organic synthesis reactions

[113zami]

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http://i274.photobucket.com/albums/jj243/113zami/orgodd0001-1.jpg

the reactant is benzyl alcohol, the wierd symbol is a benzene ring

so i am trying to find the products to these 2 reactions:

for 1st one,I think there will be no reaction since the closest reaction I found in my text book involving alcohol and Cu is
2ndary alcohol+CuO--->ketone

for the 2nd one
ROH + HCN--->RCN
RCN+ H2O--->primary amide(RCONH2)
primary amide(RCONH2) + NH3--->No reaction

am I correct?? 😕
thanks

 

[harrygt]

http://i274.photobucket.com/albums/jj243/113zami/orgodd0001-1.jpg

the reactant is benzyl alcohol, the wierd symbol is a benzene ring

so i am trying to find the products to these 2 reactions:

for 1st one,I think there will be no reaction since the closest reaction I found in my text book involving alcohol and Cu is
2ndary alcohol+CuO--->ketone

for the 2nd one
ROH + HCN--->RCN
RCN+ H2O--->primary amide(RCONH2)
primary amide(RCONH2) + NH3--->No reaction

am I correct?? 😕
thanks

I have no idea about the first one. Cu is a reducing agent, and that benzylic alcohol can't get reduced more than that. [Not sure anyway]

The second one:

after first step: we have Ph-CH2-CN

second step (hydrolysis of the nitrile) : you get ph-CH2-CO2H [2-phenylethanoic acid]. Remember: the hydrolysis of nitrles gives an amide which is subsequently hydrolized to carboxylic acid. It means you can't really stop the hydrolysis at the step of the production of the amide.

Third step: The reaction of the carboxylic acid and NH3 will give you this amide Ph-CH2-CONH2

 

[DRHOYA]

I have no idea about the first one. Cu is a reducing agent, and that benzylic alcohol can't get reduced more than that. [Not sure anyway]

The second one:

after first step: we have Ph-CH2-CN

second step (hydrolysis of the nitrile) : you get ph-CH2-CO2H [2-phenylethanoic acid]. Remember: the hydrolysis of nitrles gives an amide which is subsequently hydrolized to carboxylic acid. It means you can't really stop the hydrolysis at the step of the production of the amide.

Third step: The reaction of the carboxylic acid and NH3 will give you this amide Ph-CH2-CONH2

I was reading this thread. I like your explanation for the second rxn. That helped me alot. It seems pretty simple once you see enough of these. The first one though.....i'm lost in the dark. Btw, after the second step you have ph-CH2-CO2H.....that CO2H is a C=O with an OH also on the C for a carboxylic acid right???? I just want to make sure its not actual CO2 lol.

 

[harrygt]

🙂

I was reading this thread. I like your explanation for the second rxn. That helped me alot. It seems pretty simple once you see enough of these. The first one though.....i'm lost in the dark. Btw, after the second step you have ph-CH2-CO2H.....that CO2H is a C=O with an OH also on the C for a carboxylic acid right???? I just want to make sure its not actual CO2 lol.

Yes of course. RCO2H is the symbol for carboxylic acids. Then you have an amine reacting with the carboxylic acid to form the amide.