20. Select the set of reagents/conditions that will most likely afford the following organic transformation: a. NaOEt, heat b. HCI, peroxide c. KOtBu, heat d. ELOH, heat

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20. Select the set of reagents/conditions that will most likely afford the following
organic transformation:
a. NaOEt, heat
b. HCl, peroxide
c. KOtBu, heat
d. EtOH, heat
21. Select the proper reaction sequence to convert benzene to 3-butyl-1-
bromobenzene in a reasonable yield.
a. 1. Brz/FeBr3; 2. butanoyl chloride/AlCl3; 3. Hg(Zn), HCl(aq)
b. 1. Butanoyl chloride/AlCl3; 2. Brz/FeBr3; Hg(Zn), HCl(aq)
c. 1. HNO3/H2SO4 (aq); 2. butanoyl chloride/AlCl3; 3. HBr(aq)/heat
d. 1. Butanoyl chloride/AIC13; 2. HNO3/H2SO4(aq); 3. HBr(aq)/heat
С.
22. Consider the following nucleophilic acyl substitution reaction. Which of the
following statements most accurately reflects the mechanism?
HO
onblo
a. overall exergonic reaction; nucleophilic attack followed by loss of leaving
group; loss of leaving group step is rate-limiting
b. overall exergonic reaction; nucleophilic attack followed by loss of leaving
group; nucleophilic attack is rate limiting
c. overall endergonic reaction; nucleophilic attack followed by loss of leaving
group; loss of leaving group is rate limiting
d. neither exergonic nor endergonic reaction; nucleophilic attack followed by
loss of leaving group; nucleophilic attack is rate limiting.
23. If the chemical shift (8) for a proton is 9.124 ppm in a 40 MHz NMR
spectrometer, then the chemical shift for the same proton in an 800 MHz
NMR spectrometer would be:
а. 3.637
b. 7.272
C. 9.124
d. 10.982
Transcribed Image Text:20. Select the set of reagents/conditions that will most likely afford the following organic transformation: a. NaOEt, heat b. HCl, peroxide c. KOtBu, heat d. EtOH, heat 21. Select the proper reaction sequence to convert benzene to 3-butyl-1- bromobenzene in a reasonable yield. a. 1. Brz/FeBr3; 2. butanoyl chloride/AlCl3; 3. Hg(Zn), HCl(aq) b. 1. Butanoyl chloride/AlCl3; 2. Brz/FeBr3; Hg(Zn), HCl(aq) c. 1. HNO3/H2SO4 (aq); 2. butanoyl chloride/AlCl3; 3. HBr(aq)/heat d. 1. Butanoyl chloride/AIC13; 2. HNO3/H2SO4(aq); 3. HBr(aq)/heat С. 22. Consider the following nucleophilic acyl substitution reaction. Which of the following statements most accurately reflects the mechanism? HO onblo a. overall exergonic reaction; nucleophilic attack followed by loss of leaving group; loss of leaving group step is rate-limiting b. overall exergonic reaction; nucleophilic attack followed by loss of leaving group; nucleophilic attack is rate limiting c. overall endergonic reaction; nucleophilic attack followed by loss of leaving group; loss of leaving group is rate limiting d. neither exergonic nor endergonic reaction; nucleophilic attack followed by loss of leaving group; nucleophilic attack is rate limiting. 23. If the chemical shift (8) for a proton is 9.124 ppm in a 40 MHz NMR spectrometer, then the chemical shift for the same proton in an 800 MHz NMR spectrometer would be: а. 3.637 b. 7.272 C. 9.124 d. 10.982
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