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Chapter 11: Q.52E (page 350)

Question: Predict the major alkene product of the following E1 reaction:

Short Answer

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Answer

Step by step solution

01

E1 reaction

E1 reaction is a substitution nucleophilic unimolecular reaction. It follows first-order kinetics with respect to the substrate.

In the E1 reaction, the deprotonation of hydrogen occurs leading to the formation of carbocation which forms the alkene.

02

Formation of product

In the E1 reaction the deprotonation of hydrogen occur lead to the formation of carbocation which forms the alkene by the removal of the halide (Br) as shown as one of the major product:

Formation of Major Product

It also leads to the formation of minor products like:

Possible Products

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Most popular questions from this chapter

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.

One step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.

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:What products would you expect from the reaction of 1-bromopropane with each of the following?

(b) KOC(CH3)

Among the many examples of reactions that occur with incomplete racemization, the optically pure tosylate of 2,2-dimethyl-1-phenyl-1-propan([α]D= 230.3) gives the corresponding acetate ([α]D= 15.3) when heated inacetic acid. If complete inversion had occurred, the optically pure acetatewould have had[α]D= 153.6. What percentage racemization and what percentageinversion occurred in this reaction?
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