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I am very confused about the effect deuterium has on substitution/elimination re

ID: 1064711 • Letter: I

Question

I am very confused about the effect deuterium has on substitution/elimination reactions.

2. When secondary bromides A and B are individually treated with an equivalent amount of NaoMe in methanol solvent under identical reaction conditions they both form a mixture of substitution and elimination products at readily measured rates. If the elimination substitution product ratio from bromide A is 50/50, that same ratio of products from bromide B will be OTS OTS a. Smaller b. Larger c. Deuterated materials such as B do not undergo substitution reactions d. Essentially the same e. This issue is irrelevant because neither A nor B would behave rationally under these reaction conditions.

Explanation / Answer

b. smaller---------answer

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Deuterium KIEs are the proportion of the perprotio to the perdeutero rate constants (KIE kH/kD.)

These impacts are basically because of changes in vibrational modes as a response continues from the reactants to the transition-state structure.

An ordinary KIE (>1) is seen as an aftereffect of the releasing of bonds in the move state, which causes an abatement in the distinction of zero point vitality, and is generally characteristic of an E2 system.

An opposite KIE (<1) comes about because of the fixing of bonds in the transition-state structure, bringing on an expansion in zero point vitality, normal for a Sn2 instrument.

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