The chemistry of derivatives of trans-decalin is of interest because this ring system is part of the structure of steroids. Make models of the brominated systems (i and ii) to help you answer the following questions.

(a) One of the molecules undergoes E2 reaction with NaOCH2CH3 in CH3CH2OH considerably faster than does the other. Which molecule is which? Explain
(b) The following deuterated analogs of systems i and ii react with base to give the products shown.

Specify whether anti or syn eliminations have taken place. Draw the conformations that the molecules must adopt for elimination to occur. Does your answer to (b) help you in solving (a)?

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CH H3 CH, CH Br CH: CH NaOCH,CH.. CHỊCH-OH All D retained) CH3 i-deuterated CH3 CH NaOCH CH,, CH,CH OH (All D lost) CH3 CH ii-deuterated