Draw the organic product of the following reaction: CH3 meta-Chloroperoxybenzoic acid CH3-C(CH3)-CH2-CH3 You do not have to consider stereochemistry. Indicate regiochemistry when relevant. The aromatic ring, when present, is unreactive in all cases. Do not draw organic or inorganic by-products.
The Correct Answer and Explanation is:
This reaction involves a peracid oxidation reaction with a compound containing a chloro group (meta-Chloroperoxybenzoic acid) and an alkene group (CH3-C(CH3)-CH2-CH3). The reaction is likely to be a typical electrophilic addition of the peracid to the double bond, producing a new product.
Step-by-step explanation:
- Chloroperoxybenzoic acid (m-CPBA): This is a peracid, which is known to react with alkenes, resulting in the formation of an epoxide (three-membered oxygen ring).
- Alkene Reaction: The alkene (CH3-C(CH3)-CH2-CH3), when treated with m-CPBA, undergoes an electrophilic addition reaction. The peracid acts as an electrophile, attacking the double bond of the alkene.
- Regiochemistry: Since the aromatic ring is unreactive (as stated in the problem), the reaction happens only at the alkene site. The addition of the oxygen atom from the peracid will result in the formation of an epoxide group across the alkene. The regiochemistry of the addition is controlled by the steric and electronic effects of the substituents attached to the carbon chain. In this case, the methyl group (CH3) attached to the carbon next to the double bond will direct the addition to favor the formation of a more stable, substituted epoxide ring.
- Product: The final product will be a bicyclic structure known as an epoxide, with the oxygen from the peracid attached to the carbon-carbon double bond. The structure would look like this: CH3-CH(CH3)-CH2-O-CH3.
This reaction is a classic example of an electrophilic addition of peracid to an alkene, forming an epoxide. The reaction is regioselective, and because of the bulky groups, the addition happens to give the more stable epoxide product. No other products are formed, and there are no organic by-products as per the instructions.
