JEE Main 2015 · 11 Apr · Shift 1 · Chemistry Q54

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ChemistrySingle correct+4 / -1Question 54 of 90

What is the major product expected from the following reaction ?

1-Methylcyclopentene $\xrightarrow{\text{D}-\text{Cl}}$

Where D is an isotope of Hydrogen.

1-Methylcyclopentene reacting with D-Cl.

Drawn with CH₃ at the top, H and Cl beside the ring bond, D at the bottom

A cyclopentane ring with substituents drawn on two adjacent ring carbons: CH₃ above the upper ring carbon, the labels H (left) and Cl (right) beside the right-hand ring bond, D below the lower ring carbon.

Drawn with CH₃ at the top, D and Cl beside the ring bond, H at the bottom

A cyclopentane ring with substituents drawn on two adjacent ring carbons: CH₃ above, D (left) and Cl (right) beside the right-hand ring bond, H below.

Drawn with D at the top, H and CH₃ beside the ring bond, Cl at the bottom

A cyclopentane ring with substituents drawn on two adjacent ring carbons: D above, H (left) and CH₃ (right) beside the right-hand ring bond, Cl below.

Drawn with D at the top, Cl and CH₃ beside the ring bond, H at the bottom

A cyclopentane ring with substituents drawn on two adjacent ring carbons: D above, Cl (left) and CH₃ (right) beside the right-hand ring bond, H below.

Answer and worked solution

Official answer: B

Markovnikov addition: $\ce{D+}$ adds to C2, giving the tertiary carbocation at C1, which takes $\ce{Cl-}$ . The product is 1-chloro-2-deuterio-1-methylcyclopentane: Cl and CH₃ on C1, D and H on C2. The key gives structure (2).

Topics:Alkenes Reactive intermediates

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JEE Main 2015 · 11 Apr · Shift 1, Chemistry question 54