Neuman stability and chiral question

[Puchinita5]

Homework Statement

I have two questions. I have attached two pictures, 1 for each.

1. For the question about stability, the answer is C, but I thought it should be B. I would imagine the strain of two OH groups would be greater than an OH group with a CH3 group. Can someone explain what is wrong in my thinking?

2. For the question about chirality, the answer is C. I don't see how any of them can be chiral, but I guessed D because the N in II is at least sp3 because of a lone pair of electrons. I don't see any sp3 carbons in III except in the CH3 group, but that is not chiral because the three H's are the same.

These questions are from my ACS organic review book.

Thank you for your help!

Homework Equations

The Attempt at a Solution

 

[sjb-2812]

Homework Statement

I have two questions. I have attached two pictures, 1 for each.

1. For the question about stability, the answer is C, but I thought it should be B. I would imagine the strain of two OH groups would be greater than an OH group with a CH3 group. Can someone explain what is wrong in my thinking?

2. For the question about chirality, the answer is C. I don't see how any of them can be chiral, but I guessed D because the N in II is at least sp3 because of a lone pair of electrons. I don't see any sp3 carbons in III except in the CH3 group, but that is not chiral because the three H's are the same.

These questions are from my ACS organic review book.

Thank you for your help!

Homework Equations

The Attempt at a Solution

For 2, what happens if you exchange the methyl group and the proton attached to the same carbon. Can you superimpose this on your original?

 

[Puchinita5]

I'm sorry I'm not sure what you mean ? :-/

 

[sjb-2812]

OK, how do you know that cis and trans but-2-ene are different compounds?

 

[Puchinita5]

Because they have different physical properties? lol I feel I am missing something.

 

[Puchinita5]

Hmmm okay so I see now what you mean by exchanging the methyl and proton. And you wouldn't be able to superimpose these. Is that what makes them optically active? So it doesn't matter that there are no "chirality centers? "

 

[Puchinita5]

Oops I just realized, i mistyped. The answer to the stability question is D, not C. And I think the answer should be A. Why is the answer not A? (When I originally posted I had said I thought the answer should be B but this was because I ordered my choices backwards. I really meant A) But I still don't understand why for the same reason. But just in case anyone was really confused. :)