Chapter 13 - Carboxylic Acid Derivatives

Question 1

List the acid derivatives in order of increasing reactivity

Answer 1

Carboxylate < amides < COOH or esters < acid anhydride < acid chloride

acid chlorides are the best leaving group

Question 2

How does COOH form from a Grignard reagent?

Answer 2

the Grignard reagent will react with CO2 to form a carboxylate ion, which will get quenched to make COOH

Question 3

Fischer Esterificaton

Answer 3

COOH is treated with an acid to form an ester

Question 4

Saponification

Hydrolysis

Answer 4

An ester is treated with water to make COOH; can be done in acidic and basic conditions

Question 5

Which acid derivatives can be reduced by NaBH4?

Which can ONLY be reduced by LAH?

Answer 5

NaBH4 - acid chlorides and acid anhydries

LAH - esters, amides, and carboxylates

Question 6

Hoffman Rearrangement

Answer 6

an amide is treated with Br2 / NaOH to make an amine with ONE LESS carbon than the starting product (this is due to the carbonyl carbon being removed)

Question 7

Reduction can be stopped at the aldehyde level if the starting compound is ______. The reagent used to achieve this is called _____

Answer 7

ester, DIBAL

Question 8

In order to reduce and stop at the aldehyde level using LTBA, the starting compound must be a ____

Answer 8

acid chloride