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JEE Advanced 2022 Paper 2, Chemistry Section 1 Q8: Stereoisomerism

JEE Advanced2022Paper 2Chemistry Section 1
Q.

The total number of chiral molecules formed from one molecule of P on complete ozonolysis (O, Zn/HO) is ________.

Solution

Complete reductive ozonolysis cleaves every C=C of P. The cleavages occur at six C=C bonds, generating seven fragments along the chain.

Working through the symmetric structure:

From each terminal end one obtains acetaldehyde (CHCHO) — achiral.

The fragments adjacent to the chiral C(OH)(CH) centers become -hydroxy 1,2-diketone fragments. Two of the resulting fragments are simple symmetric diketo compounds (achiral) and two are -hydroxy ketoaldehyde fragments that retain the stereogenic carbon bearing the OH and CH; these are the chiral pieces.

The central fragment from the symmetric middle portion is achiral by internal symmetry.

Counting unique chiral molecules among the products: 2.

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