Question

There are eight constitutional isomers with molecular formula C5H11NO2 that contain a nitro group (-NO2). Seven of these isomers have similar pKa values, while the eighth isomer has a much higher pKa value. Draw all eight isomers, and identify which one has the highest pKa. Justify your logic with a minimum amount of words or a drawing.

Answer 1

Answer:

Explanation:

Seven of these isomers having similar pKa values are as follows

1)  CH₃ -CH(CH₃)-CH(NO₂)-CH₃

2 ) CH₃ -(CH₂)-CH(NO₂)-CH₂-CH₃

3 )  CH₃ -CH₂-CH₂-CH₂-CH₂-NO₂

4 ) CH₃ -CH₂-CH₂-CH(NO₂)-CH₃

5 )CH₃ -CH(CH₃)(NO₂)-CH₂-CH₃

6 ) CH₃ -CH(CH₃)-CH₂-CH₂-NO₂

7)CH₃ -CH₂-CH₂-CH(CH₃)-NO₂

CH₃-C(CH₃)₂-NO₂

The last isomer has different PKa value because of tertiary carbon attached to nitro group.