Post on 11-Mar-2020
Chemistry 262
Winter 2018
Final Exam Practice
The following practice contains 44 problems and mimics Monday’s 150 point final,
which will also contain 44 problems valued at 3.5 points each – with approximately ½
of the problems drawn directly from the quarter’s homework. It will also contain 2
unknown analysis problems valued at 6 points/question. Apologies for the repeats
Name_____________________________________________________
CLASSIFICATION OF ALKYL HALIDES, ALCOHOLS, THIOLS, ETHERS, AND SULFIDES
1. Neopentyl alcohol is classified as a
a. 1o alcohol
b. 2o alcohol
c. 3o alcohol
d. 4o alcohol
e. None of the above
NOMENCLATURE OF ALKYL HALIDES, ALCOHOLS, THIOLS, ETHERS, AND SULFIDES
2. What is the correct IUPAC name for the following compound?
HO OH
a. 1,2-Butanediol
b. Isopropanol
c. 1-Propanol
d. 1,2-Propanediol
e. Propylene glycol
HOMOGENEOUS INTERMOLECULAR INTERACTIONS – BOILING POINTS AND MELTING POINTS
3. Which of the following would have the greatest boiling point?
a. Benzene
b. Cyclohexene
c. Hexanoic acid
d. Ethylene glycol
e. Sodium acetate
HOMOGENEOUS INTERMOLECULAR INTERACTIONS – HYDROGEN BONDING
4. Which of the following compounds has the lowest boiling point?
a. I
b. II
c. III
d. IV
e. V
HETEROGENEOUS INTERMOLECULAR INTERACTIONS – SOLUTIONS AND SOLUBILITY
5. In which of the following solvents would anhydrous MgSO4 be completely insoluble?
a. Water
b. Tetrahydrofuran
c. Dimethyl formamide
d. Dimethyl sulfoxide
e. Hexane
HETEROGENEOUS INTERMOLECULAR INTERACTIONS – SOLUTIONS AND SOLUBILITY
6. Which of the following compounds would have the greatest solubility in water?
a. Diethyl ether
b. Methyl propyl ether
c. 1-Butanol
d. 1,2-Butanediol
e. 4-Mercapto-1-butanol
I II III IV V
OOH
OH CH2OHOH
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – REACTION RATES
7. Consider the reaction of 2-iodopentane with acetate. Assuming no other changes to
the system, what effect on the rate would result from simultaneously doubling the
concentrations of both 2-iodopentane and acetate?
I
ONa
O OO
NaI
a. No effect
b. The rate would double (2x)
c. The rate would triple (3x)
d. The rate would increase 4 fold (4x)
e. The rate would increase 6 fold (6x)
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – TRANSITION STATE THEORY
8. Which of the following is true for any nucleophilic substitution reaction?
a. H > 0
b. H < 0
c. G‡ > 0
d. G > 0
e. G < 0
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – THE SN2 REACTION
9. When 0.10 mol of ICH2CH2CH2CH2Cl reacts with 0.10 mol of NaOCH3 at 40 oC, the
major product formed is
a. CH3OCH2CH2CH2CH2Cl
b. CH3OCH2CH2CH2CH2I
c. CH3OCH2CH2CH2CH2OCH3
d. CH2=CHCH2CH2Cl
e. CH2=CHCH2CH2I
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – STEREOCHEMISTRY
10. What would be the major product(s) of the following reaction?
CH2Cl
H CH3
OH
CH2OH
H3C H
CH2Cl
HO CH3
I
III
II
IV
CH2Cl
H OH
CH2OH
H CH3
SN2
a. I
b. II
c. III
d. IV
e. More than one of the above
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – CRITICAL FACTORS
11. Which of the following is the strongest nucleophile in an aprotic solvent such as
dimethylsulfoxide?
a. I
b. Br
c. Cl
d. F
e. All are equally nucleophilic in this environment
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – E2 REGIOCHEMISTRY
12. What is the principal product of the following reaction sequence?
a.
b.
c.
d.
e.
