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Organic Chemistry - Reaction Help

Hello :smile:

I've been stumped on this reaction (refer to attachment) for over a day now and I can't seem to predict the product for this reaction. The resulting product you get is then supposed to undergo a reaction with an acid chloride (propanoyl chloride) to yield a pair of enantiomers.

Now according to my textbook, E2 is favoured when you have a strong base and strong nucleophile with a secondary substrate (-OH) and SN2 is the minor product, however the next step in the synthesis is not possible because there is no Lewis acid catalyst with the propanoyl chloride (such as AlCl3) so I assume Friedel-Crafts Acylation is out of the question with the benzene ring.

Will the SN2 reaction in this case dominate? If so, why??? I can predict -OH will replace chlorine and then the lone pair of the OH will attach to the acid chloride (in the final step) forming an ester once the chloride is kicked off.

Any help or suggestions please?? Thanks
(edited 9 years ago)
organic help.png12.4KB
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