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.

Filter by
Sorted by
Tagged with
0 votes
0 answers
27 views

Why is 1-ethylcyclohexene more stable than ethylidene cyclohexane?

Both compounds yield the same product, ethylcyclohexane, when hydrogenated. However, 1-ethylcyclohexene has lesser heat of hydrogenation than ethylidenecyclohexane, hence more stable. I want to know ...
Anu Vanguri's user avatar
-2 votes
2 answers
65 views

Cyclohexane replacement in Food Chemical Analysis [closed]

We have to use cyclohexane in the laboratory for the chemical analysis of olive oil in the UV spectrometry. But it's highly toxic for respiration. Can anyone suggest a chemical to replace cyclohexane ...
user143756's user avatar
0 votes
0 answers
44 views

Why the C4 in this 1,3,4,5-substituted Cyclohexanes has a R/S configuration?

(1S,3S,4S,5S)-3,5-dimethoxy-1-phenylcyclohexane-1,4-dithiol. ChemDraw21 shows the C4 is S configuration. However I think C4 has two same function groups(C3 and C5 are both S configuration; C2-1-6 and ...
HasturQ's user avatar
  • 49
0 votes
0 answers
151 views

Calculating energy difference between two 1-4 dimethylcyclohexane conformers

The following question was asked in a quiz at my college Draw the most stable and least stable chair conformer for 1,4-dimethylcyclohexane and calculate the energy difference between these two. Given ...
Priyanshu Choubey's user avatar
2 votes
1 answer
139 views

Can we always use the planar representation of cycloalkanes instead of their true conformations to study their stereochemistry and chirality?

When I have drawn stereoisomers of substituted cyclohexanes and checked if they are chiral, I typically represent the ring as a planar hexagon and look for symmetry elements. For example, I would use ...
Akash's user avatar
  • 335
2 votes
0 answers
51 views

Threshold of steric hindrance for the axial position in cyclohexanes

My professor mentioned that isopropyl is able to go into the axial position on the chair conformation of a cyclohexane, while tert-butyl cannot. This made me wonder then, at what point is a ...
chemN00b's user avatar
  • 342
1 vote
1 answer
71 views

Are substituents placed alphabetically in the name of a cycloalkane?

I named this molecule 1,5-diethyl-2-methyl-4-propylcyclohexane. Is this correct? Or should we somehow use the size of the substituents?
TNF's user avatar
  • 39
2 votes
3 answers
3k views

Why is diequatorial trans-1,2-dimethylcyclohexane more stable than diaxial trans-1,2-dimethylcyclohexane?

Consider diequatorial trans-1,2-dimethylcyclohexane and diaxial trans-1,2-dimethylcyclohexane as shown in the figure below [1, p. 178]. In both compounds, the ring is free of angle strain. trans-1,2-...
An_Elephant's user avatar
5 votes
1 answer
905 views

Why 5-member rings prefer being cis-fused?

It always bothers me how whenever I am doing practice problems I never got a proper explanation as to why 5-member rings prefer(thermodynamically) being cis- rather than trans-fused( as opposed to ...
7daiss's user avatar
  • 93
1 vote
1 answer
4k views

Number of stereoisomers of 1,3,5-trimethylcyclohexane

When I searched the stereoisomers of 1,3,5-trimethylcyclohexane, I got four structures given below. I don't get how structures 1 and 2, 3, and 4 are not the same. Could anyone explain?
L lawliet's user avatar
  • 123
5 votes
1 answer
471 views

Ring Flip of glucose

I have recently read about mutarotation of glucose specifically I am familiar with how cyclic structures like substituted cyclo-hexanes exist in an equilibrium of both their chair conformers. The ...
Anmoldeep's user avatar
3 votes
0 answers
91 views

Planarity at the Junction between multiple Rings

My Approach: As cyclohexane should be in the chair form and cyclopentane should be in the envelope form, more the number of five-membered rings more should be its planarity, as envelope form is more ...
Bhanu Kiran's user avatar
0 votes
1 answer
147 views

Can exact bond angles in cycloalkanes be calculated?

I know that bond angles in cycloalkanes are usually different from $\ce{109.5}^{\circ}$ as predicted by the VSEPR theory because of their shape, and a higher deviation will cause a higher ring strain. ...
Lynn Gu's user avatar
  • 527
3 votes
0 answers
71 views

Can acetaldehyde be condensed with methyl vinyl ketone to form 2-Cyclohexen-1-one as per the Robinson annulation

I have seen that cyclohexanone can react with methyl vinyl ketone to form a fused bicyclic cyclohexenone, I am wondering if the same reaction can be used to produce cyclohexenone the single ring ...
Jack's user avatar
  • 39
2 votes
2 answers
749 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 ...
V.G's user avatar
  • 1,251
5 votes
1 answer
393 views

Is cyclohexane‐1,3‐dicarboxylic acid a correct IUPAC name?

