T3.2 Reactions Spivak

Question 1

Alkyl Halide –> Quaternary Ammonium Salt

Answer 1

NR3

Heat

Question 2

Alkyl Halide –> Primary Amine

Gabriel

Answer 2

Pthalamide anion (deprot w/ OH-)
Alkyl Halide
Acid / Water

Question 3

Nitrile –> Primary Amine

Answer 3

2 LiAlH4

2 H2O

Question 4

Primary Imine –> Primary Amines

Answer 4

BH3CN
H2O

OR

Pd/C
H2

Question 5

Secondary Imine –> Secondary Amine

Answer 5

Same as Primary

BH3CN / H2O

Pd/C H2

Question 6

Aldehyde/Ketone –> Imine(2°)

Answer 6

HCl

1° Amine

Question 7

Aldehyde/Ketone –> Imine (1°)

Answer 7

HCl
Ammonia
Remove Water

Question 8

Aldehyde/Ketone –> Enamine

Answer 8

HCl

Secondary Amine

Question 9

Imine –> Aldehyde/Ketone + X

X can be Ammonia or amine, depending on reaction

Answer 9

HCl

REMOVE H2O

Question 10

Nitrile –> Imine

Answer 10

DIBAL (Diisobutylaluminumhydride)
OH-
H2O

Question 11

Nitrile –> Imine

Answer 11

Grignard

Water work up

Question 12

Imine –> Reduced Amine

Answer 12

Grignard

Water work up

Question 13

Nitrile –> Imine –> Amine

Answer 13

Grignard and water

BH3CN and water

Question 14

Nitrile –> Aldehyde

Answer 14

DIBAL
-OH
H2O
HCl

Question 15

Nitrile –> Ketone

Answer 15

Grignard and water
2HCl
H2O

Question 16

Quat Ammonium Salts –> Alkene

Hoffman elim

Answer 16

-OH

OR

CH3I
Ag2O
Heat

Question 17

Alkyl Halide –> Amine

Answer 17

NH3 for Primary
NRH2 for Secondary
NR2H for Tertiary