AAMC 7 ochem q

[chiddler]

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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[MedPR]

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

 

[chiddler]

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

oh...

 

[MedPR]

oh...

FWIW, I had a 50-50 between methanol and t-butanol and I guessed wrong as well.

 

[chiddler]

FWIW, I had a 50-50 between methanol and t-butanol and I guessed wrong as well.

Schadenfreude.

 

[osprey099]

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.

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