chapter 16 (wade)

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1. 1) Which of the following is an incorrect description of C 8. 16) What is the major difference between an E
benzene? antiaromatic and aromatic compound?
A) The CCC bond angles are all equal to 120°. A) The structure must be cyclic for aromatic but not
B) The molecule is planar. antiaromatic compounds?
C) The molecule is a 6-membered ring which contains B) Antiaromatic compounds have at least one sp3
alternating single and double carbon-carbon bonds. hybridized atom in the ring
D) The molecule is aromatic. C) Antiaromatic compounds can assume a chair-like
E) The molecule can be drawn as a resonance hybrid of structure while aromatic compounds are nearly flat
two Kekule structures. D) Aromatic compounds cannot have a charged atom in
the structure
2. 3) What is the bond order of the carbon-carbon bonds C
E) Only aromatic compounds follow Huckle's rule.
in benzene?
A) 0.5 9. 22) Aromatic molecules contain ________ π electrons. C
B) 1 A) no
C) 1.5 B) 4n + 1 (with n an integer)
D) 2 C) 4n + 2 (with n an integer)
E) 3 D) 4n (with n an integer)
E) unpaired
3. 7) In the molecular orbital representation of benzene, D
how many π molecular orbitals are present? 10. 23) Which of the following is another name for B
A) 1 cyclobutadiene?
B) 2 A) [2]annulene
C) 4 B) [4]annulene
D) 6 C) [6]annulene
E) 8 D) Dewar benzene
E) antibenzene
4. 8) Which of the following undergoes SN2 reaction with A
sodium methoxide most rapidly? 11. 35) Which of the following is the same as the tropylium A
A) PhCH2Br ion?
B) Ph3CBr A) cycloheptatrienyl cation
C) PhCH2CH2Br B) cycloheptatrienyl anion
D) PhBr C) cyclopentadienyl cation
E) PhCH2CH2CH2Br D) cyclopentadienyl anion
E) cyclopropenyl anion
5. 9) Which of the following undergoes solvolysis in B
methanol most rapidly? 12. 57) Nitrogen's lone pair electrons occupy what type of C
A) PhCH2Br orbital in pyridine?
B) Ph3CBr A) s
C) PhCH2CH2Br B) sp
D) PhBr C) sp2
E) PhCH2CH2CH2Br D) sp3
E) p
6. 10) How many distinct nodal planes which are C
perpendicular to the molecular plane are present in the 13. 79) Which of the following is not a fused-ring B
π4* orbital of benzene? heterocycle?
A) 0 A) purine
B) 1 B) pyrimidine
C) 2 C) benzofuran
D) 4 D) indole
E) 5 E) quinoline
7. 11) How many pairs of degenerate π molecular orbitals E 14. 86) How many distinct trichlorobenzene isomers are B
are found in benzene? possible?
A) 6 A) 2
B) 5 B) 3
C) 4 C) 4
D) 3 D) 5
E) 2 E) 6
15. 87) Which of the following is another accepted name C 22. 117) In the carbon NMR, in what region of the spectrum D
for methyl phenyl ketone? does one typically observe carbons which are part of
A) anisole the aromatic ring?
B) cresol A) -10-0 ppm
C) acetophenone B) 40-60 ppm
D) benzophenone C) 80-100 ppm
E) cresone D) 120-150 ppm
E) 200-220 ppm
16. 88) Which of the following is also an acceptable name B
for 3-nitrophenol? 23. 118) Which of the following compounds has the most B
A) o-nitrophenol signals in the proton-decoupled 13C NMR spectrum?
B) m-nitrophenol A) o-dibromobenzene
C) p-nitrophenol B) m-dibromobenzene
D) 3-cresol C) p-dibromobenzene
E) hydroquinone D) 1,3,5-tribromobenzene
E) 1,2,3,4-tetrabromobenzene
17. 92) Which of the following is also an acceptable name B
for 1,3,5-trimethylbenzene? 24. 119) In the mass spectrum of isobutylbenzene, the base E
A) styrene peak occurs at m/z ________.
B) mesitylene A) 134
C) cumene B) 133
D) cymene C) 119
E) 1,3,5-xylene D) 105
E) 91
18. 113) Which of the following compounds has the lowest C
boiling point? 25. 120) How many peaks are in the proton spin decoupled A
A) 1,2,3-trichlorobenzene 13C NMR spectrum of p-dichlorobenzene?
B) 1,2,4-trichlorobenzene A) 2
C) p-dichlorobenzene B) 3
D) m-dichlorobenzene C) 4
E) o-dichlorobenzene D) 5
E) 6
19. 114) Which of the following compound has the highest E
melting point? 26. 121) How many peaks are in the proton spin decoupled B
A) benzene 13C NMR spectrum of 1,3,5-trinitrobenzene?
B) toluene A) 1
C) o-dichlorobenzene B) 2
D) m-dichlorobenzene C) 3
E) p-dichlorobenzene D) 4
E) 6
20. 115) In the UV-visible spectra of the following B
compounds, in which does lambda max appear at the 27. 122) How many peaks are in the proton spin decoupled D
highest wavelength? 13C NMR spectrum of 1,2,3-trichlorobenzene?
A) 3-phenylpropene A) 1
B) 1-phenylpropene B) 2
C) benzene C) 3
D) n-octylbenzene D) 4
E) isopropylbenzene E) 6
21. 116) In the proton NMR, in what region of the spectrum D
does one typically observe hydrogens bound to the
aromatic ring?
A) 1.0-1.5 ppm
B) 2.0-3.0 ppm
C) 4.5-5.5 ppm
D) 7.0-8.0 ppm
E) 9.0-10.0 ppm