Carboxylic Acids and derivatives

Question 1

Anhydrides

Formation

Answer 1

Products of condensation reactions between two carboxylic acids.

Question 2

Anhydrides

Nomenclature

Answer 2

Named by sequencing the parent carboxylic acids alphabetically plus “anhydride”
Example: propanoic acid + ethanoic acid => ethanoic propanoic anhydride

Question 3

Anhydrides

Nucleophilic substitution

Answer 3

Can undergo cleavage by a nucleophile with several possible products.
Example: cleavage by H2O results in two carboxylic acids.

Question 4

Anhydrides

Reaction with amines

Answer 4

Anhydrides combine with amines to generate amides and carboxylic acids

Question 5

Esters

Answer 5

Compounds derived from carboxylic acids, where the -OH group is replaced by a -OR group. R group is any alkyl group

Question 6

Esters

Formation

Answer 6

Products of the Fischer esterification reaction which takes place between carboxylic acids and alcohols.

Question 7

Esters

Nomenclature

Answer 7

Named with the suffix -oate. Cyclic esters are named lactones.

Question 8

Esters

Saponification

Answer 8

Refers to the ester hydrolysis of fat using a strong base.

Question 9

Esters

Nucleophilic substitution

Answer 9

Can be attacked by a nucleophilic alcohol to undergo transesterification (exchange of ester groups)

Question 10

Carboxylic Acid Reactions

Nucleophilic acyl substitution

Answer 10

The carbonyl group carbon is electrophilic.
In various substitution reactions, this carbon undergoes nucleophilic attack resulting in departure of a leaving group.

Question 11

Carboxylic Acid Reactions

Nucleophilic substitution products

Answer 11

Carboxylic acid + ammonia = amide

Carboxylic acid + alcohol = ester

Carboxylic acid + carboxylic acid = anhydride

Question 12

Carboxylic Acid Reactions

Decarboxylation

Answer 12

Spontaneous loss of a carbon, catalyzed by heat. Releases CO2.
Link to biochem: pyruvate decarboxylation is part of the link step between glycolysis and the Krebs cycle.

Question 13

Carboxylic Acids

Answer 13

Contain a carbon connected to both a carbonyl C=O group and a hydroxyl -OH group.

Question 14

Carboxylic Acids

Nomenclature

Answer 14

Named with the suffix -oic acid

Question 15

Carboxylic Acids

Formation

Answer 15

Formed by oxidation of primary alcohols or aldehydes by a strong agent like KMnO4.

Question 16

Carboxylic Acids

Reduction

Answer 16

Can be reduced by hydrides like LiAlH4 to form a primary alcohol.

Question 17

Amides

Answer 17

Compounds containing a NH-C=O group

Question 18

Amides

Formation

Answer 18

Products of a condensation reaction between carboxylic acid derivatives (with good leaving groups) and amines.
For example, Cl-C=O plus -NH2 will form an amide

Question 19

Amides

Nomenclature

Answer 19

Given the suffix -amide. Cyclic amides are named lactams.

Question 20

Amides

Nucleophilic substitution

Answer 20

Can undergo a hydrolysis reaction to form carboxylic acid under conditions of high temperatures, high acidity/basicity.