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retrosynthesis

is this retrosynthesis valid
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Original post by jacksonmeg
is this retrosynthesis valid


I see a few problems if you want the reverse reactions to be viable.
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jacksonmeg
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Original post by charco
I see a few problems if you want the reverse reactions to be viable.


yes the reverse reaction, what are the problems?
Original post by jacksonmeg
yes the reverse reaction, what are the problems?


AFAIK you can't go diazonium --> amine
Original post by jacksonmeg
yes the reverse reaction, what are the problems?


Whether the reverse reaction is possible is irrelevant. The important thing is that the forward reaction is possible. Your main scheme including azide reduction to amine is fine. Your synthesis of benzoyl chloride is no good because "methanoyl chloride" is unstable decomposing to HCl and CO.
(edited 8 years ago)
Original post by TeachChemistry
Whether the reverse reaction is possible is irrelevant. The important thing is that the forward reaction is possible. Your main scheme including azide reduction to amine is fine. Your synthesis of benzoyl chloride is no good because "methanoyl chloride" is unstable decomposing to HCl and CO.


AFAIK the idea of reverse synthesis is to break up the target compound (as shown) in ways which are reversible.i.e. go backwards to seek a reasonable way of going forwards.

If this were not the case then reverse synthesis becomes a random destruction of the target molecule and hence useless in practical (experimental) terms.

Yes, you can treat an amine to get a diazonium salt, as shown in the break down (reverse phase), but you cannot do the reverse reaction, hence it would be irrelevant in a reverse synthesis.

Example: If you are only interested in the reverse reaction then:

target molecule + oxygen --> carbon dioxide + water + nitrogen

would work.
(edited 8 years ago)
Original post by charco
AFAIK the idea of reverse synthesis is to break up the target compound (as shown) in ways which are reversible.i.e. go backwards to seek a reasonable way of going forwards.

If this were not the case then reverse synthesis becomes a random destruction of the target molecule and hence useless in practical (experimental) terms.

Yes, you can treat an amine to get a diazonium salt, as shown in the break down (reverse phase), but you cannot do the reverse reaction, hence it would be irrelevant in a reverse synthesis.

Example: If you are only interested in the reverse reaction then:

target molecule + oxygen --> carbon dioxide + water + nitrogen

would work.


Maybe you have mis-interpreted my post in terms of forward and backwards. The OP uses a retrosynthetic step where they make an azide (it's not a diazonium) from an amine. This is not possible but in the forward sense, the direction in which the synthesis needs to go, azide to amine is possible (using hydrogenation is best, or use PPh3).

I think you have not appreciated that it is an azide not a diazonium.
(edited 8 years ago)
http://www.organic-chemistry.org/synthesis/N1H/reductionsazides.shtm
Original post by TeachChemistry


I was under the impression that the OP had put a diazonium salt not an azide!

I should have looked a little more carefully ..
(edited 8 years ago)

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