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Chemistry MCQ help please

I can’t give the whole question sorry idk how to upload it but the answer says that a halogenoalkane undergoes addition polymerisation which i don’t think is correct and also that the reaction of this halogenoalkane with sodium cyanide followed by hydrolysis of the resulting product gives a carboxylic acid is incorrect. I thought this would happen. If someone could explain that’d be great, thanks.

Reply 1

Original post by jarvisanna
I can’t give the whole question sorry idk how to upload it but the answer says that a halogenoalkane undergoes addition polymerisation which i don’t think is correct and also that the reaction of this halogenoalkane with sodium cyanide followed by hydrolysis of the resulting product gives a carboxylic acid is incorrect. I thought this would happen. If someone could explain that’d be great, thanks.

Are you sure it was a haloalkane or haloalkene

Reply 2

Original post by jarvisanna
I can’t give the whole question sorry idk how to upload it but the answer says that a halogenoalkane undergoes addition polymerisation which i don’t think is correct and also that the reaction of this halogenoalkane with sodium cyanide followed by hydrolysis of the resulting product gives a carboxylic acid is incorrect. I thought this would happen. If someone could explain that’d be great, thanks.

Hello jarvisanna!

You are right about the lack of precision in the answer.

1.

Haloalkanes with a sigma bond don't polymerise by addition like haloalkenes. No pi bonds...no addition!

2.

Haloalkenes with pi bonds polymerise by addition.

3.

The reaction of a haloalkane with NaCN doesn't give a carboxylic acid but a nitrile (R-CN).

These little tips can get you on the right track to reanalysing the whole exercise.
Bye,
Sandro
(edited 6 months ago)

Reply 3

Original post by jarvisanna
I can’t give the whole question sorry idk how to upload it but the answer says that a halogenoalkane undergoes addition polymerisation which i don’t think is correct and also that the reaction of this halogenoalkane with sodium cyanide followed by hydrolysis of the resulting product gives a carboxylic acid is incorrect. I thought this would happen. If someone could explain that’d be great, thanks.


Halogenoalkanes do not undergo polymerisation - there would have to be other functional groups on the molecule for that to be a possibility. Addition polymerisation requires there to be isolated C=C bonds present in the molecule (e.g think alkenes).

If a haloalkane reacts with NaCN, it gives a nitrile. Nitriles can be hydrolysed one of two ways:

(1) Heating under reflux with an aqueous strong acid, which produces a carboxylic acid, plus an ammonium salt as a co-product.

(2) Heating under reflux with an aqueous strong base, which produces a carboxylate salt, plus ammonia as a co-product. The carboxylate salt can be converted to a carboxylic acid upon the introduction of a strong acid.

I’d need to see the full question and your rationale to understand what the problem is with the second question.
(edited 6 months ago)

Reply 4

Original post by TypicalNerd
Halogenoalkanes do not undergo polymerisation - there would have to be other functional groups on the molecule for that to be a possibility. Addition polymerisation requires there to be isolated C=C bonds present in the molecule (e.g think alkenes).
If a haloalkane reacts with NaCN, it gives a nitrile. Nitriles can be hydrolysed one of two ways:
(1) Heating under reflux with an aqueous strong acid, which produces a carboxylic acid, plus an ammonium salt as a co-product.
(2) Heating under reflux with an aqueous strong base, which produces a carboxylate salt, plus ammonia as a co-product. The carboxylate salt can be converted to a carboxylic acid upon the introduction of a strong acid.
I’d need to see the full question and your rationale to understand what the problem is with the second question.

Thank you that's really helpful. I understand now.

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