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Organic chemistry and biochemistry Bashayer Alrashidi PAAET College of Nursing Thi s Photo by Unknown Author i s l icensed under CC BY-SA  Chapter 2: Alcohols, ethers, thioalcohols (thiols), amines and amides  Organic Compounds...

Organic chemistry and biochemistry Bashayer Alrashidi PAAET College of Nursing Thi s Photo by Unknown Author i s l icensed under CC BY-SA  Chapter 2: Alcohols, ethers, thioalcohols (thiols), amines and amides  Organic Compounds (Hydrocarbons) Hydrocarbon group or Alkyl group (R) R-OH O Alcohol R-C-NH2 Amide R-SH R-NH2 Thiol Amine R-O-R Ether  Alcohol - Alcohol is a derivative of water (H2O) in which one hydrogen atom is replaced with hydrocarbon group (R group). R- OH hydroxyl group - If OH (hydroxyl) group is attached to benzene, the structure will be phenol Types of alcohols: 1) Primary alcohol (10): R-CH2OH OH 2) Secondary alcohol (2 0): R-CH-R OH 3) Tertiary alcohol (3 0): R-C-R R Write 10, 20, 30, dihydric or trihydric alcohols for the following organic structures: CH3-CH-CH3 OH OH OH CH3-C-CH3 OH Naming Alcohols:.‫ تأخذ أقل رقم‬C-OH ‫( ترقيم أطول سلسة و‬1.OH ‫( و رقم الكربونة المتصله بال‬ol( ‫( نكتب نهاية اإلسم‬2 CH2-CH3 CH3-CH-CH-CH3 OH Boiling point of alcohol - B.P of alcohol is higher than hydrocarbon because of strong intermolecular bonds resulting from hydrogen bonding of hydroxyl (OH) group of alcohol. - The higher the number of OH groups in alcohol, the higher B.P of alcohol because the number of hydrogen bonds are increased. B.P of trihydric alcohol (3 OH) > B.P of dihydric alcohol (2 OH) > B.P alcohol (1 OH) Preparation of alcohol 1) Hydration of alkene (water addition reaction) CH2=CH2 + H2O CH3-CH=CH2 + H2O C=C. ‫متصلة بال‬H ‫ألكثر‬H ‫ نضيف‬:‫مالحظة‬ Oxidation of alcohols 1) Primary alcohol (0) R-CH2-OH R-CHO (Aldehyde) Enzyme catalyst (O) R-CH2-OH R-COOH ( carboxylic acid) KMO4 or CrO3 2) Secondary alcohol OH O (O) R-CH-R R-C-R (Ketone) KMO4 3) Tertiary alcohol OH (O) R-C-R No reaction, why? R  Ethers -Ether is a derivative of water in which two hydrogen atoms are replaced with hydrocarbon group (R group) R-O-R Ether R-O-R Alcohol R-OH Boiling point (B.P) Lower because has no Higher because has OH OH group (no hydrogen group (hydrogen bond). bond). Reactivity Lower reactivity (inert) More reactive because of because has no OH OH group. group. Note: B.P of alcohol (R-OH) > B.P of ether (R-O-R) > B.P of hydrocarbon (R).  Nomenclature of ethers: Ether ‫ نكتب اخر االسم‬-.‫ ترتيب هجائي‬R-groups ‫ نرتب‬-.R groups ‫ عند تكرار‬tri ‫ أو‬di ‫ نكتب‬- Example: Name the following structures 1) CH3-CH2-O-CH2-CH3 2) CH3-O-CH2-CH3 Preparation of ether from alcohol H2SO4 2 ROH ROR 140 oC H2SO4 CH3-CH2-OH + OH-CH2-CH3 140 oC Thiol or thioalcohols R-SH sulfhydryl group Amines - Are derivatives of ammonia (NH3) R-NH2 10 Amine H R-N-R 20 Amine R R-N-R 30 Amine Nomenclature of Amines Amine ‫ نكتب اخر اإلسم‬- ‫ترتيب هجائي‬R- groups ‫ نرتب‬-.R groups ‫ عند تكرار‬tri ‫ أو‬di ‫ نكتب‬- CH3 1) CH3-N-CH3 2) CH3-NH-CH2-CH3 Amides O - Nitrogen atom (N) is bounded to carbon-oxygen double bond (C or carbonyl group) O R-C-NH2 - Amides have the highest boiling points comparing to other organic compounds. B.P of amides > B.P of alcohol > B.P of ether > B.P of hydrocarbons