Historical Development of Organic Chemistry PDF

Historical Development of Organic Chemistry Quarter 1 – Module 2 – Week 2 APPLIED CHEMISTRY BY LENIE O. JANDOC ANSHS, T - III MOST ESSENTIAL LEARNING COMPETENCY 2 Trace the historical development of organic...

Historical Development of Organic Chemistry Quarter 1 – Module 2 – Week 2 APPLIED CHEMISTRY BY LENIE O. JANDOC ANSHS, T - III MOST ESSENTIAL LEARNING COMPETENCY 2 Trace the historical development of organic chemistry. (Q1 WK2) this is for ANSHS use only 10/11/2020 LEARNING OBJECTIVES 3 After going through this module, you are expected to: 1. define organic chemistry; 2. trace historical development of organic chemistry; and 3. appreciate important contributions of development in organic chemistry to the science world this is for ANSHS use only 10/11/2020 LESSON PROPER 4 ⚫ORGANIC CHEMISTRY ⚫HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY this is for ANSHS use only 10/11/2020 ORGANIC CHEMISTRY 5 ⚫Organic chemistry deals with the study of structure, properties and reactions of organic compounds containing carbon atom. ⚫Organic reactions are used for synthesis of natural products, drugs and polymers. this is for ANSHS use only 10/11/2020 ORGANIC CHEMISTRY 6 ⚫The most commonly studied chemicals in organic chemistry are hydrocarbons (compounds with only C & H) as well as compounds based on carbon but with also contains other elements such as oxygen, nitrogen, sulfur, phosphorus and the halogens. this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 7 ⚫JONS JAKOB BERZELIUS (1779- 1848) ✔Structural isomerism of carbon atoms ✔ formic acid (ants), salicylic acid (willow bark), urea (urine) ✔Vitalism (1822) a doctrine that says the functions of a living organism are due to vital principle distinct from physicochemical process. this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 8 ⚫JUSTUS VON LIEBIG (1803- 1873) & FRIEDRICH WOHLER (1800-1882) ✔Emergence of organic chemistry in 19th century ✔ Liebig’s important contribution is the measurement of the quantities of carbon (C), hydrogen (H), and nitrogen (N) in organic compounds ✔Increasing soil fertility and yield through artificial fertilizers this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 9 ⚫JUSTUS VON LIEBIG (1803- 1873) & FRIEDRICH WOHLER (1800-1882) ✔ Wohler’s best known contribution is synthesis of urea (organic compound) using ammonium cyanate ✔ Liebig and Wohler determined the content of molecules but did not show how their elements were arranged this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 10 ⚫JEAN – BAPTISTE ANDRE DUMAS (1800- 1884) ✔ He together with Liebig pioneered radical theory ✔ Radicals were stable group of elements that were joined together to produce an electropositive group joined to an electronegative atom to form a compound ✔ Dumas covert acetic acid to trichloroacetic acid via substitution this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 11 ⚫AUGUSTE LAURENT (1808- 1853), CHARLES FREDERIC GERHARDT (1816- 1856), HERMAN KOPP (1817-1892) ✔ Laurent & Gerhardt are students of Dumas who proposed the type theory ✔ Organic substances were derived from simple molecules by substitution this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 12 ⚫AUGUSTE LAURENT (1808- 1853) ✔ Introduced concept of 2 homologous series( group of similar compounds that differed by a single unit) – 1st three members of alkane series – methane, ethane, propane this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 13 ⚫HERMAN KOPP (1817-1892) ✔ showed that each additional CH2 increases the boiling point this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 14 ⚫CHARLES FREDERIC GERHARDT (1816-1856) ✔ Introduced the ammonia (NH3), hydrogen (H2), hydrogen chloride (HCl) types ✔ “By exchanging their hydrogen among certain groups, these types give rise to acids, alcohols, ethers, hydrides, radicals, organic chlorides, acetones and alkalis” this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 15 ⚫ALEXANDER WILLIAMSON (1824- 1904) ✔ proved the existence of water type in 1850 when he synthesize diethyl ether from potassium salt of ethyl alcohol and ethyl iodide. this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 16 ⚫EDWARD FRANKLAND (1825 - 1896) ✔ Frankland with Kekule developed the concept of valence (combining power of an element) ✔ synthesized hydrocarbon radical ethyl (C2H5) by reacting ethyl iodide with zinc and produced butane with diethyl zinc ✔ proposed that in/organic compounds both had 5 combining power (valence) ✔ recognized multiple valences PCl3 & PCl5 with 3 & 5 valences this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 17 ⚫AUGUST KEKULE (1829- 1896) ✔ hypothesized that carbon was tetravalent (could combine with four substituents to form organic compounds) ✔ proposed (1858) that carbon could form chains by using some of its valences to bond to other carbon atoms ✔responsible for establishment of benzene structure this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 18 ⚫ARCHIBALD SCOTT COUPER (1831- 1892) ✔ drew formula for molecules that used dotted lines to represent the bonds between carbon atoms this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 19 ⚫ALEXANDER CRUM BROWN (1838- 1922) ✔ introduced the graphical structural formulas of compounds ✔ initially he wrote C, H, O with circles around them connected with solid lines, with the number of lines equal to the valence (almost same with LEDS) this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 20 ⚫LOUIS PASTEUR (1822- 1895), JACOBUS VAN’T HOFF (1852- 1911), JOSEPH- ACHILLE LE BEL (1847- 1930) ✔ introduced the three- dimensional nature of organic compounds ✔ Pasteur studied tartaric acid (natural tartaric acid – rotated the polarization plane of light, racemic acid – did not) ✔ STEREOISOMERISM caused by either tetravalency of carbon itself or orientation of carbon this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 21 ⚫JACOBUS VAN’T HOFF (1852- 1911) ✔explained (in 1875) stereoisomerism by proposing that the four carbon valences were on the apexes of a tetrahedron ✔ four different substituents bonded to the central carbon atom could produce two structures that were mirror images of each other this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 22 ⚫JOSEPH- ACHILLE LE BEL (1847- 1930) ✔With four different substituents, an asymmetry is produced in which the mirror is no longer super- imposable on the original this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 23 ⚫EILHARD MITSCHERLICH (1794-1863) ✔1844 reported that sodium-ammonium salts of tartaric acid and racemic acid were in every aspect except their interaction with plane- polarized light this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 24 ⚫EMIL FISCHER (1852- 1919) ✔first studied stereoisomers of glucose molecules with three centers of asymmetry ✔ 1930s, Kekule proposed that isomers has two forms that differs only by location of single and double bonds (basis of aromatic chemistry and molecular orbital theory) this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 25 ⚫AUGUST WILHELM HOFMANN (1818- 1892) ✔ examined the constituents of coal tar ✔ coal tar’s major components were aromatic hydrocarbons (benzene) ✔ isolated 20 different substances from coal tar: aniline, ammonia, phenol (first antiseptics) this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 26 ⚫AUGUST WILHELM HOFMANN (1818- 1892) ✔ examined the constituents of coal tar ✔ coal tar’s major components were aromatic hydrocarbons (benzene) ✔ isolated 20 different substances from coal tar: aniline, ammonia, phenol (first antiseptics) this is for ANSHS use only 10/11/2020  27 Image Source: https://www.google.com/search?q=is+coal+tar+same+in+asphalt+used+in+railways%3F&tbm=isch&ved=2ahUKEwjJq82JpvSAAxVeTGwGHYJwCFsQ2- cCegQIABAA&oq=is+coal+tar+same+in+asphalt+used+in+railways%3F&gs_lcp=CgNpbWcQAzoHCAAQGBCABDoHCAAQigUQQzoICAAQgAQQsQM6BQgAEIAEOgQIABADOgsIABCABBCxAxCDAToGCAAQCBAeUNARWOR6YOWEAWg