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Basics of Organic Chemistry question

2017 · 9 Apr · Shift 1 · Q6
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Basics of Organic Chemistry question

2017 · 9 Apr · Shift 1 · Q6

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
In the following structure, the double bonds are marked as I, II, III and IV JEE Main 2017 (Online) 9th April Morning Slot Chemistry - Basics of Organic Chemistry Question 216 English Geometrical isomerism is not possible at site (s) :
  1. A
    III
  2. B
    I
  3. C
    I and III
  4. D
    III and IV
View written solutionFree

Correct answer: B

  1. Condition for geometrical isomerism around a double bond
    Geometrical isomerism (cisciscis-transtranstrans / EEE-ZZZ) is possible only when each carbon atom of the C=CC=CC=C bond carries two different substituents.

    If on either carbon of the double bond, the two attached groups are identical, then geometrical isomerism is not possible.

  2. Check each marked double bond
    Since the structure has four marked double bonds I,II,III,I, II, III,I,II,III, and IVIVIV, we inspect each one using the above rule.

  3. Site III
    At double bond III, one of the double-bonded carbons has two identical substituents, so the required condition for geometrical isomerism fails.
    Therefore, geometrical isomerism is not possible at site III.

  4. Sites II,III,II, III,II,III, and IVIVIV
    For each of these double bonds, both carbons of the C=CC=CC=C have two different groups attached. Hence they satisfy the condition for geometrical isomerism.
    Therefore, geometrical isomerism is possible at II,III,II, III,II,III, and IVIVIV.

  5. Conclusion
    The only site where geometrical isomerism is not possible is: III

  6. Match with options
    Option B: III is correct.

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