[phil14:3]

Probably somone here can help me out.. This is not my hw lol. its actually part of my finals which I never got to answer.. ugh it got me frustrated.

1. starting with 1-chloropropane formaldehyde and butanone, synthesize 2-methyl-2-ethylpropanal

2. starting with ethyne, synthesize (2S,2R) 3,4-hexanediol

[Jorriss]

For the first, I'd probably use 2-chloropropane and make a grignard then attack formaldehyde and then oxidize it with pcc.

For the second, is your issue the whole process or just the stereochemical issues?

Btw, generally on forums you want to avoid caps lock

[Schrödinger]

1. starting with 1-chloropropane formaldehyde and butanone, synthesize 2-methyl-2-ethylpropanal

Are you sure that's the product? 2-methyl-2-ethyl propanal is actually 2,2-dimethylbutanal. givent

@ Joriss : What would your final product be? Moreover, you are not allowed to use 2-chloropropane, you've got to start from the 3 given compounds

[Jorriss]

1. starting with 1-chloropropane formaldehyde and butanone, synthesize 2-methyl-2-ethylpropanal

Are you sure that's the product? 2-methyl-2-ethyl propanal is actually 2,2-dimethylbutanal. givent

@ Joriss : What would your final product be? Moreover, you are not allowed to use 2-chloropropane, you've got to start from the 3 given compounds

Woops, I read 2-chloro instead of 1-chloro.

Ok, Step 1: Change 1-chloropropane to 2-chloropropane

And I'm pretty sure the major product of my sequnce is what was wanted.

[phil14:3]

For the first, I'd probably use 2-chloropropane and make a grignard then attack formaldehyde and then oxidize it with pcc.

For the second, is your issue the whole process or just the stereochemical issues?

Btw, generally on forums you want to avoid caps lock

For the second, I can't seem to figure outhow the whole process should work out..

I'm sorry for the caps lock. haha

[phil14:3]

1. starting with 1-chloropropane formaldehyde and butanone, synthesize 2-methyl-2-ethylpropanal

Are you sure that's the product? 2-methyl-2-ethyl propanal is actually 2,2-dimethylbutanal. givent

@ Joriss : What would your final product be? Moreover, you are not allowed to use 2-chloropropane, you've got to start from the 3 given compounds

I'm pretty sure that was the given product for the mechanism...

[Jorriss]

Ohhhh snap, I did some dumb stuff lol. I misread what type of propane we had AND miswrote the product. Scratch what I said before.

Man, I'm bustin' my head now, I don't see the first one. I'm going to keep thinking though...

[democanarchis]

For the second, its a similar thought process to the first, except it takes a bit longer. How would you make a digrignard from that starting material?