Thestereoisomer whichreacts faster in the elimination reaction on treatment with sodium ethoxide in ethanol is to be predicted. Concept Introduction: > Dehydrohalogenation reaction is the loss of hydrogen and a halogen from adjacent carbon atoms in an alkyl halide to form the most stable alkene by β eliminations. > E 2 elimination reactions are favored whenever an alkyl halide is treated with a strong base. > The difference in the reaction rates between the two stereoisomers results from different degrees of π bond development in the E 2 transition state. > The anti-coplanar arrangement imposes little strain in the E 2 transition state, and elimination occurs readily. An absence of anti-coplanar arrangement increases the strain in the E 2 transition state, and this slows the rate of elimination.

Question

3) The following molecule, chloral is a common precursor to chloral hydrate, an acetal type molecule that was a first-generation anesthetic. Draw a mechanism that accounts for tis formation and speculate why it does not require the use of an acid catalyst, like most hemiacetal and acetal reaction: (10 pts) H H₂O

Answer 1

Question

Chapter 7.16, Problem 26P

Interpretation Introduction

Interpretation:

Thestereoisomer whichreacts faster in the elimination reaction on treatment with sodium ethoxide in ethanol is to be predicted.

Concept Introduction:
>
Dehydrohalogenation reaction is the loss of hydrogen and a halogen from adjacent carbon atoms in an alkyl halide to form the most stable alkene by β eliminations.
>
E2 elimination reactions are favored whenever an alkyl halide is treated with a strong base.
>
The difference in the reaction rates between the two stereoisomers results from different degrees of π bond development in the E2 transition state.
>
The anti-coplanar arrangement imposes little strain in the E2 transition state, and elimination occurs readily. An absence of anti-coplanar arrangement increases the strain in the E2 transition state, and this slows the rate of elimination.

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3) The following molecule, chloral is a common precursor to chloral hydrate, an acetal type molecule that was a first-generation anesthetic. Draw a mechanism that accounts for tis formation and speculate why it does not require the use of an acid catalyst, like most hemiacetal and acetal reaction: (10 pts) H H₂O

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