Organic Chemistry Ch 8. Carboxylic Acids

Question 1

Carboxylic acids

Answer 1

Contain a carbonyl and a hydroxyl group connected to the same carbon, they are always terminal groups, indicated with the suffix -oic acid, salts are named with the suffix -oate and dicarboxylic acids are -dioic acid

Question 2

Physical properties of carboxylic acids

Answer 2

Are polar and a hydrogen bond very well, resulting in a high boiling point, often exist as dimers in solution, acidity is enhanced by the residence between the oxygen atoms, acidity can be further enhanced by substituents that are electron withdrawing and decreased by substituents that are electron donating

Question 3

Dimers

Answer 3

-

Question 4

Beta-dicarboxylic acids

Answer 4

Have an alpha hydrogen that is highly acidic

Question 5

Carboxylic acid from alcohol

Answer 5

Can be made by the oxidation of primary alcohols or aldehydes using an oxidizing agent like potassium permanganate, dichromate salts, or chromium trioxide

Question 6

Nucleophilic acyl substitution

Answer 6

A common reaction for carboxylic acids, a nucleophile attacks the electrophilic carbonyl carbon opening the carbonyl and forming a tetrahedral intermediate, the carbonyl reforms kicking off the leaving group

If nucleophile ammonia or an amine, an amide is formed

If nucleophile an alcohol, an ester is formed

If nucleophile is another carboxylic acid, and anhydride is formed

Question 7

Amide

Answer 7

Formed from nucleophilic acyl substitution in which the nucleophile is ammonia or an amine, given the suffix -amide

Question 8

Lactams

Answer 8

Circular amides

Question 9

Ester

Answer 9

Formed from nucleophilic acyl substitution in which the nucleophile is an alcohol, given the suffix -oate

Question 10

Lactones

Answer 10

Cyclic esters

Question 11

Anhydride

Answer 11

Formed from nucleophilic acyl substitution in which the nucleophile is another carboxylic acid, given the suffix anhydride for both linear and cyclic anhydrides

Question 12

Carboxylic acid reduction

Answer 12

Can be reduced to a primary alcohol with a strong reducing agent like lithium aluminum hydride, aldehyde intermediates form but are also reduced, will NOT be reduced by sodium borohydride

Question 13

Carboxylic acid sodium borohydride

Answer 13

Will not reduce

Question 14

Sodium borohydride

Answer 14

Common reducing agent but not strong enough to reduce a carboxylic acid

Question 15

Decarboxylation

Answer 15

Undergone by beta-dicarboxylic acids and other beta-keto acids spontaneously when heating, lose a carbon as carbon dioxide, reaction proceeds via a six-membered cyclic intermediate

Question 16

Soap

Answer 16

Salt formed by mixing long chain carboxylic acids (fatty chains) with a strong base, contain hydrophilic carboxylate heads and hydrophilic alkyl chain tails, organize in hydrophilic environments to form micelle

Question 17

Saponification

Answer 17

Mixing long chain carboxylic acids (fatty acids) with a strong base to form a salt called soap

Question 18

Micelle

Answer 18

Dissolves nonpolar organic molecules in its interior and can be solvated with water due to its exterior shell of hydrophilic groups