Review For Test 1 - Ch12-15-. F17. Stafford

CHEM 2425. Review for test 1 (ch12-15). F17.
Stafford
Multiple Choice
Identify the choice that best completes the statement or answers the question.
____ 1. What range of wavelengths corresponds to the infrared region of the electromagnetic spectrum?
a. 200-400 nm
b. 400-700 nm
c. 2.5-50 m
d. 2-10 mm
____ 2. Which of the following bonds (circled) vibrates at the highest frequency?
a. 1
b. 2
c. 3
d. 4
____ 3. Which of the following combinations of peaks appears in the 1H NMR spectrum of diethyl ether,
CH3CH2OCH2CH3?
a. a triplet and a doublet
b. a quartet and a sextet
c. two singlets
d. a triplet and a quartet
____ 4. Which C4H9Br compound gives a triplet at approximately 3.5 ppm in the 1H NMR spectrum?
a. 1
b. 2
c. 3
d. 4
____ 5. What is the relative area of the six peaks in a sexet in an 1H NMR spectrum?
a. 1:2:3:3:2:1
b. 1:3:6:6:3:1
c. 1:5:10:10:5:1
d. 1:6:15:15:6:1
____ 6. Which of the following compounds have enantiotopic protons?
1 2425. Review for test 1 (ch12-15). F17. Stafford

1. propane
2. butane
3. 2-methylpropane
a. only 1
b. only 2
c. only 1 and 2
d. 1, 2 and 3
____ 7. Which of the following is true for pair of homotropic protons?
1. They will appear at the same chemical shift in an achiral (i.e., nonchiral) environment
2. They will appear at the same chemical shifts in a chiral environment
a. only 1
b. only 2
c. neither 1 nor 2
d. both 1 and 2
____ 8. Which C9H10O compound gives the following 1H NMR spectrum?

a. 1
b. 2
c. 3
d. 4
____ 9. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 60?
a. 1-hexanol
b. 2-hexanol
c. hexanal
d. hexanoic acid
____ 10. Which of the following arrangements of p atomic orbitals of 1,3-butadiene has the greatest number of nodes?
a. 1
b. 2
c. 3
d. 4
____ 11. What is (are) the major organic product(s) formed in the following reaction?
a. only 1
b. only 1 and 3
c. only 2 and 4
d. only 1 and 4
____ 12. Which of the following is(are) formed upon addition of 1 mol of Br2 to 1,3-cyclohexane?

a. only 2
b. only 1 and 3
c. only 2 and 4
d. 1, 2 and 3
____ 13. What is (are) the major organic product(s) formed in the following reaction?
a. only 1
b. only 3
c. only 1 and 3
d. only 2 and 4
____ 14. What are the units of  in ultraviolet-visible spectroscopy?

a. M1cm1
b. Mcm
c. Jmol1M1
d. none,  is a dimensionless quantity
____ 15. Which of the following laws relates absorbance to the concentration of a sample and the pathlength in
ultraviolet-visible spectroscopy?
a. Buzz-Beer law
b. Beer-Lambert law
c. Duff-Beer law
d. Christopher-Lambert law
____ 16. What is the IUPAC name of the following compound?

a. 2,4-dibromotoluene
b. 2,4-dibromophenol
c. 2,4-dibromohydroxybenzene
d. 4,6-dibromophenol
____ 17. Which of the following represents the energy levels of the molecular orbitals of benzene?
a. 1
b. 2
c. 3
d. 4
____ 18. What is the correct assignment of the names of the following heterocycles?
a. 1 = pyrrole; 2 = thiophene; 3 = pyridine

b. 1 = thiophene; 2 = furan; 3 = pyrrole
c. 1 = pyridine; 2 = thiophene; 3 = furan
d. 1 = pyridine; 2 = thiophene; 3 = pyrrole

