Class 11 Exam  >  Class 11 Questions  >  A mixture containing all the stereoisomers of... Start Learning for Free
A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?
    Correct answer is '4'. Can you explain this answer?
    Most Upvoted Answer
    A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclop...
    Introduction:
    The reaction of a mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene with O3 followed by Zn-hydrolysis results in the formation of four different isomers of products. This can be explained based on the reaction mechanism and the stereochemistry of the starting material.

    Reaction Mechanism:
    The reaction starts with the ozonolysis of the cyclopentene double bond. Ozone (O3) reacts with the double bond to form an ozonide intermediate. This intermediate then undergoes a reductive workup with Zn-H2O to convert it into the products.

    Stereochemistry of 3, 4, 5-trimethyl cyclopentene:
    3, 4, 5-trimethyl cyclopentene is a chiral molecule with a stereocenter at the 3rd carbon atom. It exists as two enantiomers, designated as R and S, due to the presence of a chiral carbon atom. Each enantiomer can further exhibit cis-trans isomerism based on the relative positions of the methyl groups at the 4th and 5th carbon atoms.

    Explanation:
    When the mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene undergoes ozonolysis, the ozonide intermediate is formed. This intermediate can undergo two different types of cleavage: oxidative cleavage and reductive cleavage.

    1. Oxidative Cleavage:
    In oxidative cleavage, the ozonide intermediate is cleaved to form two carbonyl compounds. This cleavage does not affect the stereochemistry of the starting material, and all the isomers will still be present in the products.

    2. Reductive Cleavage:
    In reductive cleavage, the ozonide intermediate is converted into aldehydes or ketones by the addition of Zn-H2O. This step can lead to changes in the stereochemistry of the starting material.

    Different Isomers of Products:
    The four different isomers of the products can be obtained based on the possible combinations of the stereochemistry of the starting material and the reductive cleavage.

    1. R-R isomer: This isomer is obtained when the R-enantiomer of 3, 4, 5-trimethyl cyclopentene undergoes reductive cleavage. The resulting products will retain the R configuration at the stereocenter.

    2. R-S isomer: This isomer is obtained when the R-enantiomer of 3, 4, 5-trimethyl cyclopentene undergoes reductive cleavage. The resulting products will have the S configuration at the stereocenter.

    3. S-R isomer: This isomer is obtained when the S-enantiomer of 3, 4, 5-trimethyl cyclopentene undergoes reductive cleavage. The resulting products will have the R configuration at the stereocenter.

    4. S-S isomer: This isomer is obtained when the S-enantiomer of 3, 4, 5-trimethyl cyclopentene undergoes reductive cleavage. The resulting products will retain the S configuration at the stereocenter.

    Therefore, the reaction of the mixture containing
    Free Test
    Community Answer
    A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclop...
    4 is correct.
    Attention Class 11 Students!
    To make sure you are not studying endlessly, EduRev has designed Class 11 study material, with Structured Courses, Videos, & Test Series. Plus get personalized analysis, doubt solving and improvement plans to achieve a great score in Class 11.
    Explore Courses for Class 11 exam

    Similar Class 11 Doubts

    Top Courses for Class 11

    A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer?
    Question Description
    A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer? for Class 11 2024 is part of Class 11 preparation. The Question and answers have been prepared according to the Class 11 exam syllabus. Information about A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer? covers all topics & solutions for Class 11 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer?.
    Solutions for A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer? in English & in Hindi are available as part of our courses for Class 11. Download more important topics, notes, lectures and mock test series for Class 11 Exam by signing up for free.
    Here you can find the meaning of A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer? defined & explained in the simplest way possible. Besides giving the explanation of A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer?, a detailed solution for A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer? has been provided alongside types of A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer? theory, EduRev gives you an ample number of questions to practice A mixture containing all the stereoisomers of 3, 4, 5-trimethyl cyclopentene is treated with O3 followed by Zn-hydrolysis, how many different isomers of products would result?Correct answer is '4'. Can you explain this answer? tests, examples and also practice Class 11 tests.
    Explore Courses for Class 11 exam

    Top Courses for Class 11

    Explore Courses
    Signup for Free!
    Signup to see your scores go up within 7 days! Learn & Practice with 1000+ FREE Notes, Videos & Tests.
    10M+ students study on EduRev