AAMC 7 ochem q

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chiddler

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10+ Year Member
Which alcohol + concentrated HCl reacts the fastest?

A. Isopropyl alcohol
B. Methanol
C. sec-butanol
D. t-butanol

Answer is D.

I don't understand why t-butanol, going via SN1, is faster than methanol's SN2. Would appreciate help.

thanks.
 
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Concentrated HCl implies SN1 due to aqueous (protic) solvent. There was a thread about this a few weeks ago and in it someone mentioned that the SN2 equivalent is typically carried out with SOCl2
 
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chiddler said:
Which alcohol + concentrated HCl reacts the fastest?

A. Isopropyl alcohol
B. Methanol
C. sec-butanol
D. t-butanol

Answer is D.

I don't understand why t-butanol, going via SN1, is faster than methanol's SN2. Would appreciate help.

thanks.
Click to expand...

Concentrated HCl means the reaction is in polar protic environment, which favors SN1
 
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