____ 19. What is the hybridization of the nitrogen atom of pyridine?
a. s
b. sp
c. sp2
d. sp3
____ 20. Which of the following compounds is antiaromatic?
a. ethane
b. cyclobutadiene
c. benzene
d. cyclooctatetraene
____ 21. Which of the following compounds undergoes heterolytic carbon-halogen bond cleavage to form a stable
organic cation?
a. 1
b. 2
c. 3
d. 4
____ 22. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more
acidic > less acidic)?
a. 1>2>3
b. 2>3>1
c. 3>2>1
d. 1>3>2
____ 23. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
____ 24. What is the major organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4
____ 25. Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene?

a. 1
b. 2
c. 3
d. 4
____ 26. What are the relative positions of the substituents in the following structure?
a. anti
b. meta
c. ortho
d. para
____ 27. What are the relative positions of the substituents in the following structure?

a. anti
b. meta
c. ortho
d. para
____ 28. Which of the following is true about [10]annulene?
a. [10]annulene is planar
b. [10]annulene is nonaromatic
c. [10]annulene undergoes addition reactions similar to simple alkenes
d. [10]annulene has 10 pi electrons
____ 29. Which of the following is not true about [the bridged [10]annulene shown below?
a. all of the carbon atoms of bridged [10]annulene are all in the same plane
b. bridged [10]annulene is aromatic
c. bridged [10]annulene undergoes substitution reactions similar to benzene
d. bridged [10]annulene has 10 pi electrons
____ 30. Which of the following does not undergo oxidation in the presence of H2CrO4?
a. 1
b. 2
c. 3
d. 4
Completion
Complete each statement.

MATCH each of the following groups of bond-types to the region of the infrared spectrum in which their
absorptions occur. Place the letter of the region in the blank to the left of the bond-type.
a. 4000 to 2500 cm1

b. 2500 to 2000 cm1
c. 2000 to 1500 cm1
d. below 1500 cm1
1. _____ CC, CO, CN, and CX single-bond vibrations.
2. _____ C=O, C=N, and C=C bond absorptions.
3. _____ NH, CH, and OH stretching and bending motions.
4. _____ triple bond stretching vibrations.
MATCH a structure from the list below to the following IR spectra. Place the letter of the structure in the
blank provided.
5. _____

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/
6. _____
7. _____

MATCH each of the following molecules to the region of the infrared spectrum in which they may show a
significant absorption. Place the letter of the region in the blank to the left of the bond-type.
a. 4000 to 2500 cm1

b. 2500 to 2000 cm1
c. 2000 to 1500 cm1
d. below 1500 cm1
8. _______
9. _______
CH3CH2OCH(CH3)
10. _______
For each of the compounds below tell how many signals you would expect the molecule to have in its normal,
broadband hydrogen-decoupled 13C NMR spectra. Enter the numerical value in the blank provided to the
left of the structure.
11. _______

12. _______
13. _______
14. _______
15. _______
Predict the splitting of each of the numbered hydrogen atoms in the structure below in a 1H NMR spectrum.
Identify as singlet, doublet, triplet, quartet, quintet, sextet, septet, .... Place the correct splitting in the blank
to the left of the number.
16. ______ 1
17. ______ 1
18. ______ 1
19. Identify the ratio of peak areas upon integration of the 1H NMR spectrum for A, B, and C respectively.
Enter the numbers separated by colons.

Consider the following structure. Answer the following questions by placing the appropriate number in the
blank to the left.
20. _____The number of nonequivalent hydrogen atoms in this compound.
21. _____The number of signals in the hydrogen-decoupled 13C NMR of this compound.
22. _____The number of nonsinglet splitting patterns in the 1H NMR of this compound.
The following question(s) refer to the mass spectrum shown below.
23. The base peak in this spectrum occurs at a m/z of ______.

24. This compound contains C, H, and one other atom. The other atom from the mass spectrum is __________.
Refer to the mass spectrum of 2-methylbutane shown below to answer the following question(s).
25. The peak at a m/z of _____ represents M+.
26. The peak at a m/z of _____ represents the base peak.
27. The peak at a m/z of _____ represents the following species.

+CH2CH3
30. The mass of the larger charged fragment produced by the dehydration of the following compound occurs at a
m/z of _______.

