CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
True/False
Indicate whether the statement is true or false.
____
1. An 1H NMR is run on a sample. This spectrum is shown below.
Based on this data the sample is probably an aldehyde.
____
2. Of the types of reactions that characterize carbonyl groups, the following reaction would be classified as
an α substitution.
____
3. The correct name for the following compound is 3-oxoheptanal.
____
4. The correct name for the following compound is trans-1,3-cyclopentanedicarbaldehyde.
____
5. Consider the following reaction.
The mechanism for this reaction is shown below.
pg. 1
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
____
6. Consider the following reaction.
The product of this reaction is a vicinal diol.
____
7. Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base. Bases
catalyze hydration by converting the water to hydroxide ion, a much better nucleophile
____
8. The product of the following reaction would be an imine.
____
9. The following compound would be classified as a hemiacetal..
____ 10. 3-hydroxybutanal can exist in equilibrium as a cyclic hemiacetal.
____ 11. The following compound can be produced by the reaction of cyclohexanecarbaldehyde and
.
____ 12. The structure of cis-1,3-cyclopentanedicarboxylic acid is shown below.
____ 13. Consider the data in the Table below to answer the following question:
Acidities of Substituted Benzoic and Acetic Acids
pKas at 25°C
pg. 2
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
Y−C6H4COOH
Y
H
CN
OCH3
Y−CH2COOH
4.75
2.47
3.57
meta
4.19
3.64
4.09
para
4.19
3.55
4.46
The structure of the strongest acid in the table above is NC−CH2−COOH.
____ 14. Consider the data in the Table below to answer the following question:
Y
H
CN
OCH3
Acidities of Substituted Benzoic and Acetic Acids
pKas at 25°C
Y−C6H4COOH
meta
Y−CH2COOH
4.75
4.19
2.47
3.64
3.57
4.09
para
4.19
3.55
4.46
The structure of the acid with the strongest conjugate base in the table above is CH3COOH.
____ 15. Benzoic acid can be produced by the treatment of bromobenzene with 1. Mg, ether, and 2.) CO2 followed
by acidification.
____ 16. Consider the following reaction.
The major organic product obtained is
____ 17. Consider the following reaction.
The major organic product obtained is
____ 18. Consider the following 1H NMR to answer the following question.
pg. 3
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and
Technology, 11-07-08)
This compound is known to contain both a −C=O group and an −OH group. Based on this spectrum, this
compound would be classified as aliphatic carboxylic acid.
____ 19. Based on the following IR spectrum, this compound would be classified as aromatic carboxylic acid.
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and
Technology, 11-07-08)
____ 20. Consider the following reaction.
The expected product is
pg. 4
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
____ 21. Malonic acid is an example of a β-ketoacid.
____ 22. The following compound should be named as cyanopropane.
____ 23. The product of the following reaction would be classified as a carboxylic acid.
____ 24. Both amides and nitriles are acyl derivatives of carboxylic acids.
____ 25. The correct name of the following structure is phenyl benzoate.
____ 26. Consider the following reaction.
The correct reactant to place in the box is PCl3.
____ 27. Consider the following reaction.
The reactant is a lactam.
____ 28. The correct name for the following compound is propyl cyclohexanoate.
pg. 5
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
____ 29. Consider the isotopically tagged substance below.
Saponification of this substance will produce the following products.
____ 30. Consider the following reaction.
The structure of the tetrahedral intermediate is
____ 31. Of the following substances,
the first and last substance shown are not derivatives of carboxylic acids.
____ 32. It is possible to directly convert an acid anhydride to an acid chloride.
Completion
Complete each statement.
Consider the reaction below to answer the following question(s). Use letters where appropriate to
answer the questions.
pg. 6
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
1. The nucleophile in this reaction is _____.
2. The catalyst in this reaction is _____.
3. The product of this reaction is called a(n)___________.
4. The first step in the reaction mechanism is the protonation of the ________group.
Consider each of the spectrum and answer the following questions using the appropriate number.
5. The peak labeled _____ would allow the distinction of an aldehyde from a ketone based on this spectrum.
6. The peak labeled _____ would allow the distinction of an aldehyde from a ketone based on this spectrum.
Answer each of the following questions with the appropriate number.
7. The number of α-hydrogens in the following compound is _____.
pg. 7
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
8. The number of hydrogens in the following compound that will be exchanged for deuterium upon reaction
with D2O and an acid catalyst is _____.
9. In the following compound, the most acidic hydrogen atom(s) are numbered as _____.
10. Of the compounds shown below, the one numbered _____ has the highest boiling point.
11. Of the compounds shown below, the one numbered _____ is an imine.
12. Of the compounds shown below, the one numbered _____ is an enamine.
13. Of the compounds shown below, the one numbered _____ is an enamine.
pg. 8
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
14. Provide the correct name for the following compound which can be used to produce aspirin.
15. When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is
acidified, ____________ _____ is produced.
