Answered: My question is- Using IR, how can the…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 23E

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Reduction of 4-tert-butylcyclohexanone
Introduction
One of the last topics covered in Organic I was the reduction of carbonyl containing compounds such as
aldehydes, ketones, esters, and carboxylic acids. Reduction can be defined in many different ways: one
of which is the increase in hydrogen atoms in the compound. One of the most important reactions for
synthesizing primary and secondary alcohols is through the reduction of aldehydes and ketones by
adding H2 across carbonyl double bond. One of the most common methods to achieve this
transformation is through a metal hydride delivery agent such as lithium aluminum hydride (LAH) or
sodium borohydride (NaBH4).
The first step in this reaction is the transfer of a hydride ion to the carbon of the carbonyl. The hydride
acts as a nucleophile and attacks the carbon of the carbonyl. The hydride can either come in via an
axial attack or an equatorial attack depending on steric factors and the placement of other substituents
on the ring. Below is the reaction scheme. Take note that some arrows are missing so be sure to
include those when writing the mechanism in your prelab report. Typically, the axial attack is preferred
over the equatorial attack, leading to the alcohol in the equatorial position. This type of reaction is
stereoselective since one stereoisomer is preferred over another. For the reaction in this week’s
experiment, a mixture of diasteriomeric alcohols will be produced and analyzed.

If a more sterically hindered reducing agent is used, then the opposite product ratio is observed. If they
were to make an axial attack, these hydride reagents would sterically clash with 1,3-diaxial hydrogen
atoms.

My question is-

Using IR, how can the product formation be confirmed? List specific peaks along with their
associated stretch or bend that can be used to identify the product from the reactant.

Experiment - Reduction of t-butylcyclohexanone ធ
A
Q ↑↓
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The first step in this reaction is the transfer of a hydride ion to the carbon of the carbonyl. The hydride
acts as a nucleophile and attacks the carbon of the carbonyl. The hydride can either come in via an
axial attack or an equatorial attack depending on steric factors and the placement of other substituents
on the ring. Below is the reaction scheme. Take note that some arrows are missing so be sure to
include those when writing the mechanism in your prelab report. Typically, the axial attack is preferred
over the equatorial attack, leading to the alcohol in the equatorial position. This type of reaction is
stereoselective since one stereoisomer is preferred over another. For the reaction in this week's
experiment, a mixture of diasteriomeric alcohols will be produced and analyzed.
1 of 4
(H3C)3C-
ملے اور میں
Figure 1
axial attack
equatorial attack
(H3C)3C-
(H3C)3C-
H
H
H
HⓇ
(H3C)3C-
(H3C)3C-
90% trans
10% cis
H
OH
OH
H
If a more sterically hindered reducing agent is used, then the opposite product ratio is observed. If they
were to make an axial attack, these hydride reagents would sterically clash with 1,3-diaxial hydrogen
atoms.

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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