31. Cyclohexene and hex-2-yne both have the molecular formula, C6H10. The mass spectrum below belongs
to ___________________.
32. Alpha cleavage of the following compound will produce a peak at a m/z of _______.
33. Dehydration of the following compound will produce a peak at a m/z of _______.
Consider the reaction below to answer the following question(s):
Enter the appropriate letter in the blank for each the following statements.

34. The nucleophile in this reaction is ____.
35. The electrophile in this reaction is ____.
36. The kinetically controlled product in this reaction is _____.
37. The product that results from 1,4-addition is _____.
38. The product that results from following mechanistic step is _____.
39. Consider the following spectrum for a conjugated diene.
If a similar spectrum were taken for a conjugated tetraene, the max would be _________than 217 nm.
40. Based on the following table.

Compound max (nm)
W 190
X 340
Y 560
Z 250
Compound ______ has the largest energy difference between the HOMO and LUMO.
Consider the reaction below to answer the following question(s).

Fill in the blank in the question with the appropriate letter.
41. The dienophile in the reaction is ____.
42. The diene in the reaction is ____.
43. This is an example of a(n) ____________ reaction.

A. sigmatropic reaction
B. electrophillic addition
C. Diels-Alder reaction
D. Cope rearrangement
Answer the following questions concerning sulfathiazole below by filling ieach blank with the appropriate
response.
44. The hybridization of the nitrogen atom in sulfathiazole is ______.

A. sp
B. sp2
C. sp3
45. Assuming that the sulfur atom is sp2-hybridized, there are _____ -electrons in the sulfathiazole ring.
46. According to Hückel criteria, sulfathiazole is predicted to be ___________.
Consider the cycloheptatrienyl anion. Complete the following questions by filling in the blank with the
appropriate word.
47. According the Hückel criteria this anion would be classified as ______________.
48. This anion has______  electrons.
49. Consider the following two compounds.

A
B
An ether solution containing these two substances was mixed with an aqueous 1 M NaOH solution.
Substance _____ will be found in the basic layer.
50. Consider the following compound.
When treated with acidic K2Cr2O7 the product would be classified as a ___________.
Consider the following structure.
51. If named as an annulene, the name would be [ __ ] annulene.
52. This structure contains ____  electrons.
53. Using the Hückel criteria, the compound would be ______________.
Consider the following structure.
The 1H NMR spectrum of [14]annulene at 60C shows two peaks, one at 0 ppm and one at 7.6 ppm.
54. The NMR data would seem to indicate that this compound is ____________.
55. The ratio of peak areas, respectively for the 7.6 ppm and 0 ppm, peaks would be_______.

Matching
The following questions pertain to the display of NMR spectra. Match a term to each description below.
a. TMS
b. high-field or upfield side
c. MHz
d. delta ()
e. low-field or downfield side
f. chemical shift
g. intensity
____ 1. When looking at a NMR spectrum the right-hand part of the chart is the _____.
____ 2. The exact place on the spectrum at which a nucleus absorbs is called its _____.
____ 3. The calibration standard for 1H and 13C NMR is _____.
____ 4. NMR spectrum are calibrated using an arbitrary scale that is divided into _____ units.
____ 5. The vertical axis of spectrum displays the _____ of the signal.
Problem
1. Provide the structure of three compounds with the molecular formula C4H8O that give an absorption peak at
1600-1640 cm-1 in the infrared spectrum, but no significant peaks at 3000-3600 cm-1 or at 1650-1750 cm-1.
2. Provide the structure of four compounds with the molecular formula C5H10O which give a strong absorption
peak at 1700-1740 cm-1 in the infrared spectrum, but no significant peaks at 1600-1640 cm-1 .
3. Provide a brief explanation to account for the observation that 1-butyne gives a significantly stronger peak at
~1250 cm-1 in the infrared spectrum than 2-butyne..
4. Provide a brief explanation to account for the observation that the frequency of the C=O stretching absorption
in the infrared spectrum of 2-butanone is higher than that of 3-buten-2-one.
5. Provide a brief explanation to account for the observation that the frequency of the C=O stretching absorption
in the infrared spectrum of N,N-dimethylacetamide, CH3CON(CH3)2, is higher than that of methyl acetate,
CH3CO2CH3.
6. How could you distinguish between 1-hexyne and 2-hexyne by infrared spectroscopy?
7. How could you distinguish between 1-butanol and diethyl ether by infrared spectroscopy?

