10/18/23, 2:38 PM CHEM201-FinalExam-Answers

1 Benzyne is a very reactive intermediate. As a result, it is very difficult to track chemical reactions. How was its existence demonstrated?

Choose one answer. a. By trapping the intermediate in a cycloaddition reaction

b. By separating it from the mixture by GC/MS

c. By separating it from the mixture by column chromatography

d. None of the above

2 Benzyne is the mechanistic intermediate for which of the following reactions?

Choose one answer. a. Nucleophilic additions

b. Electrophilic additions

c. Cycloadditions

d. All of the above

3 Chain reactions involving free-radicals occur in which of the following orders?

Choose one answer. a. Initiation, propagation, termination

b. Initiation, termination, propagation

c. Propagation, termination, initiation

d. Termination, propagation, initiation

4 Given that the energy of a CH3-H bond is 104 kcal/mol and that of an HO-H bond is 119 kcal/mol, what is the bond dissociation energy of the
following reaction?

Choose one answer. a. 15 kcal/mol

b. -15 kcal/mol

c. 223 kcal/mol

d. -223 kcal/mol

5 Given that the energy of a CH3bond is 104 kcal/mol, CH3-Cl bond is 85 kcal/mol, H-Cl bond is 103 kcal/mol and that of an Cl2 bond is 58 kcal/mol,
what is the bond dissociation energy of the following reaction?

Choose one answer. a. 25 kcal/mol

b. -25 kcal/mol

c. 189 kcal/mol

d. -166 kcal/mol

6 Identify the most stable free radical.

Choose one answer. a. I

b. II

c. III

d. IV

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7 Nitrogen ylides are very versatile and can be used in a number of chemical reactions. Which of the following is a reaction of nitrogen ylides?

Choose one answer. a. Cannizzaro reaction

b. Sommelet reaction

c. Blanc reaction

d. Friedel-Crafts reaction

8 Nitrogen ylides are very versatile and can be used in a number of chemical reactions. Which of the following reactions is NOT a reaction of nitrogen
ylides?

Choose one answer. a. Stevens reaction

b. Sommelet reaction

c. Wittig reaction

d. Friedel-Crafts reaction

9 The Wittig reagent was allowed to react with and carbonyl compound with the formula C10H12O. The name of the product was 4-phenyl-4-octene.
What is the name of the carbonyl compound used?

Choose one answer. a. 1-phenyl-1-butanone

b. Acetophenone

c. 2-phenyl-3-butanone

d. Benzaldehyde

10 What are common methods for preparing benzyne?

Choose one answer. a. Elimination from organolithium or organomagnesium precursors

b. loss of neutral leaving group

c. photolytic and/or pyrolitic methods

d. All of the above

11 What is the major product of the radical reaction of 2-methylbutane with Cl2?

Choose one answer. a. 2-chloro-2-methylbutane

b. 1-chloro-2-methylbutane

c. 3-chloro-2-methylbutane

d. 4-chloro-2-methylbutane

12 Which halogen is most reactive in radical halogenations of alkanes?

Choose one answer. a. F2

b. Cl2

c. Br2

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d. I2

13 Which of the following is NOT a method for generating free radicals?

Choose one answer. a. Thermal cracking

b. Photolysis bond heterolysis

c. Homolysis of peroxides and azo compounds

d. Electron transfer

14 Which of the following is NOT a precursor of Benzyne?

Choose one answer. a. I

b. II

c. III

d. IV

15 Which of the following molecules is a nitrogen ylide?

Choose one answer. a. I

b. II

c. III

d. IV

16 Which of the following molecules is a phosphorus ylide?

Choose one answer. a. I

b. II

c. III

d. IV

17 Which of the following molecules is a sulfur ylide?

Choose one answer. a. I

b. II

c. III

d. IV

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18 Which of the following six-carbon molecules will form a single chlorinated compound when reacting with chlorine in presence of light.

Choose one answer. a. I

b. II

c. III

d. All of them

19 Which of the following Wittig reagents would be useful for converting acetophenone into 1,1-diphenylethene?

Choose one answer. a. I

b. II

c. III

d. IV

20 Which statement about free radicals is incorrect?

Choose one answer. a. Free radicals contain an unpaired electron.

b. Radicals are believed to be involved in degenerative diseases and cancers.

c. They are formed by heterolytic cleavage of bonds.

d. Radicals can either be neutral or ionic.

21 1-chloro-3-methylhexane undergoes SN2 reaction with sodium ethoxide. This reaction yields low amount of products. However, addition of small
amounts of sodium iodide increases the rate of the reaction. Why?

Choose one answer. a. The charge of the sodium ion stabilizes the charge of the chloride ion.

b. The iodide ion renders the ethoxide ion more reactive.

c. Small amounts of alkyl chlorides are converted into the more reactive alkyl iodides.

d. With the presence of NaI, the mechanism changes to Sn1.

22 Compound A undergoes a rearrangement reaction and forms compounds B and C. Based on the potential energy diagram below, what can be said
about compounds B and C in terms of kinetics and thermodynamics?

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Choose one answer. a. B is the kinetic and thermodynamic product.

b. B is the kinetic product, and C is the thermodynamic product.

c. C is the kinetic product, and B is the thermodynamic product.

d. C is the kinetic and thermodynamic product.

