Ch13 Test Bank Docx Ethers And Epoxides; Thiols And Sulfides

Organic Chemistry, 4e (Klein)

Chapter 13 Ethers and Epoxides; Thiols and Sulfides

1) Which of the compounds shown is(are) classified as ethers?

An illustration depicts the structures of four compounds.
Compound 1 has a SMILES string of C1CCOCC1.
Compound 2 has a SMILES string of COc1ccccc1.
Compound 3 has a SMILES string of CCOCC.
Compound 4 has a SMILES string of CCOC=C.

A) I

B) II and IV

C) III

D) I and III

E) all of these

Diff: 1

Learning Objective: 13.1 Describe the structure of ethers

2) What is the common name for CH3CH2CH2OCH2CH2CH3?

A) dibutyl ether

B) 1-propoxypropane

C) 1-propoxyhexane

D) dipropyl ether

E) none of these

Diff: 1

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

3) What is the common name for (CH3)2CHCH2OCH(CH3)2?

A) diisobutyl ether

B) isobutyl isopropyl ether

C) sec-butyl isopropyl ether

D) diisopropyl ether

E) none of these

Diff: 1

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

4) What is the IUPAC name for CH3CH2CH2CH2OCH2CH3?

A) 1-ethoxybutane

B) 1-butoxyethane

C) ethyl butyl ether

D) 1-ethoxyhexanea

E) none of these

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

5) What is the common name for the compound shown?

The bond-line structure of the compound has a SMILES string of CCC(C)OC(C)(C)C.

A) 1-butoxybutane

B) sec-butyl isopropyl ether

C) sec-butyl t-butyl ether

D) n-butyl isopropyl ether

E) none of these

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

6) What is the IUPAC name for CH3CH2OCH2CH2CH2CH2OCH2CH3?

A) 1,4-ethoxyoctane

B) diethoxy butyl ether

C) 1,2-diethoxymethane

D) 1,2-diethoxyhexane

E) 1,4-diethoxybutane

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

7) What is the correct structure for benzyl phenyl ether?

An illustration depicts the structures of four compounds.
Compound 1 has a SMILES string of c1ccc(cc1)Oc2ccccc2.
Compound 2 has a SMILES string of c1ccc(cc1)COCc2ccccc2.
Compound 3 has a SMILES string of Cc1ccc(cc1)Oc2ccc(cc2)C.
Compound 4 has a SMILES string of c1ccc(cc1)COc2ccccc2.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

8) What is the correct structure for dibenzyl ether?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

9) What is the IUPAC name for the compound shown?

The bond-line structure of the compound has an eight-carbon chain, in which C 2 is bonded to a methyl group and C 3 is bonded to an oxygen atom. The oxygen atom is further bonded to C 2 of a propyl side chain.

A) 2-methyl-3-oxy–4-isopropyloctane

B) 3-isopropoxy-2-methyloctane

C) 2-methyl-4-isopropoxyloctane

D) 2-methyl-3-oxy-4-tert-propyloctane

E) 6-isopropyl-6-isopropoxyoctane

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

10) What is the IUPAC name for the following compound?

The structure of the compound has a cyclohexane ring, in which C 1 is bonded to an ethoxy group and to a methoxy group, C 3 is bonded to a propyl side chain.

A) 1-methoxy-2-methoxy-3-propylcyclohexane

B) 3-ethoxy-3-methoxy-1-propylcyclohexane

C) 1-ethoxy-1-methoxy-3-propylcyclohexane

D) 3-ethoxy-3-methoxy-1-propylcyclohexone

E) 1-oxyethyl-1-oxymethyl-3-propylcyclohexane

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

11) What is the IUPAC name for the following compound?

The bond-line structure of the compound has a six-carbon chain, in which C 2 is double bonded to C 3, C 4 is bonded to an oxygen atom that is further bonded to C 2 of a propyl side chain, C 4 and C 5 are each bonded to a methyl group.

A) E-4-isopropoxy-4,5-dimethylhex-2-ene

B) Z-4-isopropoxy-4,5-dimethylhex-2-ene

C) E-1-methyl-2-oxo-3-isopropyl-3-methyl-5-heptene

D) Z-4-isopropoxy-4,5-methylhex-2-ene

E) E-4-isopropoxy-4,5-methylhex-2-ene

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

12) What is the IUPAC name for the following compound?