8. How could you distinguish between methyl butanoate and pentanoic acid by infrared spectroscopy?
9. Label three peaks in the following spectrum with the bond that gives rise to them, and identify the functional
group that is present in the compound (the compound has a formula of C6H14O)?
group that is present in the compound (the compound has a formula of C5H10O2)?
group that is present in the compound (the compound has a formula of C4H9NO)?

12. Identify the compound (C4H6O2) that gives the following 1H NMR spectrum.
14. Identify the compound (C3H7Cl) that gives the following 1H NMR spectrum.

15. Identify the compound (C3H7Cl) that gives the following 1H NMR spectrum.
16. Identify the compound (C4H8O) that gives the following 1H NMR spectrum.
17. Identify the compound (C4H8O) that gives the following 1H NMR spectrum.

19. Identify the compound (C8H11N) that gives the following 1H NMR spectrum.
20. Identify the compound (C8H10) that gives the following 1H NMR spectrum.

23. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum
with m/z of 97 and an M+1 peak that is 6.6% of the intensity of the molecular ion peak?

24. What is the most likely molecular formula of a compound (that contains only C, H and O) which has a
molecular ion in the EI mass spectrum with m/z of 104 and an M+1 peak that is 5.5% of the intensity of the
molecular ion peak?
with m/z of 136, with a M+1 and M+2 peaks that are 4.4% and 49% of the intensity of the molecular ion peak,
respectively.
with m/z of 120, with a M+1 and M+2 peaks that are 6.6% and 24% of the intensity of the molecular ion peak,
respectively.
27. Provide the mass of the three most prominent fragment peaks that are observed in the EI mass spectrum of
2-hexanone, CH3CH2CH2CH2COCH3 (molecular ion m/z = 100) and describe the processes that lead to each
of these fragments.
28. Provide the mass of the three most prominent fragment peaks that are observed in the EI mass spectrum of
methyl pentanoate, CH3CH2CH2CH2CO2CH3 (molecular ion m/z = 116) and describe the processes that lead
to each of these fragments.
29. Which C5H12O compound give the following EI mass spectrum?
30. Which C5H12O compound give the following EI mass spectrum?

31. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant
fragment peaks at m/z 85, 58, 57, 43 and 42 in the EI mass spectrum?
32. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant
fragment peaks at m/z 71, 58, 57, 43 and 29 in the EI mass spectrum?
33. What is the IUPAC name of the following compound?
35. What are the two major organic products obtained from the following reaction?
37. Provide the structures of the constitutional isomers of the two major organic products obtained from the
following reaction?
38. What is the major organic product obtained from the following reaction?
39. Draw two resonance structures of the reactive intermediate that accounts for the formation of 1,2- and
1,4-addition products upon reaction of 1,3-butadiene with one equivalent of bromine.

40. Draw two resonance structures of the reactive intermediate that accounts for the formation of 1,2- and
1,4-addition products upon reaction of 1,3-butadiene with one equivalent of HBr.
41. How would you be able to distinguish between 1,3-cyclohexadiene and 1,4-cyclohexadiene using ultraviolet
spectroscopy?
42. Which of 1,3-cyclohexadiene and 1,4-cyclohexadiene has the greatest heat of hydrogenation (i.e., the most
exothermic reaction with H2 in the presence of a catalyst). Provide a brief explanation for your choice ?

51. List all of the requirements of a molecule for it to be considered aromatic.

52. Provide a brief explanation of why furan (below) is aromatic. Your answer should identify the hybridization
of the oxygen atom and account for which electrons are in the pi system.
53. Provide a brief explanation of why the cyclopentadienyl anion (below) is aromatic. Your answer should
identify the hybridization of each carbon atom and account for which electrons are in the pi system.

