Organic Chemistry Chapter 9: Carboxylic Acid Derivatives Flashcards Preview

MCAT Gen Chem and O Chem > Organic Chemistry Chapter 9: Carboxylic Acid Derivatives > Flashcards

Flashcards in Organic Chemistry Chapter 9: Carboxylic Acid Derivatives Deck (27)
1

Amides

the condensation produce of carboxylic acids and ammonia or amines

2

Amides suffix

-amide

3

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

N-

4

Cyclic amides are called

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

5

Esters

condensation products of carboxylic acids with alcohols (fisher esterification)

6

Ester suffix

-oate

7

Cyclic esters

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

8

Tracylglycerols

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

9

Saponification

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

10

Anhydrides

condensation dimers of carboxylic acids

11

Symmetric anhydrides are named for:

the parent carboxylic acid, followed by anhydride

12

Asymmetric anhydrides are named:

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

13

How can cyclic anhydrides be synthesized?

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

14

In nucleophilic substitution reactions, which is most reactive?

Anhydride, amides, esters

Anhydride, esters, amides

15

Steric hindrance

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

16

Protecting groups

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

17

Induction

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.

18

Conjugation

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

19

Resonance

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

20

Increased strain can

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

21

Ring strain

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

22

How can anhydrides be cleaved?

an addition of a nucleophile.

23

Anhydride + ammonia or amine

results in an amide and a carboxylic acid

24

Anhydride + alcohol

ester and a carboxylic acid

25

Anhydride + water

2 carboxylic acids

26

Transesterification

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

27

Amides can be hydrolyzed to carboxylic acids under

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