Steroid Reaction Mechanisms by D. N. Kirk, M. P. Hartshorn

By D. N. Kirk, M. P. Hartshorn

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Just as there is an equal probability of finding grapes on either side of the stem in a cluster of grapes, there is an equal probability of finding the Rand S enantiomers in a racemic mixture. SN1 reactions are therefore said to proceed with racemization. If we start with a pure sample of (R)2-bromobutane, for example, we expect the product of the SN 1 reaction with the OH- ion to be a racemic mixture of the two enantiomers of 2-butanol. We are now ready to address a pair of important questions.

N-2- · · ~ H"'---";H )== S RCOOH DCC, DMAP 0 • R)lO tJ Barton ester Na~ S AIBN • R-H S 0Q ) 1 R)lO,-N • RCOCI Bu3SnH Barton ester S t-Bu SH - - - - - - . R-H hv or d An alternative possibility is the introduction of a substituent by reaction with a suitable radical trapping agent: s-n QI CI O==(o.

CH30H~ H (I CH3 I.. CH 2- , CH 3 _ CH 3 I .. - CH 3 Substitution Versus Elimination Reactions There are three ways of pushing the reaction between an alkyl halide and a nuc1eophile toward elimination instead of substitution. • Start with a highly substituted substrate, which is more likely to undergo elimination. Only 10% of a primary alkyl bromide undergoes elimination to form an alkene, for example, when it reacts with an alkoxide Organic Reaction Mechanism 24 ion dissolved in alcohol. The vast majority of the starting material goes on to form the product expected for an SN2 reaction.

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