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

1 2425. 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. 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. M1cm

1

b. Mcm

c. Jmol1M

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 cm1

b. 2500 to 2000 cm1

c. 2000 to 1500 cm1

d. below 1500 cm1

1. _____ CC, CO, CN, and CX single-bond vibrations.

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

3. _____ NH, CH, and OH 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 cm1

b. 2500 to 2000 cm1

c. 2000 to 1500 cm1

d. below 1500 cm1

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 13

C 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 60C 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.


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.



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.



1H NMR spectrum.


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 CC 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

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

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