2425. Review for test 1 (ch12-15). F17. Stafford
Answer Section
MULTIPLE CHOICE
1. ANS: C PTS: 1
2. ANS: D PTS: 1
3. ANS: D PTS: 1
4. ANS: A PTS: 1
5. ANS: C PTS: 1
6. ANS: B PTS: 1
7. ANS: D PTS: 1
8. ANS: B PTS: 1
9. ANS: D PTS: 1
10. ANS: C PTS: 1
11. ANS: D PTS: 1
12. ANS: C PTS: 1
13. ANS: B PTS: 1
14. ANS: A PTS: 1
15. ANS: B PTS: 1
16. ANS: B PTS: 1
17. ANS: C PTS: 1
18. ANS: C PTS: 1
19. ANS: C PTS: 1
20. ANS: B PTS: 1
21. ANS: D PTS: 1
22. ANS: B PTS: 1
23. ANS: C PTS: 1
24. ANS: A PTS: 1
25. ANS: A PTS: 1
26. ANS: C PTS: 1
27. ANS: D PTS: 1
28. ANS: A PTS: 1
29. ANS: A PTS: 1
30. ANS: D PTS: 1
COMPLETION
1. ANS: d
PTS: 1
2. ANS: c
PTS: 1

3. ANS: a
PTS: 1
4. ANS: b
PTS: 1
5. ANS: F
PTS: 1
6. ANS: D
PTS: 1
7. ANS: A
PTS: 1
8. ANS: b
PTS: 1
9. ANS: d
PTS: 1
10. ANS: a
PTS: 1
11. ANS:
3
three
PTS: 1
12. ANS:
5
five
PTS: 1
13. ANS:
6
six
PTS: 1
14. ANS:
5
five
PTS: 1
15. ANS:
5
five

PTS: 1
16. ANS: singlet
PTS: 1
17. ANS: quartet
PTS: 1
18. ANS: triplet
PTS: 1
19. ANS: 3:1:6
PTS: 1
20. ANS:
3
three
PTS: 1
21. ANS:
3
three
PTS: 1
22. ANS:
0
zero
PTS: 1
23. ANS: 77
PTS: 1
24. ANS:
Br
bromine
Bromine
PTS: 1
25. ANS: 72
PTS: 1
26. ANS: 43
PTS: 1
27. ANS: 57
PTS: 1
28. ANS: 43

PTS: 1
29. ANS: 29
PTS: 1
30. ANS: 126
PTS: 1
31. ANS:
cyclohexene
Cyclohexene
PTS: 1
32. ANS: 31
PTS: 1
33. ANS: 82
PTS: 1
34. ANS: A
PTS: 1
35. ANS: B
PTS: 1
36. ANS: D
PTS: 1
37. ANS: C
PTS: 1
38. ANS: D
PTS: 1
39. ANS:
greater
longer
PTS: 1
40. ANS: W
PTS: 1
41. ANS: B
PTS: 1
42. ANS: A
PTS: 1

43. ANS: C
PTS: 1
44. ANS: B
PTS: 1
45. ANS:
six
6
PTS: 1
46. ANS: aromatic
PTS: 1
47. ANS: antiaromatic
PTS: 1
48. ANS:
8
eight
PTS: 1
49. ANS: B
PTS: 1
50. ANS: quinone
PTS: 1
51. ANS: 16
PTS: 1
52. ANS: 16
PTS: 1
53. ANS: antiaromatic
PTS: 1
54. ANS: aromatic
PTS: 1
55. ANS:
5:2
5 to 2
5/2
PTS: 1

MATCHING
1. ANS: B PTS: 1
2. ANS: F PTS: 1
3. ANS: A PTS: 1
4. ANS: D PTS: 1
5. ANS: G PTS: 1
PROBLEM
1. ANS:
Any three of the following:
PTS: 1
2. ANS:
Any four of the following:
PTS: 1
3. ANS:
2-Butyne is a symmetrical molecule and stretching of the triple bond does not give rise to a change in the
bond dipole moment.
PTS: 1
4. ANS:
The C=O bond of 3-buten-2-one is weaker in 2-butanone by virtue of the existence of an additional
resonance structure with a C–O single bond.

