Organic Chemistry Chapter 9: Carboxylic Acid Derivatives

Question 1

Amides

Answer 1

the condensation produce of carboxylic acids and ammonia or amines

Question 2

Amides suffix

Answer 2

-amide

Question 3

What are the alkyl group on a substituted amide denoted with?

Answer 3

N-

Question 4

Cyclic amides are called

Answer 4

lactams - named by the greek letter of the carbon forming the bond with the nitrogen

Question 5

Esters

Answer 5

condensation products of carboxylic acids with alcohols (fisher esterification)

Question 6

Ester suffix

Answer 6

-oate

Question 7

Cyclic esters

Answer 7

lactones - named by the number of carbons in the ring and the Greek letter of the carbon forming the bond with the oxygen.

Question 8

Tracylglycerols

Answer 8

form of fat storage that contain three ester bonds between glycerol and fatty acids

Question 9

Saponification

Answer 9

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

Question 10

Anhydrides

Answer 10

condensation dimers of carboxylic acids

Question 11

Symmetric anhydrides are named for:

Answer 11

the parent carboxylic acid, followed by anhydride

Question 12

Asymmetric anhydrides are named:

Answer 12

by listing the parent carboxylic acids alphabetically, followed by anhydride.

Question 13

How can cyclic anhydrides be synthesized?

Answer 13

By heating dioic acids. Five or six-membered rings are generally stable.

Question 14

In nucleophilic substitution reactions, which is most reactive?

Anhydride, amides, esters

Answer 14

Anhydride, esters, amides

Question 15

Steric hindrance

Answer 15

describes when a reaction cannot proceed (or significantly slows because of substituents crowding the reactive site.

Question 16

Protecting groups

Answer 16

can be used to increase steric hindrance or otherwise decrease the reactivity of a particular portion of a molecule

Question 17

Induction

Answer 17

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

Question 18

Conjugation

Answer 18

refers to the presence of alternating single and multiple bonds, which creates delocalized pi electron clouds above and below the plane of the molecule.

Question 19

Resonance

Answer 19

experienced through the unhybridized p-orbitals, increasing stability. Conjugated carbonyl-containing compounds are more reactive because they can stabilize their transition states.

Question 20

Increased strain can

Answer 20

make it more reactive (ex. B-lactams are prone to hydrolysis because they have significant ring strain.

Question 21

Ring strain

Answer 21

is due to torsional strain from eclipsing interactions and angle strain from compressing bond angles below 109.5

Question 22

How can anhydrides be cleaved?

Answer 22

an addition of a nucleophile.

Question 23

Anhydride + ammonia or amine

Answer 23

results in an amide and a carboxylic acid

Question 24

Anhydride + alcohol

Answer 24

ester and a carboxylic acid

Question 25

Anhydride + water

Answer 25

2 carboxylic acids

Question 26

Transesterification

Answer 26

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

Question 27

Amides can be hydrolyzed to carboxylic acids under

Answer 27

strongly acidic or basic conditions. The attacking nucleophile is water or the hydroxide anion.