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October 22, 2011 | | Comments 0

You Asked About: 1h Nmr Table

Steven asks…

draw the skeletal structure of isomer #2?

Question Details:
There are two different constitutional isomers that have the same multiplicity of signals for their protons, but at different chemical shifts, as shown in the table below. Use the chemical shift information given in Table A and Table B to help you determine the structure of the indicated isomer whose structure would be consistent with the information given below.
Hint: the table gives approximate chemical shifts. It is possible for the chemical shift of a proton bonded to an atom or functional group shown in Table A to be outside of the range given if that proton could fall into 2 different categories on the table.)
molecular formula: C4H7ClO2.
1H NMR:
Isomer #1unknown_prefix
Isomer #2unknown_prefix

Singlet @ 4.34 ppm

Quartet @ 4.12 ppm

Triplet @ 1.30 ppm
Singlet @ 6.17 ppm

Quartet @ 2.29 ppm

Triplet @1.14 ppm

Diagnostic IR peak for both isomers is consistent with the functional group whose peak lies between 1730 – 1750 cm-1
SODAR = 1
(SODAR stands for sum of double bonds and rings. A SODAR of 1 means there is either 1 bond or 1 ring. A SODAR of 2 means there are: 2 bonds or 2 rings or 1 bond and 1 ring.)

Chas answers:

A: CH3CH2O2CCH2Cl

b: CH3CH2CO2CH2Cl

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