16. The strongest acid of the following is indicated by the Roman numeral ______.
17. The strongest acid of the following is indicated by the Roman numeral ______.
Based on the informaton presented below, answer the following questions.
An ether solution contains the following components.
2,3,4,5-tetramethylbenzene
benzyl alcohol
2-hydroxybenzoic acid
This solution is extracted with a 1.0 M solution of NaOH, that is immiscible with ether.
18. The 2,3,4,5-tetramethylbenzene will be recovered from the _______ layer.
19. The benzyl alcohol will be recovered from the _______ layer.
20. The 2-hydroxybenzoic acid will be recovered from the _______ layer.
21. In order to recover the 2-hydroxybenzoic acid, a strong ______ must be added to the appropriate layer.
22. Ethyl propanoate (CH3CH2COOCH2CH3) can be prepared by the reaction of ethanol with ____________
acid.
23. Pentanoic acid can be converted to its methyl ester in very high yield by reaction with
___________________.
pg. 9
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
24. Consider the following spectrum of a carboxylic acid derivative.
This spectrum indicates the presence of a ___________group.
Consider the following general structures.
Use the Roman numeral of the substance to answer the following questions.
25. The substance that is the most reactive toward nucleophilic acyl substitution is _____.
26. The substance that is the least reactive toward nucleophilic acyl substitution is _____.
27. The substance that is classified as an anhydride is _____.
28. Consider the following 1H NMR spectrum.
The line indicated with the number _____ would indicate the presence of a C=O group.
29. Consider the structure given below.
The systematic name for this compound is:
30. Consider the following reaction.
pg. 10
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
The name of the product of this reaction is_______________________.
31. Consider the following reaction
The name of the reactant that should be placed in the box is _____________.
32. The structure that best describes the double bond character of the amide bond in acetamide is
shown by the Roman numeral _______.
Consider the following compounds.
Use the numbers shown to answer the following questions.
the word none.
