[earbmu]

Hi 
Can someone double check my work please. This chapter of the book is difficult ;P
Here is the question
http://img253.imageshack.us/img253/3254/untitled1iy8.png

and this is my answer.
http://img264.imageshack.us/img264/5640/picture2sc0.jpg

Thanks in advance.

[PRIYA1022]

Hi,
  I think your reaction d) would not work....You have a tertiary alkyl halide and an SN2 reaction on it would be very difficult.
For b).. a friedal Crafts acylation on benzene to get acetophenone, followed by a Grignard reation on it with cyclohexyl magnesium bromide.

[Custos]

Your answer to B is never going to work  

There's a problem with C. The product has a three carbon chain and you have only introduced a second carbon with the addition of cyanide. I'm not sure what the question is after but I would probably go with a malonic ester synthesis (see below).

[PRIYA1022]

Why do u think b) would not work?
Any way how about  phenyl lithium reacting with cyclohexyl methyl ketone?

[english]

Why do u think b) would not work?

Typically, frowns don't get you far. 

[Custos]

Why do u think b) would not work?
Any way how about  phenyl lithium reacting with cyclohexyl methyl ketone?

I didn't mean your solution to B (which is exactly the answer I would have given) but the one originally posted - the frown. I was just kidding.

[refid]

For C

Would this work ?

[english]

An alternative to PCC treatment is Swern oxidation.

[Custos]

And a shortcut to the alcohol would be to make a Grignard out of the benzyl bromide and react it with ethylene oxide. Lots of ways of getting the final product. 

[english]

And a shortcut to the alcohol would be to make a Grignard out of the benzyl bromide and react it with ethylene oxide. Lots of ways of getting the final product. 

I would much more prefer that method.  Far fewer steps.