23 Provide the IUPAC name, including stereochemical designation, for the following molecule.

Choose one answer. a. (2R,3R)-2,3-dibromopentane

b. (2S,3S)-2,3-dibromopentane

c. (2R,3S)-2,3-dibromopentane

d. (2S,3R)-2,3-dibromopentane

24 Select the mechanism by which the reactants below will react.

Choose one answer. a. SN1

b. SN2

c. E1

d. E2

25 Vinyl chloride, shown below, does not react with sodium hydroxide in SN2 reactions. Why?

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Choose one answer. a. Hydroxide is a weak nucleophile.

b. The sp2 carbon-chlorine bond is stronger than the sp3 carbon-chlorine bond.

c. The chlorine atom is sterically crowded.

d. Both B and C

26 What is the configuration at the carbons labeled 1 and 2 in the following compound?

Choose one answer. a. 1R, 2S

b. 1S, 2R

c. 1R, 2R

d. 1S, 2S

27 What is the major product of the following reaction?

Choose one answer. a. I

b. II

c. III

d. IV

28 What is the relationship between the two compounds below?

Choose one answer. a. Same compound

b. Structural isomers

c. Enantiomers

d. Diastereomers

29 What reaction will the following compound most likely undergo?

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Choose one answer. a. SN1

b. SN2

c. E1

d. E2

30 Which is the correct structural formula for the compound formed according to the mechanism below (lone electron pairs were omitted)?

Choose one answer. a. I

b. II

c. III

d. IV

31 Which of the following alkyl halides give only one alkene as the product in the E2 reaction?

Choose one answer. a. I

b. II

c. III

d. IV

32 Which of the following carbocations is most stable?

Choose one answer. a. I

b. II

c. III

d. IV

33 Which of the following compound h as the IUPAC name of (2R, 3R)-2, 3-dihydroxybutane?

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Choose one answer. a. I

b. II

c. III

d. IV

34 Which of the following compounds is chiral?

Choose one answer. a. I

b. II

c. III

d. IV

35 Which of the following compounds will be the most reactive substrate in SN1 reactions?

Choose one answer. a. (C2H5)3CCl

b. (C2H5)2CHCl

c. C2H5CH2Cl

d. (C2H5)3CF

36 Which of the following compounds will most readily react in S¬N1 reactions?

Choose one answer. a. I

b. II

c. III

d. IV

37 Which of the following molecules is prochiral?

Choose one answer. a. I

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b. II

c. III

d. IV

38 Which of the following statements about chirality is incorrect?

Choose one answer. a. A chiral center is an atom that is tetrahedrally bonded to four different groups.

b. A chiral molecule has a superimposable mirror image.

c. A chiral molecule does not have any reflective symmetry.

d. All chiral molecules may exist as enantiomers.

39 Which of the following statements about the chemical reaction described below is true?

Choose one answer. a. The product will have R configuration.

b. The product will have S configuration.

c. The product will be achiral.

d. The product will be a racemic mixture.

40 Which of the following statements best describes an E2 reaction?

Choose one answer. a. It involves a two-step mechanism.

b. It involves a very reactive intermediate.

c. The rate of the reaction depends on the concentration of the base.

d. The rate of the reaction increases in polar solvents.

41 Name the following compound.

Choose one answer. a. Phenylmagnesium bromide

b. Ethylphenylmagnesium bromide

c. Benzylmagnesium bromide

d. Benzylicmagnesium bromide

42 The Grignard reaction is an important reaction to provide which of the following?

Choose one answer. a. Carbon-carbon bonds

b. Carbon-magnesium bonds

c. Carbon-halide bonds

d. Magnesium-halide bonds

43 What happens to the chiral center when (R)-3-methyl-3-phenyl-4-heptanone reacts with phenylmagnesium bromide?

Choose one answer.

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a. Inversion of configuration occurs.

b. A racemic mixture is formed.

c. Nothing, the chiral center remains unchanged.

d. The product is achiral.

44 What is organometallic chemistry?

Choose one answer. a. The study of carbon containing compounds

b. The study of compounds containing a carbon-metal bond

c. The study of metals

d. The study of salts

45 What is the chemical structure of furan?

Choose one answer. a. I

b. II

c. III

d. IV

46 What is the IUPAC name for the imidazole molecule, shown below?

Choose one answer. a. Imidazole

b. 1,3-imidazole

c. Diazole

d. 1,3-diazole

47 What is the major product of the following reaction?

Choose one answer. a. I

b. II

c. III

d. IV

48 What is the major product of the following reaction?

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Choose one answer. a. I

b. II

c. III

d. IV

49 What is the name of the following heterocycle?

Choose one answer. a. Isoquinoline

b. Indole

c. Quinoline

d. Pyrrolidine

50 What is the name of the following heterocycle?

Choose one answer. a. Isoquinoline

b. Indole

c. Quinoline

d. Pyrrolidine

51 What is the name of the following heterocycle?

Choose one answer. a. Thiazole

b. Indole

c. Quinoline

d. Pyrrolidine

52 Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?

Choose one answer. a. CH3CH2CH(OH)CH2Br

b. BrCH2CO2H

c. PhCH2CH2Br

d. None of these are suitable

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53 Which of the following heterocycles is most basic?

Choose one answer. a. I

b. II

c. III

d. IV

54 Which of the following is an organometallic compound?

Choose one answer. a. I

b. II

c. III

d. IV

55 Which of the following molecules is an heterocycle?

Choose one answer. a. I

b. II

c. III

d. IV

56 Which of the following molecules will NOT be a product of the following reaction?

Choose one answer. a. I

b. II

c. III

d. All of the above

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57 Which of the following reactions would be a useful way of preparing 1-phenyl-1-butanol?

Choose one answer. a. Butanal and phenylmagnesium bromide

b. 1-phenyl-3-butanone and NaBH4

c. Propanal and benzylmagnesium bromide

d. Both A and C

58 Which of the heterocyclic compounds shown below is most acidic?

Choose one answer. a. I

b. II

c. III

d. IV

59 Which of the heterocyclic compounds shown below is most basic?

Choose one answer. a. I

b. II

c. III

d. IV

60 Which reagent is best for the reaction below?

Choose one answer. a. I

b. II

c. III

d. None of the above

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