Carboxylic Acids

Question 1

contain a carbonyl and hydroxyl group connected to the same carbon; always terminal groups; polar and hydrogen bond very well resulting in high boiling points; often exist as dimers in solution; acidity is enhanced by resonance between its oxygen atoms and substituents that are electron withdrawing; acidity decreased by substituents that are electron donating

Answer 1

carboxylic acids

Question 2

carboxylic acids that have an α-hydrogen that is highly acidic

Answer 2

β-dicarboxylic acids

Question 3

common reaction carboxylic acids; after opening the carbonyl via nucleophilic attack and forming a tetrahedral intermediate, the carbonyl can reform, thereby kicking off the leaving group; nucleophilic molecule replaces the leaving group of an acyl derivative; reactions are favored by a good leaving group

Answer 3

nucleophilic acyl substitution

Question 4

encompass all molecules with a carboxylic acid-derived carbonyl, including carboxylic acids, amides, esters, and anhydrides

Answer 4

acyl derivatives

Question 5

nucleophilic acyl substitution:

is formed if nucleophile is ammonia or amine

Answer 5

amide

Question 6

nucleophilic acyl substitution:

is formed if nucleophile is an alcohol

Answer 6

ester

Question 7

nucleophilic acyl substitution:

is formed if nucleophile is another carboxylic acid

Answer 7

anhydride

Question 8

nucleophilic acyl substitution reaction:

Answer 8

Question 9

strong reducing agent that can be used to reduce carboxylic acids to a primary alcohol; NaBH4 (sodium borohydride) is not strong enough

Answer 9

LiAlH4 (lithium aluminum hydride, LAH)

Question 10

spontaneous loss of carbon as carbon dioxide when heating by β-dicarboxylic acids and other β-keto acids; reaction proceeds via six-membered cyclic intermediate

Answer 10

decarboxylation

Question 11

decarboxylation mechanism:

Answer 11

Question 12

mixing long-chain carboxylic acids (fatty acids) with a strong base results in formation of a salt we call soap

Answer 12

saponification

Question 13

contain hydrophilic carboxylate heads and hydrophobic alkyl chain tails; organize in hydrophilic environments to from micelles

Answer 13

soaps

Question 14

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

Answer 14

micelle