Chap 2

Question 1

Secondary alcohol with strong oxidants

Answer 1

Ketone

Question 2

Primary alcohol with strong oxidants

Answer 2

Hydrate then carboxylic acid

Question 3

Primary alcohol with Pcc and ch2cl2

Answer 3

Aldehyde

Question 4

Ketone With mcpba

Answer 4

Ester

O on most stable (+ side)

Question 5

Carboxylic acid with 1/2 alcohol

Answer 5

Fischer esterification
Ester

3 alcohols don’t work

Reversible

Acidic activation

Question 6

2 carboxylic acids with p2o5, p4o10 in ch2cl2

Answer 6

Anhydride

Same r groups on either side, can be internal

Question 7

Carboxylic acid with Pcl5

Answer 7

Acyl chloride

Question 8

Carboxylic acid with pcl3

Answer 8

Acyl chloride

Question 9

Carboxylic acid with socl2

Answer 9

Acyl chloride

Needs to be anhydrous

Question 10

Can amides be formed from carboxylic acids?

Answer 10

No

Acid base reaction

Question 11

Ester plus water (hydrophobic or hydrophilic)? H2so4 activation

Answer 11

Produces carboxylic acid and alcohol, acidic mechanism

Question 12

Ester plus NaOH (with Etoh and h2o with heat)

Answer 12

Carboxylic acid and alcohol

Basic mechanism (hydrophobic esters)

Question 13

Amide with NaOH (etoh/h20/heat)

Answer 13

Carboxylic acid and ammonia

Irreversible

Basic mechanism

Question 14

Amide with h2o (h2so4/heat)

Answer 14

Carboxylic acid and r group ammonia (r on nh if applicable)

Acidic mechanism

Irreversible

Question 15

R-cN with water (h2so4/heat)

Answer 15

Carboxylic acid (ammonium ion)

Reversible (nitrile hydrolysis)

Question 16

Acyl chloride with carboxylic acid

Answer 16

Anhydride (can be dissymmetrical r groups)

Question 17

Acyl chloride with an alcohol with a Et3N or pyridine

Answer 17

Sacrificial base

Ester formation

Alcohol could react with h that’s why sacrificial base

Works for ALL ROH not just Fischer esterification

Question 18

Acyl chloride plus nh2 or nhr2

Answer 18

Amide

Dry/ch2cl2

Sacrificial base needed

Question 19

Anhydride with carboxylic alcohol

Answer 19

Ester

2 oh group

No need for sacrificial base

Question 20

Ester plus alcohol under acidic conditions

Answer 20

Trans esterification (swap r groups on 0-r side of ester)

Question 21

Reduction of any carboxylic acid derivative is with liah4 thf and h30 workup gives what

Answer 21

Primary alcohol

Question 22

Amide reduction with liah4 and h30+ workup gives what

Answer 22

R-CH2-N-r groups

Question 23

Ester reduction gives what

Answer 23

Alcohol from each side of ester ( 1 primary on c=o side)

Question 24

Acyl reduction gives what

Answer 24

Primary alcohol with cl

Question 25

How to stop at aldehyde stage of reduction

Answer 25

Must use acyl chloride Cool temperature Dry thf Tuned down Version of liah4

Question 26

Ester with organomagnesium or organolitihium with thf and h3o work up

Answer 26

Tertiary alcohol with 2 identical r groups Irreversible

Question 27

To stop at ketone stage with ester reduction by alkylation

Answer 27

option 1 Carboxylic acid with r-Li Option 2 Acyl chloride with organocuperate (-78 degrees) thf Option 3 Nitrile with organo magnesium

Question 28

Co2 In default Organometallic in excess

Answer 28

3 alcohol with 3 identical r groups | Following acidic works up

Question 29

Organometallic in default | Excess co2

Answer 29

Carboxylic acid ( with r group from grignard) then acidic workup