[spicy]

If you had the starting materials, Methyl bromide and ethanol, and these are the only sources of carbon you to carry out the following synthesis. Assume you have access to any non-carbon containing reagents. final product: 3-hydroxy-3-methylbutyraldehyde.

[Dan]

You must show you have attempted the question, this is a Forum Rule.

[spicy]

CH3Br + EtOH  CH3CH2CH2OH +Br-

Okay. let me back up. I apologize for not showing my work....

this is my question at step two: do I need to protect the hydroxy group before adding the ethanol again. Or am I looking at this all wrong. I'm stuck!

[spicy]

CH3Br (Mg) CH3MgBr

(2)CH3Br+CH3CH2OH CH3CH2CH2CH2OH + BR2  CH3C(Br)HCH2CH2OH  (KOH) CH2CCH2CH2OH (1. Cl2 2. H2O)  HOCH2CH(Cl)CH2CH2OH  CH2(O[EPOXIDE])CHCH2CH2OH  (CH3MgBr) CH3C(OH)(CH3)CH2CH2OH  (H2CRO4) CH3C(OH)(CH3)CH2CH2(DOUBLE BOND)O

IN STEP TWO: SHOULD I HAVE A PROTECTION GROUP ON THE HYDROXL GROUP

[Dan]

First: Please take time to format your chemical formulae. Take care to capitalize chemical symbols correctly and make use of the subscript numbers and superscript charges provided in the 'other symbols' menu in the post reply window. For more information about correctly formatting posts, click here.

Your chain extension of ethanol with MeBr is science fiction.

Hint: This looks like a question about carbonyl chemistry. What reactions of carbonyls do you know? How can you make carbonyl compounds from alcohols?