the time, in the 1890s, the issue of land ownership in Ireland was politically charged. After the events at the Valley House in 1895, Lynchehaun would falsely claim his actions were carried out on behalf of the Irish Republican Brotherhood and motivated by politics. He escaped from custody after serving seven years and fled to the United States seeking political asylum (although Michael Davitt refused to shake his hand, calling Lynchehaun a "murderer"), where he successfully defeated legal attempts by the British authorities to have him extradited to face charges arising from the attack and the burning of the Valley House. Agnes McDonnell suffered terrible injuries from the attack but survived and lived for another 23 years, dying in 1923. Lynchehaun is said to have returned to Achill on two occasions, once in disguise as an American tourist, and eventually died in Girvan, Scotland, in 1937. The Valley House is now a hostel and bar.

The Deserted Village
Close by Dugort, at the base of Slievemore mountain lies the Deserted Village. There are approximately 80 ruined houses in the village. The houses were built of unmortared stone, which means that no cement or mortar was used to hold the stones together. Each house consisted of just one room and this room was used as a kitchen, living room, bedroom and even a stable. If one looks at the fields around the Deserted Village and right up the mountain, one can see the tracks in the fields of 'lazy beds', which is the way crops like potatoes were grown. In Achill, as in many areas of Ireland, a system called 'Rundale' was used for farming. This meant that the land around a village was rented from a landlord. This land was then shared by all the villagers to graze their cattle and sheep. Each family would then have two or three small pieces of land scattered about the village, which they used to grow crops. For many years people lived in the village and then in 1845 Famine struck in Achill as it did in the rest of Ireland. Most of the families moved to the nearby village of Dooagh, which is beside the sea, while some others emigrated. Living beside the sea meant that fish and shellfish could be used for food. The village was completely abandoned which is where the name 'Deserted Village' came from.

No one has lived in these houses since the time of the Famine, however, the families that moved to Dooagh and their descendants, continued to use the village as a 'booley village'. This means that during the summer season, the younger members of the family, teenage boys and girls, would take the cattle to graze on the hillside and they would stay in the houses of the Deserted Village. This custom continued until the 1940s. Boolying was also carried out in other areas of Achill, including Annagh on Croaghaun mountain and in Curraun. At Ailt, Kildownet, the remains of a similar deserted village can be found. This village was deserted in 1855 when the tenants were evicted by the local landlord so the land could be used for cattle grazing; the tenants were forced to rent holdings in Currane, Dooega and Slievemore. Others emigrated to America.

Archaeology

Recent archaeological research suggests the village was occupied year-round at least as early as the 19th century, though it is known to have served as a seasonally occupied 'booley village' by the first half of the 20th century. A booley village (a number of which exist in a ruined state on the island) is a village occupied only during part of the year, such as a resort community, a lake community, or (as the case on Achill) a place to live while tending flocks or herds of ruminants during winter or summer pasturing. Specifically, some of the people of Dooagh and Pollagh would migrate in the summer to Slievemore and then go back to Dooagh in the autumn. The summer 2009 field school excavated Round House 2 on Slievemore Mountain under the direction of archaeologist Stuart Rathbone. Only the outside north wall, entrance way and inside of the Round House were completely excavated.

From 2004 to 2006, the Achill Island Maritime Archaeology Project directed by Chuck Meide was sponsored by the College of William and Mary, the Institute of Maritime History, the Achill Folklife Centre (now the Achill Archaeology Centre), and the Lighthouse Archaeological Maritime Program (LAMP). This project focused on the documentation of archaeological resources related to Achill's rich maritime heritage. Maritime archaeologists recorded a 19th-century fishing station, an ice house, boat house ruins, a number of anchors which had been salvaged from the sea, 19th-century and more recent currach pens, a number of traditional vernacular watercraft including a possibly 100-year-old Achill yawl, and the remains of four historic shipwrecks.

Other places of interest
The cliffs of Croaghaun on the western end of the island are the third highest sea cliffs in Europe but are inaccessible by road. Near the westernmost point of Achill, Achill Head, is Keem Bay. Keel Beach is quite popular with tourists and some locals as a surfing location. South of Keem beach is Moytoge Head, which with its rounded appearance drops dramatically down to the ocean. An old British observation post, built during World War I to prevent the Germans from landing arms for the Irish Republican Army, is still standing on Moytoge. During the Second World War this post was rebuilt by the Irish Defence Forces as a lookout post for the Coast Watching Service wing of the Defence Forces. It operated from 1939 to 1945.