The structure of the compound has a cyclohexane ring, in which C 1 is wedge bonded to an oxygen atom that is further bonded to an ethyl group, and C 3 is dash bonded to a methyl group.

A) (1S,3R)-1-ethoxy-3-methylcyclohexane

B) (1R,3S)-1-ethoxy-3-methylcyclohexane

C) (1S,3S)-1-ethoxy-3-methylcyclohexane

D) (1R,3R)-1-ethoxy-3-methylcyclohexane

E) meso-ethoxy-3-methylcyclohexane

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

13) What is the IUPAC name for the following compound?

The structural formula of the compound has a central carbon single bonded to a methyl group and single bonded to three molecules of O C H 2 C H 3 groups.

A) 1-triethoxyethane

B) 2,2,3-triethoxyethane

C) 1,2,3-triethoxyethane

D) 1,1,1-triethoxyethane

E) 1,1,1-ethylether

Diff: 3

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

14) Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

15) Provide an IUPAC name for the following compound.

The structure of the compound has a benzene ring, in which C 1 is bonded to an oxygen atom that is further bonded to an ethyl group, C 2 is bonded to a methyl group, and C 4 is bonded to a tertiary-butyl group.

A) 4-butyl-1-ethoxy-2-methylbenzene

B) 1-t-butyl-4-ethoxy-3-methylbenzene

C) 1-butyl-4-ethoxy-3-methylbenzene

D) 4-t-butyl-1-ethoxy-2-methylbenzene

E) 4-t-butyl-1-ethoxy-2-methylcyclohexane

Diff: 3

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

16) Which choice shows the structure of (2S,5R)-5-ethoxy-2-octanol?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

17) Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

18) How many constitutional isomers with molecular formula C4H10O have an ether functional group?

A) none

B) one

C) three

D) six

E) nine

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

19) How many constitutional isomers with molecular formula C3H8O have an ether functional group?

A) 1

B) 5

C) 10

D) 15

E) 20

Diff: 2

Learning Objective: 13.2 Assign common and systematic (IUPAC) names to ethers

20) Which the compounds shown has the highest boiling point?

A) CH3CH2CH2CH2CH3

B) CH3CH2CH2CH2OH

C) CH3CH2CH2OCH3

D) CH3CH2CH2Cl

E) CH3CH2OCH2CH3

Diff: 1

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

21) Which of the compounds shown has the highest boiling point?

A) CH3CH2CH2CH2CH3

B) CH3CH2CH2CH2OH

C) CH3CH2CH2OCH3

D) CH3CH2CH2Cl

E) CH3CH2OCH2CH2OH

Diff: 1

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

22) Which the compounds shown is the least soluble in water?

A) diethyl ether

B) methyl propyl ether

C) 1-butanol

D) 2-butanol

E) pentane

Diff: 1

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

23) Rank the given compounds in decreasing order of boiling points (from highest to lowest boiling point).

An illustration depicts the condensed structural formulas of four compounds.
Compound 1: C H 3 C H 2 C H 2 C H 2 O H
Compound 2: C H 3 C H 2 O C H 2 C H 3
Compound 3: C H 3 O C H 3
Compound 4: H O C H 2 C H 2 C H 2 O H

A) II > IV > I > III

B) I > IV > II > III

C) IV > I > II > III

D) III > II > I > IV

E) IV > II > I > III

Diff: 2

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

24) Rank the compounds shown in decreasing order of solubility in water (from highest to lowest solubility).

An illustration depicts the condensed structural formulas of four compounds.
Compound 1: C H 3 C H 2 C H 2 C H 2 O H
Compound 2: C H 3 C H 2 O C H 2 C H 2 C H 3
Compound 3: C H 3 C H 2 O C H 2 C H 2 O H
Compound 4: C H 3 C H 2 O H

A) II > IV > I > III

B) I > IV > II > III

C) IV > I > II > III

D) III > II > I > IV

E) IV > III > I > II

Diff: 2

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

25) Which of the following compounds shown has highest boiling point?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

26) What molecular interactions in ethers are primarily responsible for their elevated boiling point relative to equivalent alkanes?

A) dipole-dipole interactions

B) ionic bonding

C) hydrophilic interactions

D) London dispersion forces

E) hydrogen bonding

Diff: 1

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

27) Ethers with larger alkyl groups have higher boiling points than equivalent ethers with smaller alkyl groups due to ________.

