Learning Path
Question & Answer1
Understand Question2
Review Options3
Learn Explanation4
Explore TopicChoose the Best Answer
A
Axial substituents increase steric strain when flipped to the equatorial position.
B
Equatorial substituents experience greater torsional strain after a ring flip.
C
Both axial and equatorial substituents have the same energy in all conformations.
D
Ring flipping has no effect on the stability of the cyclohexane conformations.
Understanding the Answer
Let's break down why this is correct
Answer
Ring flipping swaps the axial and equatorial positions of the methyl groups in 1,2‑dimethylcyclohexane, so each methyl alternates between being higher (axial) and lower (equatorial). In the energy diagram this appears as a crossing of two energy curves, each representing one conformer: the axial‑high, equatorial‑low curve and the reverse. The axial conformation is higher in energy because of steric crowding, while the equatorial conformation is lower. When the ring flips, the energy rises as the methyls climb into axial positions and then falls back when they become equatorial again. For example, the energy of the axial conformation might be 3 kcal/mol above the equatorial one, and the flip moves the system back and forth between these two energy levels.
Detailed Explanation
Axial groups sit above and below the ring and bump into other axial hydrogens a short distance away. Other options are incorrect because Equatorial groups are farther from the ring and do not clash with other bonds; Axial substituents have higher energy because they press against other atoms.
Key Concepts
Ring Flipping
Conformational Energy Diagrams
Topic
Cycloalkane Conformations
Difficulty
medium level question
Cognitive Level
understand
Practice Similar Questions
Test your understanding with related questions
1
Question 1When analyzing a cyclohexane derivative with a bulky substituent in the axial position, what effect does ring flipping have on the stability of the molecule?
mediumChemistry
Practice
2
Question 2In a substituted cyclohexane where a large substituent is present in the equatorial position, what is the likely impact on the molecule's stability when the ring undergoes flipping?
mediumChemistry
Practice
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