Reaction Mechanisms

Question 1

POCl3/pyridine

Answer 1

For secondary alcohols, creates double bond–E2

Question 2

Alcohol plus H2CrO4, CrO3, or Potassium dichromate

Answer 2

Makes ketones or carboxylic acids (do not stop at aldehyde stage)

Question 3

Alcohol plus PCC

Answer 3

Makes aldehydes or ketones

Question 4

Alcohol plus Dess-Martin periodinane

Answer 4

Makes aldehydes or ketones

Question 5

Nucleophile plus carbonyl group

Answer 5

Alcohol

Question 6

Carbonyl plus water in strong acid or strong base

Answer 6

A gem diol–1,1 diol/2,2 diol etc

Question 7

Carbonyl plus alcohol in acid

Answer 7

Yields an acetal (or hemiacetal)

Question 8

Carbonyl plus Grignard reagent

Answer 8

An alcohol and carbon-carbon bond

Question 9

Carbonyl plus LAH or NaBH4

Answer 9

Alcohol

Question 10

Carbonyl plus primary amine

Answer 10

Forms an imine

Question 11

Carbonyl plus secondary amine

Answer 11

Produces an enamine

Question 12

Grignard reagents plus CO2

Answer 12

Carboxylic acid

Question 13

Nucleophilic acyl substitution reaction

Nucleophile plus some derivative of COOH

Answer 13

Carbonyl with R group and nucleophile

Question 14

Alcohol plus strong acid and heat

Answer 14

Creates double bond, behaves as an E1 reaction-major product is the double bond between the most substituted carbons

Question 15

Carboxylic acid plus LAH

Answer 15

Primary alcohol