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Ch.3 - Structure and Stereochemistry of Alkanes
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh.3 - Structure and Stereochemistry of Alkanes문제 30c
3장, 문제 30c

Draw the most stable conformation of
c. trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.

검증된 단계별 안내
1
Begin by understanding the structure of cyclohexane. Cyclohexane can adopt several conformations, but the chair conformation is the most stable due to minimized steric strain and torsional strain.
Identify the substituents on the cyclohexane ring. In this case, we have a tert-butyl group and a 1,1-dimethylpropyl group. The tert-butyl group is bulky and prefers to be in an equatorial position to minimize steric hindrance.
Since the compound is trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane, place the tert-butyl group on one carbon in the equatorial position. Then, place the 1,1-dimethylpropyl group on the third carbon in the opposite equatorial position to maintain the trans configuration.
Ensure that the cyclohexane ring is in the chair conformation. This conformation allows both bulky groups to be equatorial, which is the most stable arrangement due to reduced steric interactions.
Double-check the placement of the substituents to confirm that they are trans to each other, meaning they are on opposite sides of the cyclohexane ring. This ensures the correct stereochemistry for the trans configuration.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
6m

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Cyclohexane Conformations

Cyclohexane can adopt several conformations, with the chair conformation being the most stable due to minimized steric strain and torsional strain. Understanding the chair conformation is crucial for determining the most stable arrangement of substituents on the cyclohexane ring.
추천 영상:
03:29
Understanding what a conformer is.

Axial and Equatorial Positions

In the chair conformation of cyclohexane, substituents can occupy axial or equatorial positions. Equatorial positions are generally more stable for bulky groups due to reduced steric hindrance, which is essential for determining the most stable conformation of substituted cyclohexanes.
추천 영상:
04:02
Equatorial Preference

Trans Configuration

The trans configuration refers to substituents being on opposite sides of the cyclohexane ring. This affects the placement of groups in axial or equatorial positions, influencing the stability of the conformation. Recognizing trans configuration helps in correctly positioning substituents in the most stable conformation.
추천 영상:
02:14
The Electron Configuration
관련 실천
교과서 질문

Name the following compounds.

(c)

(d)

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교과서 질문

Use your models to do a chair–chair interconversion on each ring of the conformation of cis-decalin shown in Figure 3-27. Draw the conformation that results.

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교과서 질문

Draw the most stable conformation of

b. trans-1-tert-butyl-2-methylcyclohexane.

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교과서 질문

Draw the most stable conformation of

a. cis-1-tert-butyl-3-ethylcyclohexane.

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교과서 질문

Draw the two chair conformations of each of the following substituted cyclohexanes. In each case, label the more stable conformation.]

c. cis-1-ethyl-4-isopropylcyclohexane

d. trans-1-ethyl-4-methylcyclohexane

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교과서 질문

Name the following compounds.

(a)

(b)

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