Questions tagged [cyclohexane]

Cyclohexane is a cycloalkane with the molecular formula $\ce{C6H12}$. This tag should be applied to questions about the properties and reactions of cyclohexane and its derivatives.

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23
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21k views

Is cis-1,2-dimethylcyclohexane a meso compound?

I was watching a video lecture today on hydrocarbons and came across this. The instructor says that, as there is a plane of symmetry, cis-1,2-dimethylcyclohexane is a meso-compound: However, the ...
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1answer
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Conformations of Cyclohexane

Is there any such thing as a twist chair conformation? Also, the boat and the chair conformations are achiral, while the twist boat conformation of cyclohexane is chiral and dissymetric. What about ...
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3answers
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Why does 1,3-dimethylcyclopent-1-ene have geometric isomerism while 1-bromo-2-chlorobenzene doesn't?

The bottom compound has bromine and an R group connected to one of its SP2 double bond carbons, and chlorine and the same R group connected to the other. This fact, it would seem, indicates cis-trans ...
11
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2answers
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Effect of periodic acid on cyclohexane derivatives

Periodic acid (per-iodic acid, $\ce{HIO4}$ ) cleaves vicinal diols(to carbonyls) via a cyclic intermediate. Due to the cyclic intermediate, it needs a syn configuration for the $\ce{-OH}$ groups for ...
6
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3answers
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E2 Elimination; Anti-periplanar beta hydrogen

I'm confused by this picture I found on masterorganicchemistry.com—a very popular organic chemistry website: I agree that the product is a product. However, can't there be another product? ...
2
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1answer
12k views

Why does 1,2-dimethylcyclohexane only possess three stereoisomers? [duplicate]

Why does 1,2-dimethylcyclohexane in chair form have only three stereoisomers? I understand that the trans isomer doesn't possess plane of symmetry and thus it has two stereoisomers. But my book says ...
4
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1answer
4k views

Is the SN1 reaction faster with an axial or equatorial leaving group?

Why does compound 1 undergo the $\mathrm{S_N1}$ reaction faster than 2 even though both proceed via the same carbocation intermediate?
4
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1answer
211 views

Steric effect of t-butyl group on SN1 on a cyclohexane ring

This is a question from GRB Kota Question Bank Organic Chemistry, Chapter 3, Reasoning type, Q. 4: Assertion: trans-1-t-butyl-4-chlorocyclohexane is less reactive than cis-1-t-butyl-4-...
2
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2answers
159 views

Is it correct to look at plane of symmetry in substituted cyclohexane for determining a meso compound?

I read this question and it's answer by @orthocresol. Now, he has written that the compound in question is meso not because there is a plane of symmetry but because of the rapid flipping of the ...