I did the numbering by taking all the functional groups in principal chain (scheme A), but my teacher did it differently and proposed the name cyclohexane‐1,3‐dicarboxylic acid (scheme B): The ...
Rider's user avatar
  • 190
1 vote
1 answer
128 views

Why can't cyclohexylbenzene be called benzylcyclohexane? [closed]

The following structure represents the compound cyclohexylbenzene: Why can't the benzene ring be treated as a substituent and the compound be called benzylcyclohexane?
ErrorEliminator's user avatar
0 votes
3 answers
7k views

How to identify cis and trans forms of cyclohexane [closed]

How can identify which one is cis and which one is trans . If I consider it as a planar molecule (though it is not) I understand that if the substituents are in same side it is cis else trans but this ...
Saniya's user avatar
  • 63
8 votes
1 answer
374 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-...
Safdar Faisal's user avatar
1 vote
1 answer
10k views

How many gauche butane interactions are present in cis-1,2-dimethylcyclohexane?

We were asked to find out the number of Gauche-Butane interactions for this compound: I proceeded by drawing the Newman Projection for this chair conformation as follows and marked the Gauche-Butane ...
Sanu_012's user avatar
  • 307
5 votes
1 answer
1k views

Stability of cyclohexane type species

I came across a question where we have to find out the stability of species that are in chair conformations. The species are as follows: Comparing the 'A' values tells me that compound I, III and VI ...
Sanu_012's user avatar
  • 307
1 vote
0 answers
339 views

Optical activity in cyclohexane [duplicate]

In case of checking for the optical activity of cyclohexane or its derivative why we check for POS and COS in its cyclic 6 membered planar eclipsed state but not by its real conformation it forms ...
user avatar
1 vote
1 answer
836 views

Can a substituted cyclohexane progress through SN1?

I have read that when the leaving group substituent is stuck in the equatorial position for some reason (like from a t-butyl group or a trans decalin), SN2 is either very slow or just doesn't happen ...
Jabbamanga's user avatar
2 votes
0 answers
103 views

Strains in conformations of cyclohexane

I know some the basic kind of strains that can exist in molecules namely Torsional strain (Vanderwaals' strain), steric strain and angle strain. Is it possible to associate a particular type of ...
Chem-Learner's user avatar
0 votes
0 answers
115 views

Why bridged bicyclic compound isn't a preferred product over fused bicylic compound in Robinson Annulation reaction?

Why a doubly-fused cyclohexanone is formed instead of bridged cyclohexanone like product which would be more flexible (entropically-favoured)? Also, the OH group not being at the bridgehead carbon ...
Swastik's user avatar
  • 1,272
0 votes
1 answer
133 views

Why was Nobel Prize given to Baeyer for his "faulty" Baeyer's Strain Theory? [closed]

Baeyer Strain Theory said that using the formula $\frac{(109^ \circ 28' - \alpha)}{2}$, where $\alpha$ is the angle between 2 sides of the cycloalkane, the most stable cycloalkane could be found. ...
user avatar
6 votes
1 answer
628 views

Can a boat conformer of cyclohexane be most stable?

It is well-known that the "chair" conformation of cyclohexane is the most stable of its conformers. But is there any cyclohexane derivative where other notable conformers (boat, half-chair) are the ...
Gopai Mukherjee's user avatar
2 votes
2 answers
535 views

Is boat form of cyclohexane non polar?

In chair form of cyclohexane the C-H dipole moments cancel out each other but in boat form i don't think all dipole moments will be cancelled out. Also if boat form is polar then what will we say ...
Sameer Nilkhan's user avatar
2 votes
1 answer
258 views

Heat of hydrogenation of 1,3-substituted cyclohexanes

From these two molecules in question, (C) should be more unstable as it is in a cis-configuration. The t-butyl and methyl groups being on the same side of the ring would exert a larger steric force on ...
Aniruddha Deb's user avatar
2 votes
2 answers
3k views

Is there a gauche interaction between C-3 and C-6 in cyclohexane?

