Carboxylic Acid And Derivative Rxns

Question 1

Carboxylic acid-> (SOCL2 and pyr)

Answer 1

Acid chloride
- acid mech
- also works with alcohol but undergoes inversion if chiral

Question 2

Carboxylic acid -> (base and X-R)

Answer 2

Ester (replace H from acid with R)
- basic mech

Question 3

Carboxylic acid -> (R-OH (xs) and acid)

Answer 3

Ester (replace OH with OR)
- acidic mech

Question 4

1’ Amide -> (SOCl2 and pyr)

Answer 4

Nitrile
- resonance then acidic mech

Question 5

Acid chloride or anhydride -> (NaBH4 (2 equiv) and ROH)

Answer 5

1’ alcohol
- basic mech

Question 6

Ester -> (1. LAH (2 equiv) 2. Quench)

Answer 6

1’ alcohol
- no mech

Question 7

Amide -> (1. LAH (2 equiv) 2. Quench)

Answer 7

Amine
- replace double O with 2H

Question 8

Nitrile -> (1. LAH (2 equiv) 2. Quench)

Answer 8

1’ amine
- get rid of triple bond, replace N with NH2

Question 9

Acid chloride, anhydride, or ester -> (1. grignard 2. Quench)

Answer 9

3’ alcohol
- gets rid of LG, changes O to OH, and adds 2 grignard c chains

Question 10

Acid chloride or anhydride -> (R2CuLi)

Answer 10

Ketone
- replace LG with R

Question 11

Carbonyl with LG or Nitrile -> (acid and H2O)

Answer 11

Carboxylic acid
- replace LG or N with OH

Question 12

Alpha H connected to C=O -> (irreversible base and R-X)

Answer 12

Replaces H with R
- LDA = less sub
- NaH = more sub

Question 13

Ketone or ald -> (1. Acid, HNR2, -H2O 2. Conjugated C=O 3. Acid, H2O)

Answer 13

Replaces alpha hydrogen with conjugated C=O
- remove conjugation and place in alpha H space

Question 14

Ketone or ald -> (acid, X2, H2O)

Answer 14

Alpha halogenated
- replaced 1H with X (Br, I, Cl)

Question 15

Carboxylic acid -> (PBr3, Br2, H2O (xs))

Answer 15

Replaced alpha H with Br

Question 16

Ketone -> (-OH (xs), X2 (xs), H2O)

Answer 16

Replaces all alpha H with X

Question 17

Aldehyde or ketone -> (ald or ket, -OH, H2O)

Answer 17

Replaces alpha H with second ald or ket (second ald or ket’s double O replaced with OH)

Question 18

aldehyde or ketone -> (ald or ket, -OH, and heat)

Answer 18

Alpha, beta- unsaturated carbonyl
- adds second ald or ket to alpha H space and replaces double O with a pi bond

Question 19

Ester -> (Ester, -OR and quench)

Answer 19

Beta-keto Ester
- Rids second Ester of its OR and places it in the first Esters alpha H space

Question 20

Nitro -> (1.Fe or Zn, HCl, 2. NaOH)

Answer 20

1’ Amine
- keeps R but replaces NO2 with NH2

Question 21

Amide -> (1. LAH (xs), 2. Quench)

Answer 21

Amine

Question 22

Nitrile -> (1. LAH (xs), 2. Quench)

Answer 22

1’ Amine

Question 23

R-X -> (1. -N3, 2. Reducer (H2/cat or 1. LAH, 2. Quench))

Answer 23

1’ Amine
- “R-NH2”
- replaces X with NH2

Question 24

Phthalimide -> (1. Base, 2. R-X, 3. H2NNH2 or acid, H2O, heat)

Answer 24

1’ Amine
- “R-NH2”

Question 25

Aldehyde or Ketone -> (amine, acid, and NaCNBH3)

Answer 25

Amine
- replaced double O with singly bonded amine

Question 26

Amine -> (1. Me-X, 2. Ag2O, H2O, heat)

Answer 26

Hofmann Alkene
- rids of NH2 and makes a less sub alkene instead
- H2O and heat can be replaced with a strong base and heat

Question 27

Beta keto ester -> (1. Base, 2. R-X, 3. Acid and H2O)

Answer 27

Ketone
- draw ketone, place R from R-X into R space of ketone

Question 28

Malonic Ester -> (1. Base, 2. R-X, 3. Acid and H2O)

Answer 28

Carboxylic Acid
- draw Carboxylic acid, place R from R-X where Carboxylic acid R is

Question 29

2 Thiols -> (oxidant)

Answer 29

Disulfide
- reductant to reverse (Zn, HCl)

Question 30

Sulfide -> (ox) ? -> (ox) ?

Answer 30

Sulfoxide (S, 2 methyl, 1 O)
Sulfone (S, 2 methyl, 2 O)
- Ox can be NaIO4 or H2O2, etc

Question 31

R-OH -> (TBSCl or TMSCl and Et3N)

Answer 31

R-O-TBS or R-O-TMS
-replace H with TBS or TMS

Question 32

R-O-Si -> (1. TBAF 2. Quench)

Answer 32

R-O-H
- replace Si with H

Question 33

Cl3CH -> (1.-OH 2.alkene)

Answer 33

Turn double bond into epoxide form with 2 Cls

Question 34

R-SnBu3 -> (R-X, Pd catalyst)

Answer 34

R-R and X-SnBu3

Question 35

R-B -> (R-X, Pd catalyst, and -OR or -OH)

Answer 35

R-R and HO-B

Question 36

R-ZnX -> (R-X, Pd catalyst)

Answer 36

R-R and XZnX

Question 37

Alpha methyl ketone -> (-OH (xs), X2 (xs), H2O, then Quench)

Answer 37

Carboxylic acid