Question
Chemistry Question on Reaction Mechanisms & Synthesis
Identify the major product in the following reaction.
Solution
This is an elimination reaction (E2 mechanism) where the hydroxide ion acts as a strong base. The steps of the reaction are as follows:
Step 1: Identify the base and leaving group
In the presence of OH− and EtOH, the bromine atom (Br) acts as the leaving group. The hydroxide ion abstracts a proton (H+) from the adjacent carbon atom, resulting in the formation of a double bond.
Step 2: Formation of the double bond
Since the reaction proceeds via the E2 mechanism, the elimination occurs in a single step. The base removes a β-hydrogen atom (attached to the carbon next to the carbon with Br), and the Br− leaves, resulting in the formation of a double bond between the α- and β-carbons.
Step 3: Determine the major product
The double bond forms between the α-carbon (the one originally bonded to the bromine atom) and the β-carbon. Due to Zaitsev's rule, the most substituted alkene is the major product. Hence, the major product is cyclopentene with a methyl (CH3) substituent.
Final Answer: (3) Cyclopentene with a CH3 substituent.