Amines

Identify B formed in the reaction. Cl-(CH2)4-Cl excess NH3 A NaOH B + H2O + NaCl

1. [figure]
2. [figure]
3. -Cl +NH3-(CH2)4- +NH3Cl-
4. H2N-(CH2)4-NH2

Answer

(4) H2N-(CH2)4-NH2

Solution

Ammonolysis: excess NH3 replaces both Cl; the HCl formed converts each -NH2 into - +NH3Cl-:

Cl-(CH2)4-Cl + 2NH3 -Cl +NH3-(CH2)4- +NH3Cl- (A)

A + 2NaOH H2N-(CH2)4-NH2 + 2H2O + 2NaCl

∴ B = H2N-(CH2)4-NH2

∵ NaOH (stronger base) frees the amine from its ammonium salt.

Answer: (4)