Show how a mixture of n-butylamines prepared from n-butyl bromide and an excess of n-butylamine might be resolved into its components by reaction with succinic anhydride, separation of the products through advantage of their solubility properties in acid or base, and regeneration of the corresponding amines. Write equations for the reactions involved.

A mixture of n-butylamines prepared from n-butyl bromide and an excess of n-butylamine can be resolved into components by reacting with succinic anhydride to give N-(n-butyl)-n-butylsuccinamic acid. The products can then be separated by exploiting their solubility properties in acidic and basic solutions. The N-(n-butyl)-n-butylsuccinamic acid can be regenerated back to secondary amine, and the butylammonium bromide can be regenerated back to n-butylamine via their reactions with a base. The overall process involves the following reactions: 1. \(C_4H_9Br + 2 C_4H_9NH_2 \rightarrow C_4H_9NH_2C_4H_9Br + C_4H_9NH_3Br\) 2. \(C_4H_9NH_2C_4H_9Br + (CH_2CO)_2O \rightarrow C_4H_9NH(C_4H_9Br)(CH_2COOH) + CH_3COOH\) 3. \(C_4H_9NH(C_4H_9Br)(CH_2COOH)_{(s)} + H^+_{(aq)} \rightarrow C_4H_9NH(C_4H_9Br)(CH_2COOH)H^+_{(s)}\) 4. \(C_4H_9NH(C_4H_9Br)(CH_2COOH)H^+_{(s)} + OH^-_{(aq)} \rightarrow C_4H_9NH(C_4H_9Br)(CH_2COO^-)_{(aq)} + H_2O_{(l)}\) 5. \(C_4H_9NH(C_4H_9Br)(CH_2COOH) + KOH \rightarrow C_4H_9NH_2C_4H_9Br + KCH_2COO\) 6. \(C_4H_9NH_3Br + KOH \rightarrow C_4H_9NH_2 + KBr + H_2O\)