DAT Destroyer OC Question

[hope_to_match]

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From 2013, Question # 241. Im looking at the explanation and I don't understand why 1-propanamine is formed? I thought the NH2NH2 is a Wolff Kishner that reduces carbonyl and adds two H's. So how come in this problem, the benzene ring and all is lost and we are only left with propanamine? 😕

 

[LazyP]

I am confused on it myself but I figure its probably after the carbonyl reduces, NH2NH2 will attack the C-N bonds and cause the N group to leave on both ends since its not a C-C bond.

 

[hope_to_match]

i love how he says 'this is a simple sn2 reaction' lmao

 

[nutritiousfoods]

The reaction is called the Gabriel synthesis. You basically get a 1* amine out of the reaction.

 

[LazyP]

I know right! To him its "simple" as the nucleophile will attack the partially positive C attached to N after reducing carbonyl. Thats two times, no body got time for that!

 

[Jay20155555]

for Gabriel synthesis, why is the first part a SN2 reaction? The nucleophile is "bulky" so wouldnt it be more likely to be E2 or SN1?