None of the above represents a significant product
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – E2 STEREOCHEMISTRY
13. What is major product of the following reaction?
a.
b.
c.
d.
e.
Br
1. t-BuOK, t-BuOH
2. H2, Pd/C, EtOH
Ot-Bu
Br
EtOH, EtONa
heat
OEt
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – FACTORS INFLUENCING SN1 AND E1 REACTIONS
14. Which statement(s) is/are true of acid-catalyzed alcohol dehydrations?
a. Protonation of the alcohol is a fast step
b. Formation of a carbocation from the protonated alcohol is a slow step
c. Rearrangements of less stable carbocations to more stable carbocations are
common
d. Loss of a proton by the carbocation is a fast step
e. All of the above
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – GENERAL PRODUCT PREDICTIONS
15. What are the principal products formed when 2-bromo-2-methylpentane reacts
with sodium propynide?
BrC: Na
I
HC CH
IV
II
V
HC CH
III
?
a. I
b. II
c. III
d. IV
e. V
NUCLEOPHILIC SUBSTITUTION AND -ELIMINATION REACTIONS – GENERAL PRODUCT PREDICTIONS
16. What would be the major product outcome for the following reaction?
HH3C
H Br
HH3C
H CN
CNH3C
H Br
I II
III IV
CNH3C
H H
HH3C
NC Br
C
25oC
a. I
b. II
c. III
d. IV
e. Equal amounts of I and III
ORGANOMETALLIC COMPOUNDS – FORMATION OF GRIGNARD AND ORGANOLITHIUM REAGENTS
17. Which of the following is the correct order of capacity towards Grignard formation,
from easiest to hardest?
RBr RCl RI RF
I II III IV
a. I, II, III, IV
b. III, I, II, IV
c. IV, II, I, III
d. III, I, IV, II
e. I, IV, III, II
ORGANOMETALLIC COMPOUNDS – REACTIONS OF GRIGNARD AND ORGANOLITHIUM REAGENTS
18. Which of the following reactions will not produce a primary alcohol?
a.
(CH3)2CHCH2CH2CHO
1. LiAlH4/Et2O
2. H3O+
b.
c.
d.
e.
CH2
O
CH2
(CH3)2CHCH2CH2MgBr
1.
2. H3O+
C6H5CCH3
O 1. NaBH4
2. H3O+
CH3CH2CH2CH2Li1. H2C=O
2. H3O+
CH3(CH2)5COOH1. LiAlH4, Et2O
2. H3O+
CARBENES, CARBENOIDS, AND THE SIMMONS-SMITH REACTION
19. What is the major product for the following reaction
a.
b.
c.
d.
e.
More than one of the above
ALCOHOL AND THIOL ACID BASE CONSIDERATIONS
20. Which of the following has the lowest pKa value in aqueous solution?
a. Mercaptoethane
b. Phenol
c. Phenyl mercaptan
d. tert-butyl alcohol
e. 1,2-ethanediol
DEHYDRATION OF ALCOHOLS
21. Carbocations are frequently intermediates in acidic reactions of alkenes, alcohols, etc.
Which of the following is a common carbocation property?
a. Rearrangement to a more stable carbocation
b. Loss of a proton to form an alkene
c. Combination with a nucleophile
d. Reaction with an alkene to form a larger carbocation
e. All of the above
I2CH2
Zn(Cu)
I I
I
REACTION OF ALCOHOLS WITH HYDROGEN HALIDES
22. Which of the following could be used to synthesize 2-chlorobutane?
a. CH3CH2CHCH2 + Cl2 (aq)
b. CH3CH2CHOHCH3 + HCl
c. CH3CH2CCH + HCl
d. CH3CH2CCH + Cl2
e. None of the above
BASE COMPATABLE ALCOHOL-DERIVED LEAVING GROUPS
23. What would be the principal product outcome of the following reaction sequence?
OH
H
CH3
H
pCH3C6H4SO2Cl
basetosylate
NaBr
ethanol
?