The mountain of Slievemore, (672 m) rises dramatically in the north of the island and the Atlantic Drive (along the south/west of the island) has some scenic views. On the slopes of Slievemore, there is an abandoned village, the "Deserted Village", traditionally thought to be a remnant village from An Gorta Mór (The Great Hunger of 1845–1849). Just west of the deserted village is an old Martello tower, again built by the British to warn of any possible French invasion during the Napoleonic Wars. The area also boasts an approximately 5000-year-old Neolithic tomb.

Achillbeg (Acaill Beag, Little Achill) is a small island just off Achill's southern tip. Its inhabitants were resettled on Achill in the 1960s. A plaque to Johnny Kilbane is situated on Achillbeg and was erected to celebrate 100 years since his first championship win.

The villages of Dooniver and Askill have picturesque scenery and the cycle route is popular with tourists.

Caisleán Ghráinne, also known as Kildownet Castle, is a small tower house built in the early 1400s. It is located in Cloughmore, on the south of Achill Island. It is noted for its associations with Grace O'Malley, along with the larger Rockfleet Castle in Newport.

Economy
While a number of attempts at setting up small industrial units on the island have been made, its economy is largely dependent on tourism. Subventions from Achill people working abroad allowed many families to remain living in Achill throughout the 19th and 20th centuries. In the past, fishing was a significant activity but this aspect of the economy is small now. At one stage, the island was known for its shark fishing, basking shark in particular was fished for its valuable shark liver oil. There was a big spurt of growth in tourism in the 1960s and 1970s before which life was tough and difficult on the island. Despite healthy visitor numbers each year, the common perception is that tourism in Achill has been slowly declining since its heyday. Currently, the largest employers on Achill are two hotels.

Religion
Most people on Achill are either Roman Catholic or Anglican (Church of Ireland).

Overview of the churches
 * Catholic:
 * Bunnacurry Church (Saint Josephs)
 * The Valley Church; Only open for certain events.
 * Dookinella Church
 * Currane Church
 * Pollagh Church
 * Derreens Church
 * Dooega Church
 * Belfarsed Church
 * Achill Sound Church
 * Church of Ireland:
 * Dugort Church (St. Thomas's church)
 * Innisbiggle Island church
 * Other:
 * House of Prayer, Achill

Artists
For almost two centuries, a number of artists have had a close relationship with Achill Island, including the landscape painter Paul Henry. Within the emerging Irish Free State, Paul Henry's landscapes from Achill and other areas reinforced a vision of Ireland of communities living in harmony with the land. He lived in Achill for almost a decade with his wife, artist Grace Henry and, while using similar subject-matter, the pair developed very different styles.

This relationship of artists with Achill was particularly intense in the early decades of the twentieth century when Eva O'Flaherty (1874-1963) became a focal point for artistic networking on the island. A network of over 200 artists linked to Achill is charted in "Achill Painters - An Island History" and includes painters such as the Belgian Marie Howet, the American Robert Henri, the modernist painter Mainie Jellett and contemporary artist Camille Souter.

The 2018 Coming Home Art & The Great Hunger exhibition, in partnership with The Great Hunger Museum of Quinnipiac University, USA, featured Achill's Deserted Village and the island lazy beds prominently in works by Geraldine O'Reilly and Alanna O'Kelly; also included was an 1873 painting, 'Cottage, Achill Island' by Alexander Williams - one of the first artists to open up the island to a wider audience.

Education
Hedge schools existed in most villages of Achill in various periods of history. A university was started by the missions to Achill in Mweelin. In the modern age, there used to be two secondary schools in Achill, Mc Hale College and Scoil Damhnait. However, in August 2011, the two schools amalgamated to form Coláiste Pobail Acla. For primary education, there are eight national schools including Bullsmouth NS, Valley NS, Bunnacurry NS, Dookinella NS, Dooagh NS, Saula NS, Achill Sound NS and Tonragee NS. National schools closed down include Dooega NS, Crumpaun NS, Ashleam NS and Currane NS.

Rail
Achill railway station, still on the mainland and not on the island, was opened by the Midland Great Western Railway on 13 May 1895, the terminus of its line from Westport via Newport and Mulranny. The station, and the line, were closed by the Great Southern Railways on 1 October 1937. The Great Western Greenway, created during 2010 and 2011, follows the line's route and has proved to be very successful in attracting visitors to Achill and the surrounding areas.

Road
The R319 road is the main road onto the island.

Bus
Bus Éireann's route 450 operates several times daily to Westport and Louisburgh from the island's scattered villages. Bus Éireann also provides transport for the area's secondary school children.