PTS: 1
5. ANS:
The C=O bond of the amide is weaker than that of the ester. Nitrogen is less electronegative than oxygen, and
therefore a better electron pair donor. Accordingly, the resonance contributor in which the nitrogen has
donated a pair of electrons to the carbonyl carbon atom is an important contributor to the structure.
PTS: 1
6. ANS:
1-Hexyne, a terminal alkyne, has a stronger peak for the CC stretching vibration than 2-hexyne, an internal
alkynes.
PTS: 1
7. ANS:
The infrared spectrum of 1-butanol has a strong and broad peak at 3500-3000 cm-1 for the O–H bond. This
peak is absent in the spectrum of ethers.
PTS: 1
8. ANS:
The infrared spectrum of pentanoic acid has a very broad peak at 3300-2500 cm-1 for the O–H bond. This
peak is absent in the spectrum of esters.
PTS: 1
9. ANS:
O-H: ~3300 cm-1
C-H: ~2900 cm-1
C-O: ~1060 cm-1
Functional group: alcohol
PTS: 1

10. ANS:
O-H: 3000-3600 cm-1
C-H: ~2900 cm-1
C-O: ~1700 cm-1
Functional group: carboxylic acid
PTS: 1
11. ANS:
N-H: ~3500 cm-1
C-H: ~2900 cm-1
C=O: ~1680 cm-1
Functional group: amide
PTS: 1
12. ANS:
methyl propionate, CH3CH2CO2CH3
PTS: 1
13. ANS:
ethyl acetate, CH3CO2CH2CH3
PTS: 1
14. ANS:
2-chloropropane
PTS: 1
15. ANS:
1-chloropropane
PTS: 1
16. ANS:
butanal
PTS: 1
17. ANS:
2-butanone
PTS: 1
18. ANS:
3-phenylpropanoic acid, PhCH2CH2CO2H
PTS: 1
19. ANS:
1-phenylethanamine, PhCH(NH2)CH3
PTS: 1

20. ANS:
p-xylene (1,4-dimethylbenzene)
PTS: 1
21. ANS:
m-xylene (1,3-dimethylbenzene)
PTS: 1
22. ANS:
o-xylene (1,2-dimethylbenzene)
PTS: 1
23. ANS:
C6H11N
PTS: 1
24. ANS:
C5H12O2
PTS: 1
25. ANS:
C4H9Br
PTS: 1
26. ANS:
C6H13Cl
PTS: 1
27. ANS:
85: loss of CH3• (15) by -cleavage
72: loss of CH2=CH2 (28) by McLaferty rearrangement
43: loss of C4H9• (57) by -cleavage
PTS: 1
28. ANS:
88: loss of CH2=CH2 (28) by McLaferty rearrangement
85: loss of CH3O• (31) by -cleavage
59: loss of C4H9• (57) by -cleavage
PTS: 1
29. ANS:
2-pentanol
PTS: 1
30. ANS:
2-methyl-2-butanol
PTS: 1
31. ANS:
4-methyl-2-pentanone
PTS: 1
32. ANS:
2-methylpentanal
PTS: 1
33. ANS:
(E)-2,3-dimethyl-2,4-hexadiene
PTS: 1
34. ANS:
(E)-2,3-dimethyl-1,3-pentadiene
PTS: 1
35. ANS:
PTS: 1
36. ANS:
PTS: 1
37. ANS:
PTS: 1
38. ANS:
PTS: 1
39. ANS:

PTS: 1
40. ANS:
PTS: 1
41. ANS:
1,3-Cyclohexadiene, in which the two pi-bonds are conjugated, absorbs at a higher wavelength than
1,4-cyclohexadiene.
PTS: 1
42. ANS:
1,4-Cyclohexadiene has a greater heat of hydrogenation. This is because 1,3-cyclohexadiene is stabilized by
conjugation of the two pi bonds.
PTS: 1
43. ANS:
3-bromo-4-nitrophenol
PTS: 1
44. ANS:
4-chloro-3-nitrobenzoic acid
PTS: 1
45. ANS:
3,4-dichloroaniline
PTS: 1
46. ANS:
4-bromo-2-propylbenzonitrile
PTS: 1
47. ANS:

