Mechanisms reagents and solvents

Question 1

Ketone to cyanohydrin R&S

Answer 1

R = NaCN, H2SO4
S = water

Question 2

Cyanohydrin to ketone R&S

Answer 2

R = NaOH acid catalyst
S = H2O

Question 3

Ketone to secondary alcohol R&S

Answer 3

R = NaBH4
S = EtOH

Question 4

Ketone to tertiary alcohol R&S

Answer 4

R = MeMgBr/ LiMe, H2O step 2 only
S = Et2O/ THF (aprotic)

Question 5

ketone to hydrate R&S

Answer 5

R = H2O
S = H2O

Question 6

Ketone to hemiacetal R&S (acidic and basic)

Answer 6

R = MeOH ( with either HCl/ NaOH)
S = MeOH

Question 7

Hemiacetal to ketone R&S (acidic and basic)

Answer 7

R = H2O (with either HCl or NaOH)
S = H2O

Question 8

Bisulfide addition of a ketone R&S

Answer 8

R = NaHSO3 (sodium bisulfite)
S = H2O

Question 9

Hemiacetal to acetal R&S

Answer 9

R = MeOH (HCl catalyst needed to protonate leaving group)
S = THF

Question 10

Acetal to ketone R&S

Answer 10

R = H2O (HCl catalyst)
S = THF

Question 11

Acid chloride to ester R&S

Answer 11

R = EtOH and base eg pyridine
S = THF

Question 12

Ester to carboxylic acid R&S (acidic and basic)

Answer 12

R = H2O (HCl or NaOH catalyst)
S = H2O

Question 13

Acid chloride to acid anhydride R&S

Answer 13

R = sodium ethanoate
S = THF

Question 14

Acid chloride to amide R&S

Answer 14

R = NH3
S = H2O

Question 15

Amide to carboxylic acid R&S (acidic or basic)

Answer 15

R = H2O, Heat (HCl/NaOH cat )
S = H2O

Question 16

Amide to amine R&S

Answer 16

R = LiAlH4
S = Et2O/ THF (aprotic)

Question 17

Carboxylic acid to acid chloride R&S (two possible reactions)

Answer 17

R = SOCl2
S = none
or
R = PCl5
S = THF

Question 18

Amide to ketone R&S

Answer 18

R = MeMgBr (H2O step 2 & HCl)
S = Et2O/THF

Question 19

Nitrile to ketone R&S

Answer 19

R = RMgBr acid catalyst
S = Et2O/THF

Question 20

Ketone to imine R&S

Answer 20

R = NH3 (HCl catalyst)
S = THF

Question 21

Ketone to alkene R&S

Answer 21

R = phosphonium ylide
S = Et2O (aprotic)

Question 22

Ketone to enol R&S

Answer 22

R = H2O (acid/ base catalyst)

Question 23

ketone to alkyl bromide R&S

Answer 23

R = Br2 and acetic acid AcOH

Question 24

Ketone to ketone with R group added R&S

Answer 24

step one
R = LDA
S = THF
step 2
R = R-I

Question 25

Aldehyde to aldol R&S

Answer 25

R = NaOH
S = H2O