phenylethanone

how can phenylethanone be converted into 1- phenylethanol?
would it be a Grignard reaction or a reduction reaction using sodium tetrahydridoborate NaBH4
if it is a Grignard reaction what grignard reagant would you use

Reply 1

vinny221

What is 'phenylethanone'? Do you mean benzaldehyde?

Reply 2

No Future

You're just reducing the side chain (the non benzene bit) so just use a reducing agent e.g. NaBH4 (or LiAlH4), in dry ether followed by HCl.

The reason why you use the reducing agent and not a Gringard is that the conversion is from ethanone to ethanol, hence no change in the length of the carbon chain. Gringard reactions usually involve an increase in chain length.

Reply 3

No Future

vinny221

What is 'phenylethanone'? Do you mean benzaldehyde?

Same compound, different name?

Reply 4

voleman

I think he means http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=10382743

Just using LiAlH4 of NaBH4 would reduce it to 1-phenylethan-1-ol.

Reducing benzaldehyde in the same way would give phenylmethanol.

LiAlH4 in dry ether.

No Future

Same compound, different name?

phenylethanone= C6H5COCH3
benzaldehyde = C6H5CHO

Reply 7

cpchem

Products of lithal reduction being 1-phenylethanol and benzyl alcohol respectively.

Reply 8

ChemClues

phenylethanone refers to the O being on a middle carbon as apposed to an end carbon changing to aldehyde.

Reply 9

riashat

Reduce phenylethanone with zinc and hydrochloric acid??

it says so in the textbook answers.

Reply 10

EquableClover

Phenylethanone is Acetone, Benzene with an ethanone group attached to it where as benzaldehyde is just benzene with an aldehyde group attatched to it. Similar, but different, things.