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Sample Problems for for exam #2.
1. Draw the Major organic product for the reactions below. Label if they go by an Sn1 or
Sn2 type mechanism. Also, rank the Sn1 type reactions in order of reactivity (fastest to
slowest).
CH3CH2OH
Cl
H3C
OH
HCl conc
CH3
OH
HBr conc
HBr conc
OH
OH
HCl conc
CH2CH3
2. In the reactions above, the alcohols reacted readily with concentrated HBr . Why will
the same reactions above not work when using NaBr instead of HBr (since both these
reagents contain Br- as a nucleophile one would suspect that they both would be
effective)
3. Draw the full mechanism for the reactions shown below.
HCl conc.
OH
Cl
HBr conc
Br
OH
OH
SOCl2
Cl
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