Q44. In Chapter 7 we will learn all about a class of reactions including the examplepictured below, where a halide leaves to form a carbocation, which is subsequently attackedfrom either side of the trigonal plane to form an alcohol.XBrBrBrinⒸⓇeBriH₂OConsider the stereochemical possibilities for two diastereomeric starting materials picturedbelow:HBrHOOHHolla) Draw an energy diagram showing on the same set of axes the first steps for each of thetwo bromoalkanes starting materials. Which starting material will react faster, and why?b) Draw an energy diagram showing on the same set of axes the two second steps to formeach of the alochols pictured. Which product will be formed in a larger amount, andwhy?

Any haloalkane that consists of an alkane substituted by at least one bromine atom. Energy…

In Chapter 7 we will learn all about a class of reactions including the example pictured below, where a halide leaves to form a carbocation, which is subsequently attacked from either side of the trigonal plane to form an alcohol. X+X÷X 'Br H₂O HBr OH

In Chapter 7 we will learn all about a class of reactions including the example pictured below, where a halide leaves to form a carbocation, which is subsequently attacked from either side of the trigonal plane to form an alcohol. X+X÷X 'Br H₂O HBr OH

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 46CTQ

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Q44.

In Chapter 7 we will learn all about a class of reactions including the example
pictured below, where a halide leaves to form a carbocation, which is subsequently attacked
from either side of the trigonal plane to form an alcohol.
X
Br
Br
Brin
Ⓒ
Ⓡ
e
Bri
H₂O
Consider the stereochemical possibilities for two diastereomeric starting materials pictured
below:
HBr
HO
OH
Holl
a) Draw an energy diagram showing on the same set of axes the first steps for each of the
two bromoalkanes starting materials. Which starting material will react faster, and why?
b) Draw an energy diagram showing on the same set of axes the two second steps to form
each of the alochols pictured. Which product will be formed in a larger amount, and
why?

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