[RCL circuit]

I have been working on this synthesis problem for two weeks but keep running into dead ends. Any help at all would be appreciated.
Synthesize the following molecule using organic compounds with one or two carbon atoms only (not more) and any inorganic compounds. Must be major products!

                    CH3
                     l
           C2H5--C--CH2Cl
                     l
                    OH

[macman104]

First things, change the OH group.  What ways do you know of making a 3° alcohol?  You can have any two pieces that you want to react and make that OH group.  Post that structure, and we'll talk from there.

[RCL circuit]

I am in Organic I right now so this might be a little frustrating for you. Im sorry!

I would use oxymercuration to yield the markinov product on an alkene. but I also considered using an epoxide in H3O+ to open it up to yield a 1,2 diol than change one of the OH groups by SOCl2 and maybe use an alkyl substitution rxn. Im sorry if I didnt really understand the question. I appreciate the help you are offering.

[macman104]

Hmm...ok, fair enough, those are legitimate answers.  Have you learned about the grignard reaction?

[RCL circuit]

We have studied them a little bit are you suggesting using MgX on a carbonyl compound?

[RCL circuit]

only 1 to 2 carbon containing compounds can be used at a time Im not sure how this would effect the carbonyl compound

[macman104]

Correct.  So, change the alcohol into a carbonyl, and then you need to break off one of the groups.  Can you see one of the groups that you could break off and form a symmetric ketone?

[refid]

Heres my try.. I'm sure I've made errors.. just let me know

[azmanam]

Good question.  It stumped me for a while, too.

Macman, b/c of the primary chloride, I don't think Grignard as the last step will work.  I think halohydrin formation is a more plausible last step.

RCL, I got there in 6 steps starting from acetylene.

refid, I don't see a scheme for your post.

[refid]

azmanam, can you tell where I went wrong in my reaction?

[azmanam]

I don't think your enamine chlorination will be selective, and you might see unwanted byproducts when you subject the choride to acidic conditions in your final step.  Creative, though.

[macman104]

azmanam, what if you start with the alpha-chloride?  The Cl shouldn't interfere with a grignard if you start with ClCH₂CHO.  Add, MeMgBr, oxidize, add EtMgBr, no?

[azmanam]

Sure, the carbonyl carbon is electrophilic, probably the most electrophilic, but the chloride-bearing carbon is also electrophilic.  I think you might see competition with S_N2 substitution.

(edit: although Scifinder says this JOC paper from 1981 says you can react allyl Grignard with chloroacetaldehyde to get the halohydrin in 80% yield, so your way might work as well: http://dx.doi.org/10.1021/jo00318a019)

4,5-Epoxy-1-pentene. Allylmagnesium bromide was reacted with chloroacetaldehyde, and the resulting chlorohydrin, bp 65-70 "C (16-17 mm) (lit.27b p 163 "C), was obtained in 80% yield. Cyclization with NaOH gave 4,5-epoxy-1-pentene, bp 92-94 "C (lit.27b p 93.5 "C), in 71% yield (99% purity).

I did acetylene -> propyne -> propene -> methyloxirane --(H⁺, EtMgBr)--> 2-methyl-1-butanol  --(SOCl₂)--> 1-chloro-2-methylbutane  --(NaOEt, EtOH, heat)--> 2-methyl-1-butene  --(Cl₂, H₂O)--> pdt.

Your way's shorter.

[BlowUpEverything]

What about addition of ClOH across a double bond?

[azmanam]

What about addition of ClOH across a double bond?

2-methyl-1-butene  --(Cl2, H2O)--> pdt.

that's what this last step does.  Cl₂ and H₂O make ClOH in solution.