Question

An organic compound P (C\(_8\)H\(_16\)) produces a meso compound upon oxidation with OsO\(_4\)/NMO. The compound P is

• A. (E)-4-octene
• B. (Z)-4-octene
• C. (E)-3-octene
• D. (Z)-3-octene

Hint:

The formation of meso compounds occurs when the oxidation of alkenes results in two chiral centers, but the compound retains a plane of symmetry.

Answer 1

The Correct Option is B

Step 1: Understanding the reaction.
OsO\(_4\)/NMO (osmium tetroxide/N-methylmorpholine N-oxide) is used in the oxidation of alkenes to form diols, specifically syn diols, where the hydroxyl groups are added to the same side of the double bond. In this case, the oxidation of a specific alkene results in a meso compound, which is achiral despite having stereocenters.
Step 2: Analyzing the structure of possible P.
- (Z)-4-octene is a compound that, upon oxidation, can lead to a meso compound. The meso compound formed will have a plane of symmetry, which makes it achiral despite having chiral centers.
- The other options would either not result in a meso compound or produce an achiral compound without the correct symmetry.
Step 3: Conclusion.
The correct compound P that produces a meso compound upon oxidation with OsO\(_4\)/NMO is (Z)-4-octene.
Final Answer: \[ \boxed{(Z)-4-octene} \]