H
H
CH3
Br
Br
H
CH3
H
H
Br
CH3
Br
H
H
CH3
SO2C6H4CH3
I II III IV
a. I
b. II
c. III
d. IV
e. An equimolar ratio of II & III
MODERN METHODS FOR CONVERSION OF ALCOHOLS TO ALKYL HALIDES
24. Which reagent(s) would transform propyl alcohol into propyl bromide?
a. Conc. HBr/
b. PBr3
c. NaBr (aq)/
d. Two of the above
e. All of the above
ORGANIC REDOX REACTIONS
25. Which of the following is the correct order of decreasing level of oxidation?
HCOOH CH3OHCH2Cl2
I II III
a. I, II, III
a. III, II, I
b. II, III, I
c. II, I, III
d. I, III, II
OXIDATION OF ALCOHOLS
26. CrO3 in H2SO4/H2O will fail to give a positive test with which of these compounds?
a. CH3CH2CH2CH2OH
b.
c. (CH3)3COH
d.
e. All give a positive test with Jone’s reagent
OCTET EXPANSION AND OXIDATION OF THIOLS
27. Which of the following would oxidize a thiol to a sulfonic acid?
a. KMnO4
b. HNO3
c. HCl
d. Two of the above
e. All of the above
CH3CHCH2CH3
OH
CH3CH2CH2C O
H
SYNTHESIS OF ALCOHOLS
28. Which product(s) are the expected outcome of the following reaction sequence?
a. I
b. II
c. III
d. IV
e. V
INFRARED SPECTROSCOPY
29. An optically active compound of molecular formula C7H12, reacts with cold, dilute
KMnO4 and gives a characteristic IR band around 3300 cm-1. On catalytic
hydrogenation a new optically active compound is formed, with a formula C7H16. Which
of the following compounds is a possible candidate?
II III
IV V
I
a. I
b. II
c. III
d. IV
e. V
CH3
CH3
OH
CH3
OH
CH3H3C CH2OH
OOH
+
enantiomer
+
enantiomer
+
enantiomer
I II III IV V
1. BH3-THF
2. H2O2, NaOH?
1H-NMR SPECTROSCOPY – NUMBER OF RADIOFREQUENCY ABSORPTIONS
30. Assuming all are resolved, how many different signals would be observed in the 1H-NMR
of the following compound?
a. 1
b. 2
c. 3
d. 4
e. 5
1H-NMR SPECTROSCOPY – SPIN COUPLING AND CHEMICAL EQUIVALENCY
31. Predict the splitting pattern you would observe for the proton at C1 of 2,3-dimethyl-2-
phenylbutane
a. Singlet
b. Doublet
c. Quartet
d. Septet
e. Octet
1H-NMR SPECTROSCOPY – DESHIELDING AND SPIN COUPLING
32. Which of the following best represents the approximate predicted chemical shift and
coupling for the hydrogen indicated with the arrow?
a. 1.0 ppm, quartet
b. 2.4 ppm, singlet
c. 2.4 ppm, triplet
d. 2.4 ppm, quartet
e. 3.0 ppm, quartet
O
13C-NMR SPECTROSCOPY – CHEMICAL EQUIVALENCY, NUMBER OF SIGNALS, AND DESHIELDING
33. In 13C-NMR spectroscopy, which of the following functional groups gives rise to
the signal furthest downfield?
a. –CN
b.
c.
d.
e. –CC–
13
C-NMR SPECTROSCOPY – CHEMICAL EQUIVALENCY AND 13
C VS 1H ABSORPTIONS COMPARED
34. Assuming all peaks are resolved, which of the following would give rise to 4 peaks in
both the 1H-NMR and broadband decoupled 13C-NMR spectra?
a. I
b. II
c. III
d. IV
e. More than one of the above
MASS SPECTROMETRY – BASIC DEFINITIONS AND FRAGEMENTATION
35. Which of the following C6H14 compounds would give an MS base peak of m/z = 43?
a. CH3CH2CH2CH2CH2CH3
b. (CH3CH2)2CHCH3
c. (CH3)3CCH2CH3
d. (CH3)2CHCH(CH3)2
e. None of these
C O
C O
C X
I II III IV
Br
MASS SPECTROMETRY – BASIC DEFINITIONS AND FRAGEMENTATION
36. The data below for the isotope envelope of the molecular ion region of a halogen
containing species are consistent with the presence of what halogens for the compound
in question?
