Halogenoalkane mechanism question please

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anactualmess
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Q10.Which one of the following types of reaction mechanism is not involved in the above sequence?
CH3CH2CH3 -----> (CH3)2CHCl --------> (CH3)2CHCN -------> (CH3)2CHCH2NH2 ------> (CH3)2CHCH2NHCOCH3


A free-radical substitution
B nucleophilic substitution
C elimination
D nucleophilic addition-elimination

I know that free-radical substitution is involved because an alkane is being converted to a halogenoalkane, and nucleophilic substitution is involved because a halogenoalkane is being converted to a nitrile, but after that I'm lost
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username3249896
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(Original post by anactualmess)
Q10.Which one of the following types of reaction mechanism is not involved in the above sequence?
CH3CH2CH3 -----> (CH3)2CHCl --------> (CH3)2CHCN -------> (CH3)2CHCH2NH2 ------> (CH3)2CHCH2NHCOCH3


A free-radical substitution
B nucleophilic substitution
C elimination
D nucleophilic addition-elimination

I know that free-radical substitution is involved because an alkane is being converted to a halogenoalkane, and nucleophilic substitution is involved because a halogenoalkane is being converted to a nitrile, but after that I'm lost
Nucleophilic addition-elimination when nitrile is hydrolysed and the last condensation reaction

answer is C
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Pigster
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(Original post by anactualmess)
Q10.Which one of the following types of reaction mechanism is not involved in the above sequence?
CH3CH2CH3 -----> (CH3)2CHCl --------> (CH3)2CHCN -------> (CH3)2CHCH2NH2 ------> (CH3)2CHCH2NHCOCH3


A free-radical substitution
B nucleophilic substitution
C elimination
D nucleophilic addition-elimination

I know that free-radical substitution is involved because an alkane is being converted to a halogenoalkane, and nucleophilic substitution is involved because a halogenoalkane is being converted to a nitrile, but after that I'm lost
Do you know what reaction is happening in the last step? Does it look like C or D?
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Kallisto
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(Original post by anactualmess)
Q10.Which one of the following types of reaction mechanism is not involved in the above sequence?
CH3CH2CH3 -----> (CH3)2CHCl --------> (CH3)2CHCN -------> (CH3)2CHCH2NH2 ------> (CH3)2CHCH2NHCOCH3


A free-radical substitution
B nucleophilic substitution
C elimination
D nucleophilic addition-elimination

I know that free-radical substitution is involved because an alkane is being converted to a halogenoalkane, and nucleophilic substitution is involved because a halogenoalkane is being converted to a nitrile, but after that I'm lost
Advice you to look at the reactions steps carefully. What happened in the first reaction? is this a substitution or addition? same goes for the next reaction steps. Did it came to elimination? where in the reactions did it come to free-radical, if any? are there nucleophilic reactions possible?

I would suggest you to write in lewis formula to have an overview to the structures. That makes it certainly easier for you to get the mechanisms out.
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