33. A lactone is represented by the structure numbered ____.
34. An anhydride is represented by the structure numbered ____.
35. An imide is represented by the structure numbered ____.
Problem
1. What is the IUPAC name of the following compound?
pg. 11
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
If none of the structures is applicable enter
2. What is the IUPAC name of the following compound?
3. What is the major organic product obtained from the following reaction?
4. What is the major organic product obtained from the following reaction?
5. What is the major organic product obtained from the following reaction?
6. What is the major organic product obtained from the following reaction?
7. What is the major organic product obtained from the following reaction?
pg. 12
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
8. What is the major organic product obtained from the following reaction?
9. What is the major organic product obtained from the following reaction?
10. What is the major organic product obtained from the following reaction?
11. What is the major organic product obtained from the following reaction?
12. What is the major organic product obtained from the following reaction?
13. What is the major organic product obtained from the following reaction?
14. What is the major organic product obtained from the following reaction?
pg. 13
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
15. What is the major organic product obtained from the following reaction?
16. What is the major organic product obtained from the following sequence of reactions?
17. What is the major organic product obtained from the following sequence of reactions?
18. What is the major organic product obtained from the following sequence of reactions?
19. What is the major organic product obtained from the following sequence of reactions?
20. What is the IUPAC name of the following compound?
21. What is the IUPAC name of the following compound?
pg. 14
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
22. What is the major organic product obtained from the following reaction?
23. What is the major organic product obtained from the following reaction?
24. What is the major organic product obtained from the following reaction?
25. What is the major organic product obtained from the following reaction?
26. What is the major organic product obtained from the following reaction?
pg. 15
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
27. What is the major organic product obtained from the following reaction?
28. What is the major organic product obtained from the following reaction?
29. What is the major organic product obtained from the following reaction?
30. What is the major organic product obtained from the following sequence of reactions?
31. What is the major organic product obtained from the following sequence of reactions?
32. What is the IUPAC name of the following compound?
33. What is the IUPAC name of the following compound?
pg. 16
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
34. What is the major organic product obtained from the following reaction?
35. What is the major organic product obtained from the following reaction?
36. What is the major organic product obtained from the following reaction?
37. What is the major organic product obtained from the following reaction?
38. What two organic compounds are obtained from the following reaction?
39. What two organic compounds are obtained from the following reaction?
pg. 17
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
40. What two organic compounds are obtained from the following reaction?
41. What two organic compounds are obtained from the following reaction?
42. What is the major organic product obtained from the following reaction?
43. What is the major organic product obtained from the following reaction?
44. What is the major organic product obtained from the following reaction?
45. What is the major organic product obtained from the following reaction?
pg. 18
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
46. What is the major organic product obtained from the following reaction?
47. What is the major organic product obtained from the following reaction?
48. What is the major organic product obtained from the following reaction?
49. What is the major organic product obtained from the following reaction?
50. What is the major organic product obtained from the following sequence of reactions?
51. What is the major organic product obtained from the following sequence of reactions?
pg. 19
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
pg. 20
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
Answer Section
TRUE/FALSE
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
T
T
F
F
T
F
T
F
T
F
F
T
T
T
T
F
F
F
T
T
F
F
T
F
T
F
F
F
F
F
T
F
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
COMPLETION
1. ANS: A
PTS: 1
2. ANS: C
PTS: 1
pg. 21
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
3. ANS: acetal
PTS: 1
4. ANS:
carbonyl
ketone
PTS: 1
5. ANS: 2
PTS: 1
6. ANS: 1
PTS: 1
7. ANS:
4
four
PTS: 1
8. ANS:
4
four
PTS: 1
9. ANS:
2
two
PTS: 1
10. ANS:
2
two
PTS: 1
11. ANS:
2
two
PTS: 1
12. ANS:
3
three
PTS: 1
13. ANS:
3
three
PTS: 1
14. ANS:
pg. 22
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
o-hydroxybenzoic acid
o-hydroxybenzoic acid
2-hydroxybenzoic acid
PTS: 1
15. ANS:
phenylacetic acid
phenylethanoic acid
PTS: 1
16. ANS: IV
PTS: 1
17. ANS: III
PTS: 1
18. ANS: ether
PTS: 1
19. ANS: ether
PTS: 1
20. ANS:
base
basic
NaOH
aqueous
PTS: 1
21. ANS: acid
PTS: 1
22. ANS:
propanoic
propionic
PTS: 1
23. ANS: diazomethane
PTS: 1
24. ANS: nitrile
PTS: 1
25. ANS: IV
PTS: 1
26. ANS: II
PTS: 1
27. ANS: 1
pg. 23
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
28. ANS: 5
PTS: 1
29. ANS:
Ethyl p-aminobenzoate
ethyl p-aminobenzoate
Ethyl 4-aminobenzoate
ethyl 4-aminobenzoate
PTS: 1
30. ANS: hexane-2,6-diol
PTS: 1
31. ANS:
methanol
methyl alcohol
PTS: 1
32. ANS: II
PTS: 1
33. ANS:
1
one
PTS: 1
34. ANS:
2
two
PTS: 1
35. ANS:
3
three
PTS: 1
PROBLEM
1. ANS:
(S)-2-chloropentanal
PTS: 1
2. ANS:
(S)-3-methyl-2-pentanone
PTS: 1
pg. 24
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
3. ANS:
PTS: 1
4. ANS:
PTS: 1
5. ANS:
PTS: 1
6. ANS:
PTS: 1
7. ANS:
PTS: 1
8. ANS:
PTS: 1
9. ANS:
PTS: 1
10. ANS:
pg. 25
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
11. ANS:
PTS: 1
12. ANS:
PTS: 1
13. ANS:
PTS: 1
14. ANS:
PTS: 1
15. ANS:
PTS: 1
16. ANS:
pg. 26
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
17. ANS:
PTS: 1
18. ANS:
PTS: 1
19. ANS:
PTS: 1
20. ANS:
(Z)-2-butenoic acid
PTS: 1
21. ANS:
(E)-3-pentenoic acid
PTS: 1
22. ANS:
PTS: 1
23. ANS:
PTS: 1
24. ANS:
pg. 27
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
25. ANS:
PTS: 1
26. ANS:
PTS: 1
27. ANS:
PTS: 1
28. ANS:
PTS: 1
29. ANS:
pg. 28
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
30. ANS:
PTS: 1
31. ANS:
PTS: 1
32. ANS:
(Z)-ethyl 2-methyl-2-butenoate
PTS: 1
33. ANS:
(Z)-N,N-dimethyl-3-pentenamide
PTS: 1
34. ANS:
PTS: 1
35. ANS:
PTS: 1
36. ANS:
PTS: 1
37. ANS:
pg. 29
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
38. ANS:
PTS: 1
39. ANS:
PTS: 1
40. ANS:
PTS: 1
41. ANS:
PTS: 1
42. ANS:
PTS: 1
43. ANS:
pg. 30
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
44. ANS:
PTS: 1
45. ANS:
PTS: 1
46. ANS:
PTS: 1
47. ANS:
PTS: 1
48. ANS:
PTS: 1
49. ANS:
pg. 31
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)
PTS: 1
50. ANS:
PTS: 1
51. ANS:
PTS: 1
pg. 32
CHEM 2425. Review for Test 3 (chapter 19, 20, 21)