Amines Rxns

Question 1

Gabriel reaction?

Answer 1

1. 6 ring/5ring system w 2O and NH
2. OH is added
3. H is ripped from ring system
4. Alkyl halide is added- R group is substituted onto ring
5. H+ and H20 is added and ring is split into 6 ring w 2COOH groups
6. In the same step, a (+) primary aliphatic amine is produced from the N-R group that was in the ring
7. OH added
8. RNH3+ -> RNH2

Question 2

Amine w strong acid

Answer 2

Forms a salt (eg. With HCl) which are soluble, stable drugs

Question 3

Amine + alkyl halide

Answer 3

1. Amine acts as a nucleophile
2. The R group from the R-X species is substituted onto the amine
3. -H+
4. This process can continue with more R-X added until NR4+ is achieved

Question 4

Reduction of nitro compounds

Answer 4

1. Nitrocompound (eg. Nitrobenzene) + 3H2 with a Ni catalyst at 3atm
2. = amine subtitled for nitro group plus 2H20

Question 5

Synthesis of phenol via diazonium salt

Answer 5

1. A diazonium salt is a benzene ring-N+—N-Cl-
2. Diazonium salt is formed from aniline reacting with NaNO2 + HCl with H20 at 0 degrees
3. Salt + H20 and heat = phenol + N2

Question 6

Diazonium salt + H3PO2

Answer 6

Benzene

Question 7

Diazonium salt + CuCN= y, y + H20, H+ = x

Answer 7

1. Benzene-CN
2. • H20, H+
     3 = benzoic acid

Question 8

Reduction of amides

Answer 8

1. Amide w/ LiAlH4 + dilute HCl = aliphatic amide (CONH2 -> CNH2)

Question 9

Reduction amination/alkylation (imine)

Answer 9

1. Start with a ketone
2. React w R-NH2 and then NaBH4
3. =Secondary amine