PTS: 1
48. ANS:
PTS: 1
49. ANS:
PTS: 1
50. ANS:
PTS: 1
51. ANS:
An aromatic molecule has an uninterrupted cycle of overlapping p orbitals (i.e., the cyclic structure should be
planar) that contains 2n+2 (i.e., 2, 6, 8, ...) electrons
PTS: 1
52. ANS:
The oxygen is sp2 hybridized. One lone pair is in a p orbital and is part of the pi system, along with one
electron in the p orbital on each of the four carbon atoms. The other lone pair of the oxygen is in an sp2 orbital,
which is in the plane of the ring and not involved in the pi system.
PTS: 1

53. ANS:
The all five carbons are sp2 hybridized. The lone pair is in a p orbital and is part of the pi system, along with
one electron in the p orbital on each of the other four carbon atoms for a total of six pi electrons.
PTS: 1

Review For Test 1 - Ch12-15-. F17. Stafford

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CHEM 2425. Review for test 1 (ch12-15). F17.

1 2425. Review for test 1 (ch12-15). F17. Stafford

2 2425. Review for test 1 (ch12-15). F17. Stafford

3 2425. Review for test 1 (ch12-15). F17. Stafford

____ 14. What are the units of  in ultraviolet-visible spectroscopy?

4 2425. Review for test 1 (ch12-15). F17. Stafford

a. 1 = pyrrole; 2 = thiophene; 3 = pyridine

5 2425. Review for test 1 (ch12-15). F17. Stafford

6 2425. Review for test 1 (ch12-15). F17. Stafford

7 2425. Review for test 1 (ch12-15). F17. Stafford

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9 2425. Review for test 1 (ch12-15). F17. Stafford

a. 4000 to 2500 cm1

1. _____ CC, CO, CN, and CX single-bond vibrations.

2. _____ C=O, C=N, and C=C bond absorptions.

3. _____ NH, CH, and OH stretching and bending motions.

4. _____ triple bond stretching vibrations.

10 2425. Review for test 1 (ch12-15). F17. Stafford

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/

11 2425. Review for test 1 (ch12-15). F17. Stafford

a. 4000 to 2500 cm1

12 2425. Review for test 1 (ch12-15). F17. Stafford

13 2425. Review for test 1 (ch12-15). F17. Stafford

20. _____The number of nonequivalent hydrogen atoms in this compound.

The following question(s) refer to the mass spectrum shown below.

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/

23. The base peak in this spectrum occurs at a m/z of ______.

14 2425. Review for test 1 (ch12-15). F17. Stafford

Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/

25. The peak at a m/z of _____ represents M+.

26. The peak at a m/z of _____ represents the base peak.

27. The peak at a m/z of _____ represents the following species.

28. The peak at a m/z of _____ represents the following species.

29. The peak at a m/z of _____ represents the following species.

15 2425. Review for test 1 (ch12-15). F17. Stafford

Consider the reaction below to answer the following question(s):

16 2425. Review for test 1 (ch12-15). F17. Stafford

35. The electrophile in this reaction is ____.

36. The kinetically controlled product in this reaction is _____.

37. The product that results from 1,4-addition is _____.

39. Consider the following spectrum for a conjugated diene.

40. Based on the following table.

Consider the reaction below to answer the following question(s).

17 2425. Review for test 1 (ch12-15). F17. Stafford

41. The dienophile in the reaction is ____.

42. The diene in the reaction is ____.

43. This is an example of a(n) ____________ reaction.

44. The hybridization of the nitrogen atom in sulfathiazole is ______.

46. According to Hückel criteria, sulfathiazole is predicted to be ___________.

48. This anion has______  electrons.

49. Consider the following two compounds.

18 2425. Review for test 1 (ch12-15). F17. Stafford

50. Consider the following compound.

Consider the following structure.

51. If named as an annulene, the name would be [ __ ] annulene.

52. This structure contains ____  electrons.

53. Using the Hückel criteria, the compound would be ______________.

Consider the following structure.

19 2425. Review for test 1 (ch12-15). F17. Stafford

20 2425. Review for test 1 (ch12-15). F17. Stafford

21 2425. Review for test 1 (ch12-15). F17. Stafford

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