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Chapter 11: Q11.73E (page 350)

Propose a structure for an alkyl halide that gives only (E)-3-methyl-2-phenyl-2-pentene on E2elimination. Make sure you indicate the stereochemistry.

Short Answer

Expert verified

Formation of the desired product

Step by step solution

01

Zaitsev’s rule

According to Zaitsev鈥檚 rule, base-induced elimination reactions generally give a more stable alkene product鈥攖hat is, the alkene with more alkyl substituents on the double-bond carbons.

02

Structure of alkyl halide

E2-elimination is trans elimination, in which hydrogen and halogen should be in an antiperiplanar position.

The reaction is represented as:

Formation of the desired product

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Most popular questions from this chapter

What product would you expect from a nucleophilic substitution reaction of (S) -2-bromohexane with acetate ion, CH3CO2-? Assume that inversion of configuration occurs, and show the stereochemistry of both the reactant and

product.

Question: 1-Chloro-1,2-diphenylethane can undergo E2 elimination to give either cis- or trans-1,2-diphenylethylene (stilbene). Draw Newman projections of the reactive conformations leading to both possible products, and suggest a reason why the trans alkene is the major product.

Question: Order each of the following sets of compounds with respect to reactivity:

b.

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-
See all solutions

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