TBR test 2 biological sciences q 96

[2010premed]

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What is the MOST likely side product to be produced when a silyl protecting group is treated with acidic water to reform an alcohol?

A. R3SiOH
B. R2SiO
C. R2SiO2
D. R3SiO2

Answer: A

Anyone have a good explanation?

 

[Rabolisk]

Seems like the only alcohol to me..

 

[2010premed]

Right, but why should the side product have alcohol?

 

[Rabolisk]

Because the question says so, and because it's like an ether being cleaved.

 

[2010premed]

Yeah, but the question is asking for the side product, not the original alcohol

 

[Pons Asinorum]

Yeah, but the question is asking for the side product, not the original alcohol

Si will bond with 4 substituents. If it's in an acidic solution, you have to think protonation of oxygen. Only one of the answers meets those two requirements.