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