The following questions deal with epoxide formation. (Show proper stereochemistr

Question

The following questions deal with epoxide formation. (Show proper stereochemistry when you answer these questions.)

I have answered the first 3 parts to this question correctly. I just need help with part D.

(a) Draw the skeletal structure of (Z)-3-methyl-2-pentene.

(b) Draw the skeletal structure of one of the enantiomers formed when (Z)-3-methyl-2-pentene reacts with Br2 in the presence of water.

(c) Draw the skeletal structure of the epoxide formed from your product (b) when it reacts with sodium hydroxide.

(d) Draw the skeletal structure of the major organic product from (c) when it reacts with sodium methoxide in methanol-water solvent followed by an acid workup. (Hint: Experimental data indicate that the elimination product is not the major organic product.)

Please help me with this answer (question D). The drawing that I have below It is incorrect - (2S,3S)-3-methylpentane-2,3-diol.

Please note the question asks for for the product formed from the answer in C, not product B like some other similar questions to this. Thank you for your help.

Explanation / Answer

OH
|
CH3-C-CH-CH2CH3
|
O

|   
CH3

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