Part A 1-phenylethanol + excess I2 in base followed by acid workup Part B Predic

Question

Part A

1-phenylethanol + excess I2 in base followed by acid workup

Part B

Predict the products of the following aldol condensation. Show the products both before and after dehydration.

http://tinypic.com/r/15a62c/8

Part C
Draw the major organic product formed when the compound shown below undergoes a reaction with (CH3)2CuLi in diethyl ether, followed by aqueous acid.

http://tinypic.com/r/2wdxant/8

Part D

Predict the product of the following aldol condensation followed by dehydration:

http://tinypic.com/r/2jag4ll/8

Explanation / Answer

Part A:

1-phenyl ethanol on reaction with iodine excess in base medium yields phenylacetaldehyde. The reaction can be shown as follows:

C6H5-CH3-CH2-OH( 1-phenylethanol) + I2 -- 2OH-(Base medium) --> C6H5-CH3-CHO ( phenylacetaldehyde) + 2H2O+2I-

Now, since acid is not given so the exact product can not be detected.

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