751
Question
A chloro compound (A) on reduction with Zn-Cu couple and alcohol gives the hydrocarbon (B) with five carbon atoms. When A is dissolved in ether and treated with sodium 2,2,5,5- tetramethylhexane is formed. Write the structures of A and B.
Open in App
Solution
Step 1 : To determine the structure of compound (A)Since A, a five carbon atom chloro compound, on reaction with sodium in ether (Wurtz reaction) gives 2,2,5,5-tetramethylhexane, therefore , A must be neopentyl chloride or 1-chloro-2,2-dimethylpropane.
2CH3−CH3|C|CH3−CH2−Cl+2NaDry ether−−−−−−−−−−→(Wurtz reaction)CH3−CH3|C|CH3−CH2−CH2−CH3|C|CH3−CH3+2NaCl1-Chloro-2,2-dimethylpropane (A) 2,2,5,5-Tetramethylhexane
Step 2 : To determine the structure of compound (B). Since A on reduction with Zn−Cu Couple and alcohol gives a hydrocarbon (B), therefore, B must be neopentane or 2,2-dimethylpropane. CH3−CH3|C|CH3−CH2Cl+2[H]Zn−Cucouple−−−−−−−−→+alcoholCH3−CH3|C|CH3−CH3+HCl 1-Chloro-2,2-dimethylpropane (A) 2,2-Dimethylpropane (B)
Thus, A = 1-chloro-2,2-dimethylpropane and B = 2,2-dimethylpropane
Step 1 : To determine the structure of compound (A)
Since A, a five carbon atom chloro compound, on reaction with sodium in ether (Wurtz reaction) gives 2,2,5,5-tetramethylhexane, therefore , A must be neopentyl chloride or 1-chloro-2,2-dimethylpropane.
2CH3−CH3|C|CH3−CH2−Cl+2NaDry ether−−−−−−−−−−→(Wurtz reaction)CH3−CH3|C|CH3−CH2−CH2−CH3|C|CH3−CH3+2NaCl
1-Chloro-2,2-dimethylpropane (A) 2,2,5,5-Tetramethylhexane
Step 2 : To determine the structure of compound (B). Since A on reduction with Zn−Cu Couple and alcohol gives a hydrocarbon (B), therefore, B must be neopentane or 2,2-dimethylpropane.
CH3−CH3|C|CH3−CH2Cl+2[H]Zn−Cucouple−−−−−−−−→+alcoholCH3−CH3|C|CH3−CH3+HCl
1-Chloro-2,2-dimethylpropane (A) 2,2-Dimethylpropane (B)
Thus, A = 1-chloro-2,2-dimethylpropane and B = 2,2-dimethylpropane
Suggest Corrections
0
Similar questions