[orgo814]

Sorry if this picture is sideways my device has problems uploading correctly.

For this question the answer according to the book is D. I do not see how D is possible. I am getting B when I do this. Thanks for any input

[discodermolide]

Alcohols react with Grignard reagents, what do they produce?

[orgo814]

All I know is they can react into carbonyl adding more C-C bonds

[Dan]

All I know is they can react into carbonyl adding more C-C bonds

What happens if you add water to a Grignard reagent?

[Babcock_Hall]

Are Grignard reagents acidic, basic, or neutral?

[discodermolide]

Grignards are organometallic reagents consequently very reactive towards functional groups with H atoms which can be abstracted to give ...?
Now your molecule has a OH group and an aldehyde, so which is more reactive towards the Grignard reagent?

[orgo814]

So we are proposing that the OH not the aldehyde here and that the de protonated OH group then becomes protonated in the aqueous work up

[Babcock_Hall]

Does your hypothesis explain the side product?

[discodermolide]

So we are proposing that the OH not the aldehyde here and that the de protonated OH group then becomes protonated in the aqueous work up

What happens to the H of the deprotonated OH?

[orgo814]

H added to ch3 of grignard

[discodermolide]

Right, so why is the correct answer (D)? Draw the reactions out.