A) dipole-dipole interactions

B) ionic bonding

C) hydrophilic interactions

D) London dispersion forces

E) hydrogen bonding

Diff: 1

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

28) Identify a common ether solvent that was once used as an anesthetic.

A) diethyl ether

B) ethanol

C) methanol

D) isopropyl alcohol

E) dimethyl ether

Diff: 1

Learning Objective: 13.3 Discuss the effects of molecular weight on the boiling points of ethers

29) What is the IUPAC name for the following compound?

The structure of the compound has a SMILES string of C1COCCOCCOCCOCCO1.

A) 15-crown-5

B) 15-crown-4

C) 5-crown-15

D) 15-crown-15

E) none of these

Diff: 2

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

30) What is the correct IUPAC name for the following compound?

The structure of the compound has a SMILES string of C1COCCOCCOCCO1.

A) 12-crown-5

B) 12-crown-4

C) 4-crown-12

D) 12-crown-12

E) none of these

Diff: 2

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

31) Which of the following crown ether solvates lithium ions?

A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Diff: 1

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

32) Which of the following crown ether solvates potassium ions?

A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Diff: 1

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

33) Which of the following crown ether solvates sodium ions?

A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Diff: 1

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

34) Identify the missing reagent needed to carry out the reaction shown.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCCCBr reacts with N a F, benzene, and an unknown reagent depicted by a question mark to yield a product that has a SMILES string of CCCCF.

A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Diff: 2

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

35) Identify the missing reagent needed to carry out the reaction shown.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCCCBr reacts with L i F, benzene, and an unknown reagent depicted by a question mark to yield a product that has a SMILES string of CCCCF.

A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Diff: 2

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

36) Identify the missing reagent needed to carry out the reaction shown.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCCCBr reacts with K F, benzene, and an unknown reagent depicted by a question mark to yield a product that has a SMILES string of CCCCF.

A) 15-crown-5

B) 18-crown-6

C) 12-crown-4

D) 20-crown-3

Diff: 3

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

37) Identify the missing reagent needed to carry out the reaction shown.

An illustration shows a chemical reaction. The reactant that has a SMILES string of C1CCC=CC1 reacts with K M n O 4, benzene, and an unknown reagent depicted by a question mark to yield two products. The first product has a SMILES string of C1CC[C@@H]([C@@H](C1)O)O and the second product is enantiomer.

A) 18-crown-6

B) 12-crown-4

C) 20-crown-3

D) 15-crown-5

Diff: 3

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

38) All crown ethers are examples ________.

A) permanganates

B) cyclic polyethers

C) ionophones

D) linear polyethers

Diff: 1

Learning Objective: 13.4 Discuss the structures and utility of crown ethers

39) Predict the product for the reaction shown.

An illustration shows a partial reaction with no products mentioned. Two molecules of C H 3 C H 2 C H 2 O H react with H 2 S O 4 at 140 degrees Celsius.

A) propene

B) diethyl ether

C) 1-hexanol

D) 1-propoxypropane

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

40) Predict the product for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant 2-cyclopentylethanol reacts with H 2 S O 4 at 140 degrees Celsius.

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of C1CCC(C1)COCC2CCCC2.
Compound 2 has a five-carbon chain, in which C 3 is replaced by an oxygen atom. C 1 and C 5 are each bonded to C 1 of a cyclopentane ring.
Compound 3 has a SMILES string of C1CCC(C1)CC=O.
Compound 4 has a SMILES string of CCC1CCCO1.
Compound 5 has a SMILES string of C1CCC(C1)OC2CCCC2.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

41) Which illustration accurately shows the curved arrow mechanism for the initial step in the formation of the product shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of C(COCCO)O reacts with H 2 S O 4 to yield a product that has a SMILES string of C1COCCO1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

42) Can you prepare diisopropyl ether as the major product by heating 2-propanol in the presence of sulfuric acid?

A) Yes, because these conditions promote the substitution reactions.

B) Yes, because these conditions are highly favorable for

C) No, because secondary and tertiary alcohols undergo elimination reactions in these conditions.

D) No, because secondary and tertiary alcohols do not react in the presence of sulfuric acid.

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

43) Which one of the reactions shown would produce t-butyl methyl ether in high yield?

A) t-butyl chloride + sodium methoxide

B) t-butanol + methanol in presence of H2SO4 at 140°C

C) t-butyl bromide + bromomethane in the presence of NaOH

D) sodium t-butoxide + bromomethane

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

44) Which one of the reactions shown would produce t-butyl methyl ether in high yield?

