Ch. 22: Amines

Question 1

Alkyl Halide to Amine

Answer 1

1. NaCN, SN2 2. XS LAH 3. H2O

Question 2

Carboxylic Acid to Amine

Answer 2

1. SOCl2 2. XS NH3 3. XS LAH 4. H2O

Question 3

Benzene to Amine

Answer 3

1. HNO3, H2SO4 2. H2, Pt
   or 1. HNO3, H2SO4 2. Fe, Zn, Sn, or SnCl2 3. NaOH

Question 4

Azide Synthesis

Answer 4

1. NaN3 2. H2, Pt
   or 1. NaN3 2. LAH 3. H2O

Question 5

Gabriel Synthesis

Answer 5

1. KOH 2. R-Br 3. H2NNH2 (replaces Br on R group with NH2)

Question 6

Reductive Amination (Ketone to Amine)

Answer 6

1: NH3, [H+], NaBH3CN
2: R-NH2, [H+], NaBH3CN
3: R2-NH, [H+], NaBH3CN

Question 7

Acylation

Answer 7

Cl-Acyl (adds acyl group w/out Cl)

Question 8

Hofmann Elimination

Answer 8

1. XS CH3I 2. Ag2O, H2O, heat (reduces amine to alkene)

Question 9

Nitrous Acid (R-NH2) to Diazonium Salt

Answer 9

NaNO2, HCl

Question 10

Nitrous Acid (R2-NH) to N-nitrosamine

Answer 10

NaNO2, HCl

Question 11

Sandmeyer Reaction

Answer 11

CuX (X replaces NN triple bond)

Question 12

Fluorination (Schiemann) Rxn

Answer 12

HBF4 (F replaces NN triple bond)

Question 13

Aryldiazonium Salt to Alcohol

Answer 13

H2O, heat

Question 14

Aryldiazonium Salt to Hydrogen

Answer 14

H3PO4

Question 15

Where is bond formed in ago coupling?

Answer 15

Triple bond between NN is reduced to double bond and forms new CH3 bond between N and the reagent (opposite side of R group)

Question 16

Nitrogen Heterocycles (2)

Answer 16

• Br2, 0 C (1,2 addition of Br)
• Br2, 300 C (1,3 addition of Br)