Step 1: Nucleophilic substitution (\( S_N2 \)) with dimethylamine (\( \text{Me}_2\text{NH} \)): The bromine atom at one of the carbons is replaced by the nucleophile (\( \text{Me}_2\text{N} \)) via an \( S_N2 \) mechanism. This forms an intermediate with a quaternary amine at the adjacent carbon. Step 2: Deprotonation: The positively charged intermediate loses a proton (\(-\text{H}^+\)) to stabilize the structure, forming an alkene. Step 3: Second \( S_N2 \) reaction: The second equivalent of dimethylamine attacks the adjacent carbon-bromine bond, substituting the bromine atom with another \( \text{Me}_2\text{N} \) group. The final product contains two \( \text{Me}_2\text{N} \) groups attached to the cyclopentane ring at adjacent positions. The above mechanism is valid for both cis and trans isomers. Hence, the products are the same for both.
Was this answer helpful?
0
0
Top Questions on Nucleophilic and electrophilic substitution reactions (both aromatic and aliphatic)