To my understanding, a gauche interaction occurs between two R groups when staggered by 60 degrees in a Newman Projection. When looking down the C-1 to C-2 bond of a cyclohexane, the Newman Projection ...
Ray J's user avatar
  • 21
6 votes
1 answer
179 views

Cyclohexane derivative formation of carambolaflavone using a Lewis acid catalyst

The scheme below summarizes the results from a study into the optimum conditions needed for a key step in the synthesis of the proposed structure of carambolaflavone, a natural product that has ...
J. Deans's user avatar
  • 175
3 votes
0 answers
897 views

Stability of Cycloalkyl Carbocations

What is the order of stability of the cycloalkyl carbocations? I think the stability should increase as we move from cyclopropyl carbocation to cyclohexyl carbocation, since the angle strain is ...
Ankit Kumar Misra's user avatar
3 votes
0 answers
268 views

Chugaev and Selenoxide Elimination giving different products

In class we are going over intramolecular elimination. In this question I will provide two similar reactants that provide a different mixture of products. The chugaev elimination gives a 50/50 ...
Brian M.'s user avatar
2 votes
1 answer
857 views

Stereochemistry of 1,4 disubstituted cyclohexane [closed]

How are these cyclohexanes identical?
user67074's user avatar
  • 105
1 vote
2 answers
5k views

Is cyclohexane saturated or unsaturated?

I have this confusion that cyclohexane is of form $\ce{C_{n}H_{2n}}$ and so it must be an unsaturated compound, but also it does not have a double or triple bond so it must be saturated.
Rigved Sanku's user avatar
3 votes
1 answer
9k views

Most stable chair conformation

I am asked to draw the most stable chair conformation of (1S,2R,4S)-1-chloro-2-methyl-4-(propan-2-yl)cyclohexane 1. After doing so I am a little uncertain which of the conformations is the most ...
J.Se's user avatar
  • 397
2 votes
1 answer
19k 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 ...
user471651's user avatar
-3 votes
3 answers
3k views

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 ...
user73297's user avatar
5 votes
1 answer
2k views

Synthesis of methylenecyclohexane from cyclohexylmethanol

I want to form methylenecyclohexane from cyclohexylmethanol I'm thinking about an $\mathrm{E1cB}$ mechanism since the β-hydrogens will be quite acidic (similar electronegativity to fluorine). ...
xasthor's user avatar
  • 1,622
4 votes
3 answers
3k views

What would this unsaturated cyclic compound be called?

I came across this compound recently, and havent been able to find out what it's name could possibly be: My guess was maybe it's "cyclohexylene cyclohexane", but not quite sure. Can anyone tell me ...
Pritt says Reinstate Monica's user avatar
0 votes
2 answers
3k views

Cyclohexene reduction reaction with hydrogen gas and ethanol [closed]

I have a following reaction (see below). I found the section of reduction and oxidation states in my book but there is nothing about cyclohexenes. I know that the double bond will be reduced in this ...
kakroin's user avatar
1 vote
1 answer
2k views

Help with absolute configuration of a substituted cyclohexane?

How is the absolute configuration decided when it is a cyclohexane and several stereocenters? Up to now we have only worked with simple molecules which are only 1. I believe the stereocenters here are ...
O.kth's user avatar
  • 119
13 votes
2 answers
3k views

Most stable conformational isomer of 3-methoxycyclohexan-1-ol

Among the following, the most stable isomer is? I am aware of the fact that equatorial substituents are more stable than axial substituents but couldn't proceed to apply it here. However the answer ...
Pink's user avatar
  • 2,143
1 vote
1 answer
1k views

How to determine the stereochemistry after elimination of anti-1-bromo-2-methylcyclohexane?

The question is asking for the product and the answer is C. My expected answer was E. Here's how I tried to solve it: Since Br (the leaving group) is at the equatorial position, the structure would '...
Cindy's user avatar
  • 33
2 votes
1 answer
2k views

Best chair configuration for trimethylcyclohexane matching a specific Haworth projection?

Which option best depicts trimethylcyclohexane shown in the Haworth projection below? I thought B because All the methyl groups are equatorial and equatorial groups are more stable. All the methyl ...
K-Feldspar's user avatar
  • 2,853
26 votes
2 answers
31k 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 ...
user avatar
4 votes
1 answer
5k 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?
user avatar
4 votes
1 answer
4k views

Can wedge and dash bonds on 1, 2 position of cyclohexane ring be used to signify trans orientation of the substituents?

I've to make the structural isomers for cyclohexane. On position 1, there's a methane group with wedge bond and on position 2, a methane with dash bond. So I'll have to make the trans isomers only as ...
user31968's user avatar
6 votes
1 answer
455 views

Diastereoselectivity in synthesis problem (4 stereocenters)

Why is the particular diastereomer the major product of the sequence starting from racemic enone? I know that hydroboration is syn, therefore the arrangement of ring junction H atom and OH group. Why ...
EJC's user avatar
  • 14.3k
10 votes
1 answer
2k views

Decarboxylation / Elimination type reaction

I'm quite familiar with E1/E2 reactions and usually use those ideas to explain elimination reactions, however I came across a reaction which was a bit different (in the sense it isn't E1/E2) but still ...
Petrichorr's user avatar