𝑀+⋅, I = 100.0 % 𝑀+⋅+ 2, I = 64.0 % 𝑀+⋅+ 4, I = 10.0 %
a. 1 Br
b. 1 Cl
c. 1 Br, 1 Cl
d. 2 Br
e. 2 Cl
SYNTHESIS OF ETHERS AND SULFIDES
37. What is the major product for the following reaction?
a.
b.
c.
d.
e. More than one of the above
Br2, CH3OH
+ enantiomerOH
Br
+ enantiomer
OCH3
Br
+ enantiomer
Br
H3CO
+ enantiomer
OCH3
Br
SYNTHESIS OF EPOXIDES
38. If cis-2-butene is treated with meta-chloroperbenzoic acid, what is the final product?
O
H3C CH3
H H
O
H3C H
H CH3
O
H3C H
H3C H
O
H3CH2C H
H H
I II III IV
a. I
b. II
c. III
d. IV
e. None of the above
EPOXIDES – NUCLEOPHILIC SUBSTITUTION REACTIONS
39. Which of the following is the principal product for the following reaction?
a. CH3CH2CH218OH
b.
c.
d.
e.
CH3CH
O
CH2 HA
H218O
?
CH3CHCH3
18OH
CH3CHCH2OH
18OH
CH3CH
OH
CH2
18OH
CH3CHCH218OH
18OH
EPOXIDES – NUCLEOPHILIC SUBSTITUTION REACTIONS
40. Which of the following is the principal product for the following reaction?
O
?CH3O-
CH3OH
OCH3OH
OCH3OCH3 OHOCH3 OHOH
I II III IV
H3O+
a. I
b. II
c. III
d. IV
e. Equal amounts of II & IV
ALKYNES – BASIC STRUCTURE AND NOMENCLATURE
41. What is the IUPAC name for the compound shown?
a. (S,E)-3-chlorohex-4-en-1-yne
b. (R,E)-3-chlorohex-2-en-5-yne
c. (S,E)-3-chlorohex-2-en-5-yne
d. (R,E)-3-chlorohex-4-en-1-yne
e. (R,E)-3-chloropent-4-en-1-yne
ALKYNES – ADDITION REACTIONS
42. Addition of excess HCl to 2-methyl-3-heptyne produces
a. 2-methyl-3,3-dichloroheptane
b. 2-methyl-2,3-dichloroheptane
c. 2-methyl-4,4-dichloroheptane
d. 2-methyl-3,4-dichloroheptane
e. 2-methyl-3-chloroheptene
f. More than one of the above
Cl
ALKYNES – ADDITION REACTIONS
43. What is the major product for the following reaction sequence?
a.
b.
c.
d.
e.
ALKYNES – REACTIONS OF TERMINAL ALKYNES
44. Which of the following would not be a successful method for preparing 5-
methyl-1-hexyne
a.
Br1) NaNH2 (2 mol), liq NH3
2) NH4+
b.
HC CNa Cl+ c.
LiHC CH+
d.
Br
Br
1) NaNH2 (3 mol), liq NH3
2) NH4+
e.
Br
Br1) NaNH2 (3 mol), liq NH3
2) NH4+
1. H2, Lindlars catalyst
2. Br2, CCl4
+ enantiomer
Br
Br
+ enantiomer
Br
Br
+ enantiomer
Br
+ enantiomerBr
Br Br
Br Br