Cuisine
Achill Island has several bars, cafes and restaurants. The island's Atlantic location means that seafood, including lobster, mussels, salmon, trout and winkles, are common meals. With a large sheep and cow population, lamb and beef are popular on the island too.

Sport
Achill has a Gaelic football club which competes in the junior championship and division 1E of the Mayo League. There are also Achill Rovers which play in the Mayo Association Football League.

There is a 9-hole links golf course on the island. Outdoor activities can be done through Achill Outdoor Education Centre. Achill Island's rugged landscape and the surrounding ocean offers multiple locations for outdoor adventure activities, like surfing, kite-surfing and sea kayaking. Fishing and watersports are also common. Sailing regattas featuring a local vessel type, the Achill Yawl, have been popular since the 19th century, though most present-day yawls, unlike their traditional working boat ancestors, have been structurally modified to promote greater speed under sail. The island's waters and underwater sites are occasionally visited by scuba divers, though Achill's unpredictable weather generally has precluded a commercially successful recreational diving industry.

Population
In 2016, the population was 2,594, with 5.2% claiming they spoke Irish on a daily basis outside the education system. The island's population has declined from around 6,000 before the Great Famine of the mid-19th century.

Demographics
The table below reports data on Achill Island's population taken from Discover the Islands of Ireland (Alex Ritsema, Collins Press, 1999) and the census of Ireland.

Architecture
Few inhabited houses date from before the 20th century, though there are many examples of abandoned stone structures dating to the 19th century.

The best known of these earlier can be seen in the "Deserted Village" ruins near the graveyard at the foot of Slievemore. Even the houses in this village represent a relatively comfortable class of dwelling as, even as recently as a hundred years ago, some people still used "Beehive" style houses (small circular single-roomed dwellings with a hole in the ceiling to let out smoke).

Many of the oldest inhabited cottages date from the activities of the Congested Districts Board for Ireland—a body set up around the turn of the 20th century in Ireland to improve the welfare of the inhabitants of small villages and towns. Most of the homes in Achill at the time were very small and tightly packed together in villages. The CDB subsidised the building of new, more spacious (though still small by modern standards) homes outside of the traditional villages.

Notable people

 * Heinrich Böll, German writer who spent several summers with his family and later lived several months per year on the island
 * Charles Boycott (1832–1897), unpopular landowner from whom the term boycott arose
 * Nancy Corrigan, pioneer aviator, second female commercial pilot in the US.
 * Dermot Freyer (1883–1970), writer who opened a hotel on the island
 * Paul Henry, artist, stayed on the island for a number of years in the early 1900s
 * James Kilbane, singer, lives on the island
 * Johnny Kilbane, boxer
 * Saoirse McHugh, former Green Party politician
 * Danny McNamara, musician
 * Richard McNamara, musician
 * Eva O'Flaherty, Nationalist, model and milliner
 * Thomas Patten, from Dooega. Died during the Siege of Madrid in December 1936
 * Honor Tracy, author, lived there until her death in 1989

Literature

 * Heinrich Böll: Irisches Tagebuch, Berlin, 1957
 * Bob Kingston The Deserted Village at Slievemore, Castlebar, 1990
 * Theresa McDonald: Achill: 5000 B.C. to 1900 A.D.: Archeology History Folklore, I.A.S. Publications [1992]
 * Rosa Meehan: The Story of Mayo, Castlebar, 2003
 * James Carney: The Playboy & the Yellow lady, 1986 Poolbeg
 * Hugo Hamilton: The Island of Talking, 2007
 * Kevin Barry: Beatlebone, 2015
 * Mealla Nī Ghiobúin: Dugort, Achill Island 1831–1861: The Rise and Fall of a Missionary Community, 2001
 * Patricia Byrne: The Veiled Woman of Achill – Island Outrage & A Playboy Drama, 2012
 * Mary J. Murphy: Achill's Eva O'Flaherty – Forgotten Island Heroine, 2011
 * Patricia Byrne: The Preacher and The Prelate – The Achill Mission Colony and The Battle for Souls in Famine Ireland, 2018
 * Mary J. Murphy, Achill Painters -An Island History, 2020
 * Michael Gallagher, Stick on Stone, 2013

In popular culture
The island is featured throughout the film The Banshees of Inisherin in various locations on the island including Keem Bay, Cloughmore, and Purteen Pier.

The film My Sailor My Love features Achill island.

The island is the primary setting of the visual novel If Found....

title: Achill Island