A) CH3ONa + (CH3)3CBr

B) CH3OH + (CH3)3COH in the presence of H2SO4 at 140°C

C) CH3Cl + (CH3)3CBr in the presence of NaOH

D) (CH3)3CONa + CH3Br

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

45) Which one of the reactions shown would produce (S)-3-methoxyheptane in high yield?

A) sodium (S)-3-heptoxide + bromomethane

B) sodium (R)-3-heptoxide + bromomethane

C) sodium methoxide + (S)-3-bromoheptane

D) sodium methoxide + (R)-3-bromoheptane

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

46) Predict the product for the reaction shown.

An illustration a partial reaction with no products mentioned. The reactant that has a SMILES string of CCc1ccc(cc1)O reacts with N a H in the first step and C H 3 C H 2 C H 2 I in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

47) Provide the reagents necessary to carry out the following conversion.

An illustration shows a chemical reaction. The reactant that has a SMILES string of C1CCC(CC1)CCCO reacts to form a product that has a SMILES string of O(CCCc1ccccc1)C2CCCCC2.

A) 1. PBr3; 2. The structure of the compound has a benzene ring, in which C 1 is bonded to an O N a group.

B) 1. Hg(OAc)2, toluene; 2. NaBH4

C) 1. NaH; 2. bromobenzene

D) 1. MCBPA; 2. The structure of the compound has a SMILES string of COc1ccccc1.

E) 1. Excess HBr, heat; 2: toluene

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

48) Predict the product for the following reaction.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C(CCBr)CO reacts in the presence of N a H and heat.

An illustration depicts the structures of five compounds.
Compound 1 has a SMILES string of CCCCBr.
Compound 2 has a SMILES string of C(CC=O)CBr.
Compound 3 has a SMILES string of COC1CCC1.
Compound 4 has a SMILES string of C1CCC(C1)Br.
Compound 5 has a SMILES string of C1CCOC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

49) Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis.

The structure of the compound has a SMILES string of CCCOc1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

50) Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.5 Describe two methods for the preparation of ethers

51) Predict the product for the following reaction.

An illustration shows a partial reaction with no reactants mentioned. The reactant that has a five-carbon chain, in which C 1 is bonded to a hydroxyl group and a methyl group, C 5 is bonded to a bromine atom, reacts with sodium hydroxide, N a O H.

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of CC(C)CCCCBr.
Compound 2 has a SMILES string of CC1CCCCO1.
Compound 3 has a SMILES string of CC(C)CC(/C=C/Br)O.
Compound 4 has a cyclopentane ring, in which C 1 is bonded to an oxygen atom.
Compound 5 has a SMILES string of C1CCOCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

52) Identify the mechanism for the Williamson ether synthesis.

A) SN1 mechanism

B) SN2 mechanism

C) E1 mechanism

D) E2 mechanism

Diff: 1

Learning Objective: 13.5 Describe two methods for the preparation of ethers

53) Predict the product for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant, 3-methyl-2-pentene reacts with H g (O A c) 2, C H 3 C H 2 O H in the first step and N a B H 4 in the second step.

A) 3-methyl-3-pentanol

B) 3-ethoxy-3-methylpentane

C) 3-methyl-2-pentanol

D) 2-ethoxy-3-methylpentane

E) 1-ethoxy-3-methylpentane

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

54) Predict the product for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant, 1-ethylcyclohexene reacts with H g (O A c) 2, C H 3 C H 2 O H in the first step and N a B H 4 in the second step.

A) 1-ethylcyclohexanol

B) 2-ethoxy-1-ethylcyclohexane

C) 1-ethoxy-1-ethylcyclohexane

D) 2-ethoxy-3-ethylcyclohexane

E) 1-ethoxy-2-ethylcyclohexane

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

55) Predict the product for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCCCC(=C)C reacts with H g (O A c) 2, C H 3 O H in the first step and N a B H 4 in the second step.

A) 2-methyl-1-hexanol

B) 2-methoxy-2-methylhexane

C) 1-methoxy-2-methylhexane

D) 2-methoxy-3-methylhexane

E) 2-methyl-2-hexanol

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

56) Predict the product for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CC1=CCCC1 reacts with H g (O A c) 2, cyclopentanol that has a SMILES string of C1CCC(C1)O in the first step and N a B H 4 in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

57) Predict the product for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C/C=C/c1ccccc1 reacts with H g (O A c) 2, C H 3 C H 2 O H in the first step and N a B H 4 in the second step.

