The Student Room Group

Chemistry doubt.

Structural isomerism and stereoisomerism should be considered when answering this question.
Each of the following carbonyl compounds is reacted with NaBH4. The product of each reaction is
heated with Al 2O3 at 600 °C, generating one product or a mixture of isomers.
Which carbonyl compound will produce the most isomers?
A butanal
B butanone
C pentan-3-one
D propanone

Correct Answer : B

Please explain how you do this...
Original post by Me2Peeps
Structural isomerism and stereoisomerism should be considered when answering this question.
Each of the following carbonyl compounds is reacted with NaBH4. The product of each reaction is
heated with Al 2O3 at 600 °C, generating one product or a mixture of isomers.
Which carbonyl compound will produce the most isomers?
A butanal
B butanone
C pentan-3-one
D propanone

Correct Answer : B

Please explain how you do this...


See first, an alcohol will form and upon reaction with Al2O3, alkenes will form. So:-
in A, CH3CH2CH2CH2OH will form and if you dehydrate it, only but-1-ene will form.
in B, CH3CH2CH(OH)CH3 will form and if you dehydrate it, but-1-ene, cis but-2-ene and trans but-2-ene can form.
in C, CH3CH2CH(OH)CH2CH3 will form and if you dehydrate it, cis pent-2-ene and trans pent-2-ene can form.
in D, CH3CH(OH)CH3 will form and if you dehydrate it, prop-1-ene will form.

Hence answer is B as most no. of alkenes formed.
Hope this helps :smile:
(edited 5 years ago)
are you also giving the F/M paper on tuesday?
Reply 3
Original post by ChemISlife123
See first, an alcohol will form and upon reaction with Al2O3, alkenes will form. So:-
in A, CH3CH2CH2CH2OH will form and if you dehydrate it, only but-1-ene will form.
in B, CH3CH2CH(OH)CH3 will form and if you dehydrate it, but-1-ene, cis but-2-ene and trans but-2-ene can form.
in C, CH3CH2CH(OH)CH2CH3 will form and if you dehydrate it, cis pent-2-ene and trans pent-2-ene can form.
in D, CH3CH(OH)CH3 will form and if you dehydrate it, prop-1-ene will form.

Hence answer is B as most no. of alkenes formed.
Hope this helps :smile:


ohhhh!!! Thanks sooo much!!! :heart:
Welcome :smile:

Original post by Me2Peeps
ohhhh!!! Thanks sooo much!!! :heart:
Reply 5
Original post by ChemISlife123
are you also giving the F/M paper on tuesday?

Yeppp... Are you??
yup
Original post by Me2Peeps
Yeppp... Are you??
Alcohols dehydrate easily in the following order: tertiary secondary primary. The stability of the intermediate carbocation can be used to justify the ease with which alcohols can be dehydrated. The higher the stability of the produced carbonation, the faster the reaction.
They are categorized as SN₂ reactions in primary alcohols and SN₁ reactions in secondary as well as tertiary alcohols. Tertiary alcohols tend to be easier to dehydrate and primary alcohols to be the hardest.

Quick Reply

Latest