Organic Doubts

1)Why can the use of high temperatures in the catalytic hydrogenation of alkenes to alkanes be self-defeating ?

2)Provide an explanation for the fact that all trans-1,2,3,4,5,6-Hexaisopropylcyclohexane is a stable molecule in which all isopropyl groups are axial.

20 Answers

11
Khyati ·

2)Provide an explanation for the fact that all trans-1,2,3,4,5,6-Hexaisopropylcyclohexane is a stable molecule in which all isopropyl groups are axial.

Ans:- The shape of the isopropyl group is such that it fits more readily, and consequently with less steric interaction, when all the groups are axial.

11
Khyati ·

dbt cleared, thanks to qwerty [1]

11
Khyati ·

Is 2- Bromobicyclo[1.1.0]butane capable of existing as enantiomer?

I drew its structure and I think it is capable of forming enantiomer because 2 carbons (upper and below one) has 4 different groups attcahed.

just clear my doubt

11
Khyati ·

Maximum enolisation ka ek question tha, but I wanted to know the reason, because of this reason I can now solve other problem related to that. [1]

Thanks Prats [3][1]

39
Pritish Chakraborty ·

o-nitrophenol is most volatile because of chelate formation due to H-bonding(between oxygen of -NO2 and H of -OH).

Maximum enolisation? Any specific situation or is this a general question? The enol form is preferred if there is some stabilizing factor which gives greater stability than if the compound were present in keto form, for eg - aromaticity.

11
Khyati ·

Some more questions

a)What is the condition for the maximum enolisation to take place?

b)Which is most volatile isomer of nitrophenol ? why?

11
Khyati ·

Thanks Pritish, I got the explanation now. Nice images

39
Pritish Chakraborty ·

Khyati, this image may help you to gauge the explanation of question 2 -:

And you've asked Q1 around in other forums also. I posted something similar on why elimination is favoured at higher temperatures...if I find the link of the thread I'll paste it here.

23
qwerty ·

[3]

39
Pritish Chakraborty ·

I guess I'm too late here :P

11
Khyati ·

Where are you Pritish? Please help me out in organic [2]

11
Khyati ·

Wow Qwerty, kya mast explanation diya hai. Thanks a lot [1]

23
qwerty ·

remove all possible H, and then check the conjugate bases for each H.
the most stable base will result frm most acidic H.wat venkatesh said is correct , but only when all other important factors arent present.

but in a cyclopentadiene, resonance is possible. now when the H from sp3 carbon will be removed , we get a planar comp with 6 delocalised π electrons . hence the resulting anion is aromatic , which makes it highly stable.

11
Khyati ·

Thanks Abhishek [1]

11
Khyati ·

Arey but in the answer they have given the hydrogen attached to sp3 carbon acidic

See the arihant organic chemistry textbook, page no. 16 question no.4 (b) and (c)

1
Abhisek ·

Ans 4:

The dotted lines show hydrogen bonds....

1
venkateshan ·

the H attached to the sp hybridized atom is more acidic than sp2 hybridized and sp3 hybridized....

Acidic order :

sp H > sp2 H > sp3 H

11
Khyati ·

Some more questions

3) How to know the acidic hydrogen in the compounds in which hydrogen is attached to the atom other than oxygen, for example in Cyclopent-1,3-diene?

4)Why only 4 water molecules are directly attached to one water molecule? I know its a stupid question, but I cannot think of a reason for it.

11
jeetopper jee ·

@khyati yup the reason given by you is perfectly right.i asked it from a senior

11
Khyati ·

1)Why can the use of high temperatures in the catalytic hydrogenation of alkenes to alkanes be self-defeating ?

ΔG = ΔH - TΔS

Because the higher the temperature, the more likely a dehydrogenation back to the alkene will take place!

http://www.chemicalforums.com/index.php?topic=43918.0

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