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of CC(c1ccccc1)OC.
Compound 2 has a SMILES string of CCC(c1ccccc1)O.
Compound 3 has a benzene ring, in which C 1 is bonded to a three-carbon chain. In the three-carbon chain, C 2 is bonded to an oxygen atom.
Compound 4 has a SMILES string of CCC(c1ccccc1)OCC.
Compound 5 has a SMILES string of CCC/C=C/c1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

58) What reagents are necessary to prepare the following compound using alkoxymercuration-demercuration?

The structure of the compound has a cyclohexane ring, in which C 1 is bonded to a methyl group and to an oxygen atom. The oxygen atom is bonded to a methylene group that is further bonded to C 1 of a cyclopentane ring.

A) I

B) II

C) III

D) I or II

E) II or III

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

59) Provide the reagents necessary to carry out the reaction shown.

An illustration shows a chemical reaction. The reactant that has a SMILES string of C=C1CCCCC1 is converted into the product that has a cyclohexane ring, in which C 1 is bonded to a methyl group and to an oxygen atom. The oxygen atom is further bonded to C 2 of a three-carbon chain.

A) 1. HBr; 2. H2, Pt; 3. NaOH

B) 1. excess HBr; 2.(CH3)2Br

C) 1. Hg(OAc)2, (CH3)2CHOH; 2. NaBH4

D) 1. Br2, H2O; 2. NaOH; 3. (CH3)CBr

E) 1. NaOH; 2. (CH3)CBr

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

60) Identify the conditions associated with oxymercuration-demercuration.

A) anti-Markovnikov, rearrangement possible

B) anti-Markovnikov, no rearrangement possible

C) Markovnikov, rearrangement possible

D) Markovnikov, no rearrangement possible

Diff: 3

Learning Objective: 13.5 Describe two methods for the preparation of ethers

61) Predict the product(s) for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCCOCC reacts with excess H B r and heat.

A) ethanol + 1-bromopropane

B) 1-propanol + bromoethane

C) 1-propanol + ethanol

D) 1-bromopropane + bromoethane

E) none of these

Diff: 2

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

62) Predict the product(s) for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCOc1ccccc1 reacts with excess H I and heat.

A) ethanol + phenol

B) phenol + iodoethane

C) iodobenzene + ethanol

D) iodobenzene + iodoethane

E) none of these

Diff: 2

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

63) Predict the product(s) for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of c1ccc(cc1)COc2ccccc2 reacts with excess H B r and heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

64) Predict the product(s) for the reaction shown.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C1CCOCC1 reacts with excess H I and heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

65) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C1CCOC1 reacts with excess H B r and heat.

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of C1CCC(C1)Br.
Compound 2 has a SMILES string of C1CC(C(C1)Br)Br.
Compound 3 has a SMILES string of C(CBr)CBr.
Compound 4 has a SMILES string of C(CCBr)CBr.
Compound 5 has a SMILES string of C(CCBr)CO.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

66) Predict the product(s) for the following reaction.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C1COCCO1 reacts with excess H I and heat.

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of C1CC(CCC1I)I.
Compound 2: Two molecules of a compound that has a SMILES string of C(CI)I.
Compound 3: Two molecules of a compound that has a SMILES string of C(CO)O.
Compound 4 has a SMILES string of C(CCBr)CCBr.
Compound 5 has a SMILES string of C(CCI)CCI.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

67) What is an accurate curved arrow mechanism for the formation of the product shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of c1ccc2c(c1)CCO2 reacts with excess H B r in the presence of heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

68) What is the expected product of the following reaction.

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CC1(CCCO1)C reacts with 1 mole of H I in the presence of heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

69) Predict the product(s) for the following reaction.

An illustration shows a partial reaction with no products mentioned and the structures of five compounds.
In a chemical reaction, the reactant that has a SMILES string of CC(C)OCCc1ccccc1 reacts with excess H B r in the presence of heat.

The structures of five compounds are as follows:
Compound 1 has a SMILES string of CC(C)Br.
Compound 2 has a three-carbon chain, in which C 2 is dash bonded to a methyl group and wedge bonded to a bromine atom.
Compound 3 has a SMILES string of c1ccc(cc1)Br.
Compound 4 has a SMILES string of c1ccc(cc1)CCBr.
Compound 5 has a SMILES string of CCCc1ccccc1.

