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Does ammonolysis of primary and secondary alkyl halides proceed through SN2 mechanism?

We know that the first the ammonia acting as nucleophile attack the alkyl halide forming the substituted ammonium salt, but my question is why cannot it proceed through a typical $S_\text N2$ type, ...
green_32's user avatar
  • 268
6 votes
2 answers
570 views

Do alkyl halides with an alpha nitrogen atom undergo SN1 reaction?

Today, in my organic chemistry class, I learnt about the nucleophilic substitution reaction. The notes have stated that: Alkyl halides with $\alpha$ oxygen atom can also undergo SN1 reaction ...
Tan Yong Boon's user avatar
0 votes
1 answer
999 views

Safest Methylating Agent

I am planning on doing some synthesis in the near future and due to safety purposes I am looking for a methylating agent that is both effective and safe. The substrate is a deprotonated amine and the ...
AS_1000's user avatar
  • 1,654
4 votes
1 answer
626 views

Why is ammonium chloride rather than an alkylammonium chloride salt the product of nucleophilic substitution of a chloroalkane by ammonia?

My textbook said that when an excess of ethanolic ammonia is heated with a haloalkane ($\ce{R-X}$) one should give the products as being $\ce{R-NH2}$ and $\ce{NH4Cl}$ as opposed to $\ce{RNH3Cl}$. I ...
lamantin's user avatar
3 votes
1 answer
5k views

What are the conditions for making amines from alkyl halides?

From what I understand, to make an amine from an alkyl halide you need to heat the alkyl halide with a mixture of ammonia and ethanol. I have two questions: Do both ammonia and ethanol need to be ...
Meep's user avatar
  • 1,697