C201HPT3F07 - CHM 201 Organic Chemistry I Exam 3 Key...

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1 CHM 201- Organic Chemistry I Exam 3 Key. Answers on last page. 1. An S N 2 reaction proceeds in the direction that allows the stronger base to displace the weaker base. For the equilibrium shown below, which side predominates at equilibrium? CH 3 CH 2 Cl + Br - CH 3 CH 2 Br + Cl - a. product (right) side b. reactant (left) side c. neither 2. For each of the following pairs of S N 2 reactions, indicate which reaction occurs faster. Comparison I: (CH 3 ) 2 CHCH 2 CH 2 Br + OH - or CH 3 CH 2 CHBr + OH - | CH 3 Comparison II: CH 3 CH 2 Cl + CH 3 O - or CH 3 CH 2 Cl + CH 3 S - (in ethanol) a. I: left reaction II: left reaction b. I: right reaction II: left reaction c. I: left reaction II: right reaction d. I: right reaction II: right reaction 3. The following represents: a) the rate-determining step of an S N 2 reaction b) the rate-determining step of an S N 1 reaction c) a fast step of an S N 1 reaction d) the transition state of the rate-determining step of an E1 reaction e) the intermediate in an E2 reaction 4. Under a certain set of experimental conditions, the reaction of pure (R)-2-bromobutane with water molecules proceeds exclusively by an S N 1 reaction, with no trace of an S N 2 reaction. Under these conditions, the reaction produces a mixture of 55% (S)-2-butanol and 45% (R)-2-butanol. The best explanation for this is: a) the solvent can stabilize the intermediate carbocation b) the entering nucleophile can attack the planar carbocation from either face with equal probability
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