can someone check this orgo q for me?

[RUpremed]

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hi guys,

so i just went through an orgo question. i'm pretty sure the method i have is correct, but i'd appreciate it if someone could double check it...

1. propose a method to go from RCOOH to RNH2

I said to....first treat it with SOCl2, then attack it with NH3, and lastly reduce it using LAH..

but the book said to

use SOCl2, use NaN3 (using Curtius rearrangement, which i'm not familiar with, and lastly, treat it with water...

is my method correct?

 

[2PacClone23]

Yeah your method works.



Can't you also use CN and then reduce it to get the desired product? (Although I think doing CN adds an extra carbon)

 

[TK2006]

hi guys,

so i just went through an orgo question. i'm pretty sure the method i have is correct, but i'd appreciate it if someone could double check it...

1. propose a method to go from RCOOH to RNH2

I said to....first treat it with SOCl2, then attack it with NH3, and lastly reduce it using LAH..

but the book said to

use SOCl2, use NaN3 (using Curtius rearrangement, which i'm not familiar with, and lastly, treat it with water...

is my method correct?

Your method is slightly off.

Your method: RCOOH --> acyl chloride (RCOCl) --> amide (RCONH2) --> primary amine (i.e. R-CH2-NH2). You are getting an extra carbon in the middle between -R and -NH2. This is not what the problem is asking for.

Book's method: RCOOH --> acyl chloride (RCOCl)--> acyl azide (RCON3) --> primary amine (R-NH2) and CO2 generated as a result of Curtius rearrangment (i.e. losing the carbonyl group totally). R-NH2 here is the desired product.

 

[TK2006]

hi guys,

so i just went through an orgo question. i'm pretty sure the method i have is correct, but i'd appreciate it if someone could double check it...

1. propose a method to go from RCOOH to RNH2

I said to....first treat it with SOCl2, then attack it with NH3, and lastly reduce it using LAH..

but the book said to

use SOCl2, use NaN3 (using Curtius rearrangement, which i'm not familiar with, and lastly, treat it with water...

is my method correct?

You can also change one thing in your method and it will work.

1. SOCl2 (makes RCOCl)
2. NH3 (makes RCONH2)
3. Br2, NaOH (makes R-NH2 and CO2 via Hoffman Rearrangment)

Anway, your goal is to lose that carbonyl carbon! 🙂

 

[rnbaxter]

misread and not workin through again others are correct above