Organic Chemistry Ch 9. Carboxylic Acid Derivatives

Question 1

Amides

Answer 1

Condensation products of carboxylic acids and ammonia or amines, given the suffix -amide, the alkyl groups on a substituted amide are written at the beginning of the name with the prefix N-

Question 2

Lactams

Answer 2

Cyclic amides, named by the greek letter of the carbon forming the bond with the nitrogen

Question 3

Esters

Answer 3

Condensation products of carboxylic acids with alcohols, given the suffix -oate and the esterifying group is written as a substituent without a number

Question 4

Fisher esterification

Answer 4

Condensation of carboxylic acids with alcohols

Question 5

Lactones

Answer 5

Cyclic esters, named by the number of carbons in the ring and the Greek letter of the carbon forming the bond with the oxygen

Question 6

Triacylglycerols

Answer 6

Form of fat storage which includes three ester bonds between glycerol and fatty acids

Question 7

Saponification

Answer 7

The breakdown of fat using a strong base to form soap (salts of long-chain carboxylic acids)

Question 8

Soap

Answer 8

Salts of long chain carboxylic acids

Question 9

Anhydrides

Answer 9

Condensation dimers of carboxylic acids, symmetric anhydrides are named for the parent carboxylic acid followed by anhydride, asymmetric anhydrides are named by listing the parent carboxylic acids alphabetically followed by anhydride

Question 10

Cyclic anhydrides

Answer 10

Can be synthesized by heating dioic acids, five or six membered rings are generally stable

Question 11

Reactivity of carboxylic acid derivatives

Answer 11

In nucleophilic substitution reactions, anhydrides are more reactive esters, which are more reactive than amides

Question 12

Steric hindrance

Answer 12

Describes when a reaction cannot proceed (or significantly slows) because of substituents crowding the reactive site, can be taken advantage of to protect groups

Question 13

Protecting groups

Answer 13

Can be used to increase steric hindrance or otherwise decrease the reactivity of a particular portion of a molecule, includes acetals

Question 14

Induction

Answer 14

Refers to the uneven distribution of charge across a sigma bond because the differences in electronegativity, more electronegative groups in a carbonyl containing compound, the greater its reactivity

Question 15

Conjugation

Answer 15

Refers to the presence of alternating single and multiple bonds which creates delocalized pi electron clouds above and below the plane of the molecule, conjugated carbonyl containing compounds are more reactive because they can stabilize their transition states

Question 16

Resonance

Answer 16

Electrons experience resonance through the unhybridized p orbitals, increases stability

Question 17

Strain and reactivity

Answer 17

Increased strain in a molecule can make it more reactive

Question 18

Beta-lactams reactivity

Answer 18

Prone to hydrolysis because they have significant ring strain

Question 19

Ring strain

Answer 19

Due to torsional strain from eclipsing interactions and angle strain from compressing bond angles below 109.5 degrees

Question 20

Carboxylic acid derivatives and nucleophilic acyl substitutions

Answer 20

All carboxylic acid derivatives can undergo nucleophilic substitution reactions, the rates at which they do so are determined by their relative reactivities

Question 21

Anhydrides nucleophilic acyl substitutions

Answer 21

Anhydrides can be cleaved by the addition of a nucleophile

Addition of ammonia or an amine results in an amide and a carboxylic acid
Addition of an alcohol results in an ester and a carboxylic acid
Addition of water results in two carboxylic acids

Question 22

Transesterification

Answer 22

The exchange of one esterifying group for another on an ester, the attacking nucleophile is an alcohol

Question 23

Amide hydrolysis

Answer 23

Amides can be hydrolyzed to carboxylic acids under strongly acidic or basic conditions, the attacking nucleophile is water or the hydroxide anion