A) I and II

B) II and III

C) III and IV

D) I and IV

E) II and V

Diff: 3

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

70) Explain why long-term storage of ethers can be problematic.

A) Ethers degrade in storage and become unreactive.

B) Ethers convert to esters during long periods of inertia.

C) When exposed to atmospheric oxygen, ethers form hydroperoxides that can explode on heating.

D) When isolated from atmospheric oxygen, ethers form highly explosive hydroperoxides.

Diff: 2

Learning Objective: 13.6 Describe the reaction of ethers with strong acids, and with oxygen

71) What is the IUPAC name for the compound shown?

The structure of the compound has a SMILES string of CCC1C(O1)C.

A) 3-ethyl-2-methyloxirane

B) 2-ethyl-3-methyloxirane

C) 2-ethyl-1-methyloxypentane

D) 1-ethyl-2-methyloxypentane

E) none of these

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

72) What is the IUPAC name for the compound shown?

The structure of the compound has a cyclopropane ring, in which C 1 is replaced by an oxygen atom, C 2 is bonded to an ethyl group and to a methyl group, C 3 is bonded to C 2 of a propyl side chain.

A) 2-ethyl-3-isopropyl-2-methyloxirane

B) 1-ethyl-2-isopropyl-1-methyloxirane

C) 2,4-dimethyloxyhexane

D) 1-ethyl-2,4-dimethyloxyhexane

E) 3-ethyl-2-isopropyl-3-methyloxirane

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

73) What is the structure of tetrahydrofuran?

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of C1CCCCC1.
Compound 2 has a SMILES string of C1CCCC1.
Compound 3 has a SMILES string of C1CCOC1.
Compound 4 has a SMILES string of C1CCOCC1.
Compound 5 has a SMILES string of O1CCOO1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

74) What is the structure for oxolane?

Five structures are shown:
A: The structure of the compound has a SMILES string of C1COC1.
B: The structure of the compound has a SMILES string of C1CCOCC1.
C: The structure of the compound has a SMILES string of C1CCOC1.
D: The structure of the compound has a cyclooctane ring, in which C 1 is replaced by an oxygen atom.
E: The structure of the compound has a SMILES string of C1CO1.

A) A

B) B

C) C

D) D

E) E

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

75) What is the structure for oxane?

A) A

B) B

C) C

D) D

E) E

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

76) What is the structure for oxetane?

A) A

B) B

C) C

D) D

E) E

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

77) What is the IUPAC name for the compound shown?

The structure of the compound has a cyclopropane ring, in which C 1 is replaced by an oxygen atom, C 2 is dash bonded to an ethyl group, and C 3 is wedge bonded to C 2 of a propyl side chain.

A) (2R, 3S)-2-ethyl-3-isopropyloxirane

B) (2S, 3S)-2-ethyl-3-isopropyloxirane

C) (2S, 3R)-3-ethyl-2-isopropyloxirane

D) (2S, 3S)-3-ethyl-2-isopropyloxirane

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

78) What is the IUPAC name for the compound shown?

The structure of the compound has a cyclopropane ring, in which C 1 is replaced by an oxygen atom, C 2 is dash bonded to an ethyl group, and C 3 is dash bonded to C 1 of a benzene ring.

A) (2S, 3R)-2-ethyl-3-phenyloxirane

B) (2R, 3S)-2-ethyl-3-phenyloxirane

C) (2S, 3S)-2-ethyl-3-phenyloxirane

D) (2S, 3R)-3-ethyl-2-phenyloxirane

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

79) What is the common name for the compound shown?

The structure of the compound has a SMILES string of C1COCCO1.

A) para-cyclodioxane

B) cyclodioxane

C) 1,4-dioxane

D) meta-cyclodioxane

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

80) What is the IUPAC name for the compound shown?

The structure of the compound has a cyclohexane ring, in which C 1 is wedge bonded to a methyl group. C 1 and C 2 are dash bonded to a common oxygen atom that forms an epoxide ring.

A) (1S,2R)-1-methyl-1,2-epoxycyclohexane

B) (1R,2R)-1-methyl-1,2-epoxycyclohexane

C) (1S,2R)-2-methyl-1,2-epoxycyclohexane

D) (1R,2S)-2-methyl-1,2-epoxycyclohexane

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

81) What is the structure of (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

82) What is the structure of (R)-2,2,3-trimethyl-3-phenyloxirane?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.7 Assign names to oxiranes (epoxides) by two methods

83) What is the expected product of the reaction shown?

