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Chapter 11: Q 11-11-41 E-c (page 350)

Which compound in each of the following pairs will react faster in an SN2reaction with OH-?

(c)(CH3)3CClorCH3Cl

Short Answer

Expert verified

CH3Cl

Step by step solution

01

SN2 reaction

It is a nucleophilic substitution reaction in which an old bond is broken, and new bond is formed. Both processes co-occur. Hence, it’s a single-step reaction.

The two reacting species are involved in the rate determining steps.

02

Nucleophile

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons ready for bonding.

03

Species react faster with OH-

If the species is a better leaving group, then it reacts faster with the nucleophile.

Cl is a better leaving group but (CH3)3 is a very bulky group, so it cannot show nucleophilic substitution easily compared to CH3which a lighter group and the best is leaving group.

CH3Cl show fast reaction than(CH3)3Cl

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Most popular questions from this chapter

Question: What stereochemistry do you expect for the alkene obtained by E2 elimination of (1R, 2R)-1,2-dibromo-1,2-diphenylethane? Draw a Newman projection of the reacting conformation.

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane:

(c)CH3S-

Which substance in each of the following pairs is more reactive as a nucleophile? Explain.

(a)CH32N-orCH32NH(b) (CH3)3Bor(CH3)3N(c)H2OorH2S

Methyl esters (RCO2CH3) undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI in dimethylformamide:

The following evidence has been obtained: (1) The reaction occurs much faster in DMF than in ethanol. (2) The corresponding ethyl ester (RCO2CH2CH3) cleaves approximately 10 times more slowly than the methyl ester. Propose a mechanism for the reaction. What other kinds of experimental evidence could you gather to support your hypothesis?

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane:

a) CN-
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