BcAB4AIAB0AGIAbo0kgEGMC40Ni4xmAEAoAEBqgELZ3dzLXdpei1pbWfAAQE&sclient=img&ei=8sbmZMnqJN6YseMPguGh2AU&bih=521&biw=1024&hl=en&safe=active&ssui=on#imgrc=YAZ3h1FHbRcq0M this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 28 ⚫WILLIAM HENRY PERKIN ⚫(1838- 1907) ✔ tried to synthesized quinine, a drug to treat malaria but he failed ✔ used aniline dissolved in alcohol producing purple solution (dyed silk – mauve or purple dye) this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 29 ⚫WILLIAM HENRY PERKIN ⚫(1838- 1907) ✔ his discovery created a breakthrough since Britain became the center of the synthetic organic chemical industry this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 30 ⚫HERMANN KOLBE ✔ 1853, he synthesized salicylic acid derived from willow bark ✔ salicylic acid is known for its pain-relieving abilities this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 31 ⚫ PAUL ERLICH (1854- 1915) ✔ his best known work was on syphilis, caused by a spirochete type of bacterium ✔ synthesized series of organoarsenic compounds ✔ Neosalvarsan this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 32 ⚫ PAUL ERLICH (1854- 1915) SYPHILIS ✔a sexually transmitted infectious (STI) disease caused by the bacterium Treponema pallidum ✔this bacterium causes infection when it gets into broken skin or mucus membranes, usually of the genitals ✔most often transmitted through sexual contact, although it also can be transmitted in other ways this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 33 ✔ Protonsil patented in 1932 by Bayer division, first synthetic antibacterial against streptococcal & staphylococcal bacteria ✔ Staphylococci form clumps, whereas Streptococci grow in chains. this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC RHINOSINUSITIS FOUNDATION OF ORGANIC CHEMISTRY 34 Image Source: https://www.google.com/search?sca_esv=559602811&q=streptococcal+and+staphylococcal+bacteria&tbm=isch&source=lnms&sa=X&ved=2ahUKEwi4r- mDqfSAAxWW3TgGHQlxARYQ0pQJegQICxAB&biw=1024&bih=521&dpr=1.88&safe=active&ssui=on#imgrc=WaiaJ_wKyGD25M this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 35 this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 36 ✔Penicillin first used in 1942 an antibacterial medicine for military use only this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 37 ✔ DDT (dichloro-diphenyl- trichloroethane) was used against pests that carries disease like malaria during the World War II ✔widely used as component of insect repellents this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 38 JAMES YOUNG (1811- 1883) ✔heated coal producing liquid with distillation & purification process produced an illuminant called kerosene this is for ANSHS use only 10/11/2020  HISTORICAL BACKGROUND AND SCIENTIFIC FOUNDATION OF ORGANIC CHEMISTRY 39 19th century – synthesis of new molecules and structure of natural products 20th century – focused on the reactions of organic molecules (chem. rxns) this is for ANSHS use only 10/11/2020  CATEGORY OF DISCOVERIES BASED ON ITS SOURCES 40 A. Carbonized organic matter B. Living Organisms C. Inventions this is for ANSHS use only 10/11/2020  CATEGORY OF DISCOVERIES BASED ON ITS SOURCES 41 A. Carbonized organic matter *gasoline *oil *coal *diesel *natural gas *fossil fuels this is for ANSHS use only 10/11/2020  CATEGORY OF DISCOVERIES BASED ON ITS SOURCES 42 B. Living Organisms *natural dyes *flavorings (banana, vanilla) *scent or aroma (flowers, herbs, some part of plants, animals) this is for ANSHS use only 10/11/2020  CATEGORY OF DISCOVERIES BASED ON ITS SOURCES 43 C. Inventions *medicine (aspirin, antibiotics) *acetic acid used in vinegar *fertilizers *ethyl alcohol this is for ANSHS use only 10/11/2020 TASKS TO ACCOMPLISH 44 Formative test (can be accessed via Google Form and is posted in Google Classroom) Summative Test #1 (can be accessed via Google Form and is posted in the Google Classwork) Performance Task #2 (can be accessed in PDF and is posted in the Google Classwork) this is for ANSHS use only 10/11/2020  45 THANK YOU VERY MUCH! this is for ANSHS use only 10/11/2020