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Chemistry Level 5

Which of the following statements related to Cyclohexane \text {Cyclohexane} are correct ?

1 - H a l f Half C h a i r Chair conformer of cyclohexane is most stable.

2 - B o a t Boat f o r m form conformer of cyclohexane has angle strain .

3 - H a l f Half C h a i r Chair conformer of cyclohexane is free from angle strain.

4 - Cyclohexane has the lowest heat of combustion compared to other cycloalkanes ( eg: cyclopropane, cyclobutane etc.).

5 - The stable form of cis-1,2-dimethylcyclohexane(Chair form) is (1e, 2e ). [ e e q u a t o r i a l [e-equatorial , a a x i a l p o s i t i o n ] a-axial position] .

6 - The stable form of c i s 2 m e t h y l c y c l o h e x a n o l cis-2-methylcyclohexanol (Chair form) is [1a (Me) , 2e (OH)].

7 - The stable form of c y c l o h e x a n e 1 , 4 d i o l cyclohexane-1,4-diol is boat form.

10 - 1 , 4 d i m e t h y l c y c l o h e x a n e 1,4-dimethylcyclohexane is optically active.


Enter your answer as the product of the respective option numbers of correct response.

Clarification \text {Clarification} : If you think statements 2,3 and 5 are true, enter your answer as 2 × 3 × 5 = 30. 2 \times 3 \times 5 = 30.


This is a part of my set Aniket's Chemistry Challenges . (BEST OF JEE - ADVANCED)


The answer is 189.

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2 solutions

Aniket Sanghi
Apr 24, 2016

Correct answers are 3,7,9.......

  • All the conformer of cyclohexane are Free from angle strain.

  • Stability order of conformer are Chair > Twisted boat > Boat > Half Chair.

  • Cyclohexane has the lowest heat of combustion per C H X 2 \ce{CH2} group.

  • cis-1,2-dimethylcyclohexane can be ( a , e ) (a,e) or ( e , a ) (e,a) . ( e , e ) (e,e) is for trans.

  • 6th option : Methyl is bulky and must be in equatorial position for stability.

  • 7th option is correct as in that position their is H H - bonding stability.

  • To find R , S R,S configuration , see the carbon such that the least prior group is seen farthest. Then start making circle starting from highest prior group to least prior group .........Then R configuration is for clockwise and S configuration is for anticlockwise.

If you like it then ..... Like it!! Share it!! And upvote the solution

Aniket Sanghi - 5 years, 1 month ago

Nicely explained Aniket:)

Gauri shankar Mishra - 5 years, 1 month ago

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Won't you like to like and reshare the q ......I am surprised to see that the q isn't got the rating

Aniket Sanghi - 5 years, 1 month ago

Were you able to solve ,

Aniket Sanghi - 5 years, 1 month ago

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Yes i was able to solve it but in the 2 nd try :(

Gauri shankar Mishra - 5 years, 1 month ago

I don't think that half chair conformer has no angle strain. Half chair is formed by pulling one end of flat cyclohexane up, so one end still remains flat and should have bond angle of 120 degrees, thereby causing angle strain

You may see http://www.masterorganicchemistry.com/2014/04/18/ring-strain-in-cyclopentane-and-cyclohexane/

Also in 7th option why can twist boat conformation be not stable? ( i think H bonding is also possible in twist boat)

I am not so good in chemistry as u guys are so it would be helpful if you could clear my doubts

Hargun Preet Singh - 5 years, 1 month ago

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All the conformers of cyclohexame are free from angle strains the only cause of instability is the conformational arrangement as I have learned up till now! From (cengage, MS Chouhan).

Their is no 120degree in half chair , all are 109.5° (which is easily possible) its not that symmetry as we draw them in copy

Abt boat conformer, my book says(I agree with it) that in boat conformer the stable form of it is in 1a,4a and on the upward directed 2 triangles (very nice H-bonding takes place here).

If you are still not satisfied , you are free to ask :)

Aniket Sanghi - 5 years, 1 month ago

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Can you please tell me the exact structure of half chair conformer which allows all bond angles to be 109.5 degree?

Hargun Preet Singh - 5 years, 1 month ago

4 is correct. That's the reason for coming up with non-planar theory

Vignesh S - 5 years, 1 month ago

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No man ! Do read the 3rd point of my solution

Aniket Sanghi - 5 years, 1 month ago

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I read it but I still remember it was correct. OK if you say so

Vignesh S - 5 years, 1 month ago
Siddharth Shourya
May 30, 2016

Ankiet keep posting such type of questions they are really awesome

Thanks! :) and Sure!

Aniket Sanghi - 5 years ago

I hope that u all also post challenging questions for me :)

Aniket Sanghi - 5 years ago

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