The choice of the leaving group on C2 of the propyl chain in the given transformation and how the transformation can be carried out is to be determined. Concept introduction: In an elimination reaction, the leaving group and a proton are eliminated, usually from adjacent carbons to produce a double bond between the two carbons. If more than one adjacent carbons have protons present on them, the major product of elimination is determined by the conditions under which the reaction is carried out. In general, the most stable, i.e., the most substituted alkene is formed preferentially. This is called the Zaitsev product. The less substituted Hofmann product is formed when the leaving group is bulky and the proton on the less substituted adjacent carbon is in an anti position to the leaving group rather than the proton on the more substituted adjacent carbon. An E1 reaction involves the formation of a carbocation in the first, rate-determining step. A carbocation may be subject to rearrangement, and therefore, can lead to the formation of a mixture of stereoisomers.

Question

Want to see the full answer?

Answer 1

Question

Chapter 13, Problem 13.11P

Interpretation Introduction

Interpretation:

The choice of the leaving group on C2 of the propyl chain in the given transformation and how the transformation can be carried out is to be determined.

Concept introduction:

In an elimination reaction, the leaving group and a proton are eliminated, usually from adjacent carbons to produce a double bond between the two carbons. If more than one adjacent carbons have protons present on them, the major product of elimination is determined by the conditions under which the reaction is carried out. In general, the most stable, i.e., the most substituted alkene is formed preferentially. This is called the Zaitsev product. The less substituted Hofmann product is formed when the leaving group is bulky and the proton on the less substituted adjacent carbon is in an anti position to the leaving group rather than the proton on the more substituted adjacent carbon.

An E1 reaction involves the formation of a carbocation in the first, rate-determining step. A carbocation may be subject to rearrangement, and therefore, can lead to the formation of a mixture of stereoisomers.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Predict the major organic product(s) of the following reactions. Indicate which of the following mechanisms is in operation: SN1, SN2, E1, or E2.

(c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistry

A mixture of butyl acrylate and 4'-chloropropiophenone has been taken for proton NMR analysis. Based on this proton NMR, determine the relative percentage of each compound in the mixture