(E)-2-pentene + mCPBA →

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

84) What is the expected product of the reaction shown?

(Z)-3-hexene + Mcpba →

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

85) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CC1=CCCC1 reacts with C H 3 (C double bond O) C O O H.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

86) What is the expected product of the reaction shown?

1-methylcyclohexene + mCPBA →

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

87) What reagent(s) are appropriate to carry out the reaction shown?

A) mCPBA

B) CH3CO3H

C) NaOH

D) A and B

E) B and C

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

88) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CC(C)CC=C reacts with B r 2 and H 2 O in the first step and N a O H in the second step.

An illustration depicts the structures of four compounds.
Compound 1 has a SMILES string of CC(C)CC(CO)Br.
Compound 2 has a SMILES string of CC(C)CC(=C)Br.
Compound 3 has a SMILES string of CC(C)CC(CBr)O.
Compound 4 has a SMILES string of CC(C)CC1CO1.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

89) What is the expected product of the following reaction?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCC(=C(C)C)C reacts with B r 2 and H 2 O in the first step and N a O H in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

90) What are the structures of compounds A and B in the reaction sequence shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC1=CCCCC1 reacts with B r 2 and H 2 O to form compound A. Compound A further reacts with N a O H to form compound B.

A) A is I and B is II

B) A is II and B is I

C) A is III and B is IV

D) A is IV and B is III

E) A is I and B is III

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

91) What is the expected product of the following reaction?

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

92) What reactants could be used to prepare the compound shown?

An illustration shows two products formed in a chemical reaction. The first product has a cyclopropane ring, in which C 1 is replaced by an oxygen atom, C 2 is dash bonded to C 1 of a cyclopentane ring, and C 3 is wedge bonded to a methyl group. The second product is an enantiomer.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

93) What reactants could be used to prepare the compound shown?

An illustration shows two products formed in a chemical reaction. The first product has a cyclohexane ring, in which C 1 is wedge bonded to an ethyl group, C 1 and C 2 are dash bonded to a common oxygen atom that forms an epoxide ring. The second product is an enantiomer.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

94) What reactants could be used to prepare the compound shown?

$An illustration shows five partial reactions with no products mentioned. Reaction 1: The reactant that has a SMILES string of CCCc1ccccc1 reacts with m C P B A. Reaction 2: The reactant that has a SMILES string of C=CCc1ccccc1 reacts with m C P B A. Reaction 3: The reactant that has a SMILES string of C=C\Cc1ccccc1\C=C reacts with m C P B A. Reaction 4: The reactant that has a SMILES string of Cc1ccccc1CC=C reacts with m C P B A. Reaction 5: The reactant that has a SMILES string of CC(C=C)c1ccccc1 reacts with m C P B A.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

95) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C1CC=C(C1)CO reacts with (C H 3) 3 C O O H, T i [O C H (C H 3) 2] 4, and (plus) D E T.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

96) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CC(C)/C(=C/CO)/C reacts with (C H 3) 3 C O O H, T i [O C H (C H 3) 2] 4, and (plus) D E T.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

97) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CC1(CCC(=CC1)CO)C reacts with (C H 3) 3 C O O H, T i [O C H (C H 3) 2] 4, and (negative) D E T.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

98) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of C/C=C/CO reacts with (C H 3) 3 C O O H, T i [O C H (C H 3) 2] 4, and (negative) D E T.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.8 Discuss two methods for the preparation of epoxides

99) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a cyclopentane ring, in which C 1 and C 2 are dash bonded to a common oxygen atom that forms an epoxide ring, reacts with hydronium ion, H 3 O superscript positive.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 1

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

100) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a cyclopropane ring, in which C 1 is replaced by an oxygen atom, C 1 is dash bonded to C 2 and C 3, C 2 is wedge bonded to a methyl group and single bonded to a methyl group, reacts with hydrogen bromide, H B r.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 1

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

101) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a cyclopropane ring, in which C 1 is replaced by an oxygen atom, C 2 is wedge bonded to an ethyl group and dash bonded to a methyl group, C 3 is wedge bonded to a methyl group, reacts with C H 3 O H and H 2 S O 4.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

102) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a cyclohexane ring, in which C 1 is fused with C 2 of an oxirane that has a SMILES string of C1CO1, reacts with C H 3 O H and H 2 S O 4.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

103) What is the likely product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a cyclohexane ring, in which C 1 and C 2 are dash bonded to a common oxygen atom that forms an epoxide ring and C 1 is wedge bonded to a methyl group, reacts with C H 3 C H 2 O H and H 2 S O 4.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

104) What reagents are suitable to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant that has a cyclopentane ring, in which C 1 is fused with C 2 of an oxirane that has a SMILES string of C1CO1 is converted into the product that has a cyclopentane ring, in which C 1 is bonded to a chlorine atom and to a methylene group that is further bonded to a hydroxyl group.

