[jessica145]

So I have a final exam tomorrow and I am having ALOT of trouble doing the problems from the practice exam he gave us. And I am very worried because the practice exams are usually just like our tests!

Can somebody please Help me with these problems if I provide pictures??

1.Show complete mechanism and curly arrows:
https://www.t-mobilepictures.com/myalbum/thumbnail/photo16/de/a3/d321700c309c__1273166404000.jpeg?tw=315&th=210&s=true

2. Predict product and propose mechanism, curly arrows:
https://www.t-mobilepictures.com/myalbum/thumbnail/photo03/86/49/85905d277ebc__1273166464000.jpeg?tw=315&th=210&s=true

3. How do you synthesize 1-hexanol from acetylene? Show all reagents, solvents and intermediates:
https://www.t-mobilepictures.com/myalbum/thumbnail/photo27/fd/05/29f31f723fac__1273166385000.jpeg?tw=315&th=210&s=true

4.How do you synthesize 1,4 dioxane from 1,2 dichloroethane? Show all reagents and intermediates:
https://www.t-mobilepictures.com/myalbum/thumbnail/photo17/b1/9d/71a235201743__1273173998000.jpeg?tw=315&th=210&s=true


If you can help me with any of these i will greatly appreciate it!!! Especially numbers 1-3! pleaseee!, more so 1 & 3 bc they are what i have trouble with

[Borek]

Please read forum rules.

[Doc Oc]

Jessica, I hope you now realize that this is the worst possible way to study and that you work much, much harder if you make it into the next series of o. chem.  I'm not going to solve the problems for you, but I will give you hints.  The rest is up to you.

1) After protonation, there's a shift that occurs to stabilize the carbocation.

2) SN1 reaction.

3) Too many possibilities to narrow in on one.  Off the top of my head, try a Lindlar's reduction to get the alkene, then halohydrin formation to give the 1,2-halogen alcohol.  Then you can either try to convert your product to a Grignard and add to butyl halide or add butyl Grignard to yours (yes, I know this will deprotonate the alcohol too, no comments!)

4) Williamson ether synthesis with a diol.