Question

10 mol%\nAr\nHN\nAr\nOTMS\ntoluene, RT, 4\AA MS\n10 mol% PhCO?H\nS\nPh\n85% yield\nH\nPh\n+\nHS\nH

          10 mol%\nAr\nHN\nAr\nOTMS\ntoluene, RT, 4\AA MS\n10 mol% PhCO?H\nS\nPh\n85% yield\nH\nPh\n+\nHS\nH

$10 mol%\nAr\nHN\nAr\nOTMS\ntoluene, RT, 4\AA MS\n10 mol% PhCO?H\nS\nPh\n85% yield\nH\nPh\n+\nHS\nH$

Added by Mark H.

Chemistry: Structure and Properties

Nivaldo Tro 2nd Edition

Instant Answer

Solved by Expert Madhur L

07/04/2023

Step 1

Step 1: The organocatalyst, in this case, OTMS, activates the carbonyl group of PhCOH through hydrogen bonding with the NH group. Show more…

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Please give a reasonable mechanism for the following reaction using organocatalysis. Please draw it out and write out the steps. PLEASE SHOW WITH ARROWS. 10 mol% OTMS NH toluene, RT. 4A MS 10 mol % PhCOH SH Ph 85% yield

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Question

10 mol%\nAr\nHN\nAr\nOTMS\ntoluene, RT, 4\AA MS\n10 mol% PhCO?H\nS\nPh\n85% yield\nH\nPh\n+\nHS\nH

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