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Proton NMR - structure question

Hey guys, got a question!

I've been doing this NMR question, and have the ester 'reversed' to what's in the mark scheme.

Could someone be able to explain how to get the correct ester structure, not the reversed one, like I have?

Here's the question and the mark scheme for the structure:

Cheers in advance guys!

1401820147934.jpg
1401820174250.jpg
Original post by KiddingMe
Hey guys, got a question!

I've been doing this NMR question, and have the ester 'reversed' to what's in the mark scheme.

Could someone be able to explain how to get the correct ester structure, not the reversed one, like I have?

Here's the question and the mark scheme for the structure:

Cheers in advance guys!

1401820147934.jpg
1401820174250.jpg


(i) You have a 9 proton singlet. This must come from a tertiary butyl group C(CH3)3

(ii) You then have a 3 proton at 1.4 coupled with a 2 proton at 4.2

This is indicative of CH3CH2 attached to something electronegative.

(iii) There is also a 2 proton singlet at 2.2, i.e. not coupled with anything - next to the tertiary butyl carbon.

So the (ii) suggests that this is the oxygen end of the ester, i.e. CH3CH2-O-CO-CH2C(CH3)3

or written the other way round:

(CH3)3CCH2-COO-CH2CH3
(edited 9 years ago)
Reply 2
Original post by charco
(i) You have a 9 proton singlet. This must come from a tertiary butyl group C(CH3)3

(ii) You then have a 3 proton at 1.4 coupled with a 2 proton at 4.2

This is indicative of CH3CH2 attached to something electronegative.

(iii) There is also a 2 proton singlet at 2.2, i.e. not coupled with anything - next to the tertiary butyl carbon.

So the (ii) suggests that this is the oxygen end of the ester, i.e. CH3CH2-O-CO-CH2C(CH3)3

or written the other way round:

(CH3)3CCH2-COO-CH2CH3



Hey, cheers for that info! Made a splitting mistake now that I look back.

Thanks again!

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