Download Carboxylic Acids and Derivatives: Properties, Nomenclature, and Synthesis - Prof. Roman E. and more Study notes Biology in PDF only on Docsity! Carboxylic Acids 1. -OH group added to carbonyl group produces carboxyl group 2. May be attached to alkyl or aromatic ethanoic acid methanoic acid (acetic acid) (formic acid) Carboxylic Acid Nomenclature 1. Longest C chain with carboxyl group is parent chain 2. Replace -e in parent name with -oic acid 3. Carboxyl C is C1 4. Number & name side groups appropriately Carboxylic Acid Properties 1. Solubility 2. Ionization 3. Neutralization Carboxylic Acid Solubility 1. Hydroxyl group and carbonyl group polar 2. Short chain carboxylic acids, C1 to C4 are very water soluble 3. Long chain carboxylic acids, C5 and up are slightly water soluble Carboxylic Acid Ionization 1. Donate H+ to H2O to form H3O + 2. Weak acids, but > phenols 3. Negative ion is referred to as carboxylate ion Neutralization methanoic sodium methanoate acid (sodium formate) benzoic acid sodium benzoate Organic Salts copper ( I ) naphthalate benzyl ammonium chloride Esters 1. Carboxylic acid & alcohol produce ester 2. Requires #T & H+, usually H2SO4 3. -OH from carboxylic acid and -H from alcohol produce H2O 4. Found in many plants, taste & smell Ester Hydrolysis 1. Acid hydrolysis 2. Base hydrolysis Acid hydrolysis 1. Produces carboxylic acid and alcohol methyl benzoic methanol benzoate acid Base hydrolysis 1. Saponification- produces salt of carboxylic acid (soap) & alcohol methyl sodium methanol propanoate propanoate Amine Nomenclature 1. Longest/largest carbon chain/ring is parent , N-C is C1 2. Remaining alkyl or aromatic groups attached to N, named as N- substituents 3. If identical, use di- & tri- 4. If different, arrange alphabetically Amine Nomenclature Examples
CH,CH,—NH—CH, oi
N-methylethylamine H,C—N—CH.CH,
(ethylmethylamine) N,N-dimethylethylamine
Mt
CH,CH,CHCH,
1-methylbutylamine
(2-aminobutane)
Aromatic Amines
on aN ork
aniline
N-methylaniline
Amine Reactions
1. lonization
yam Nee ihc 1e celal
3. Amidation
Amine Ionization 1. Amines are weak bases, N atom’s e- pair accepts H+ ion aminomethane methylammonium (methylamine) ion Amine Neutralization 1. Amine & inorganic acid produce ammonium salt aminomethane methylammonium chloride Amidation Example2 ethanoic aminomethane N-methylethanamide acid (methylamine) (N-methyl acetamide) (acetic acid) Amide Examples
O
a ee
—C-C-C-N-
ee |
propanamide
O
ee ee ee |
—C-C-C-N-C-—
1 |
N-methylpropanamide
Amide Nomenclature 1. Name parent amine as alkyl using N to show position 2. Carbonyl C is C1 3. Rename parent acid as amide 4. Use two N,N, if more than one carbon chain/ring attached to N 5. If identical, use di- & tri- 6. If different, arrange alphabetically Acid Hydrolysis of Amide 1. Amide, inorganic acid, & H2O produces carboxylic acid & ammonium salt ethanoic acid (acetic acid) ethanamide ammonium (acetamide) chloride Base Hydrolysis of Amide 1. Amide & base produces carboxylate salt & ammonia or alkylamine sodium propanoate N-methylpropanamide aminomethane