A) NaOH

B) H2SO4

C) HCl

D) H2O2

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

105) What reagents are necessary to carry out the conversion shown?

An illustration shows a partial reaction with no products mentioned. The reactant has a cyclohexane ring, in which C 1 is wedge bonded to a methyl group, C 1 and C 2 are dash bonded to a common oxygen atom that forms an epoxide ring, C 4 is dash bonded to C 2 of a three-carbon chain.

A) H2SO4

B) HCl

C) CH3OH/H2SO4

D) H3O+

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

106) What is the expected product of the reaction shown?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 1

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

107) Predict the product(s) of the reaction shown.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

108) What is the likely product of the reaction shown?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

109) What is the expected product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a cyclopentane ring, in which C 1 is fused to C 2 of an oxirane that has a SMILES string of C1CO1, reacts with C H 3 M g B r in the first step and H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

110) What is the expected product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

111) What reagents are appropriate to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC1=CCCCC1 reacts to form two products. The first product has a cyclohexane ring, in which C 1 is wedge bonded to a methyl group and dash bonded to a hydroxyl group, C 2 is wedge bonded to a methyl group. The second product is an enantiomer.

A) 1. mCPBA; 2. CH3MgBr; 3. H2O

B) 1. CH3MgBr; 2. H2O

C) 1. mCPBA; 2. H2O

D) mCPBA

Diff: 3

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

112) What reagents are appropriate to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant that has a cyclopentane ring, in which C 1 is wedge bonded to a methyl group, C 1 and C 2 are each dash bonded to a common oxygen atom that forms an epoxide ring, is converted into the product. The product has a cyclopentane ring, in which C 1 is wedge bonded to a methyl group and dash bonded to a hydroxyl group.

A) 1. LiAlH4; 2. H2O

B) 1. mCPBA; 2. CH3MgBr; 3. H2O

C) 1. H3O+; 2. NaOH

D) 1. LiAlH4; 2. NaOH

Diff: 3

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

113) What reagents are appropriate to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC1=CCCC1 reacts to form two products. The first product has a cyclopentane ring, in which C 1 is wedge bonded to a methyl group and dash bonded to a hydroxyl group, C 2 is wedge bonded to an N H 2 group. The second product is an enantiomer.

A) Excess HI, heat

B) MgBr, diethylether

C) 1. mCPBA; 2. NH3

D) 1. RCO3H; 2. H2O

Diff: 3

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

114) What reagents are appropriate to carry out the conversion shown?

A) 1. CH3MgBr; 2. H2O

B) 2. MCPBA; 2. H2O

C) 1. The structure of the compound has a SMILES string of c1ccc(cc1)C[Mg]Br. ; 2. H2O

D) 1. The structure of the compound has a SMILES string of CCc1ccccc1. ; 2. MgBrCH3; 3. H2O

E) 1. The structure of the compound has a SMILES string of Cc1ccccc1. ; 2. MgBr; 3. CH3CH3; 4. H2O

Diff: 3

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

115) What is an appropriate description of the curved arrow mechanism for the last step of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.10 Describe two types of ring-opening reactions of epoxides and discuss the stereochemical outcomes of these reactions

116) What is the correct structure for 3-methyl-1-hexanethiol?

An illustration shows the structures of five compounds.
Compound 1 has a seven-carbon chain, in which C 3 is bonded to an S H group.
Compound 2 has a cyclohexane ring, in which C 1 is replaced by an S H group and C 3 is bonded to a methyl group.
Compound 3 has a SMILES string of CCCC(C)CCS.
Compound 4 has a SMILES string of CC1CCCCC1S.
Compound 5 has a SMILES string of CCCC(S)CCC.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

117) What is the correct structure for phenylthiol?

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of C1=CC(C=C1)S.
Compound 2 has a cyclohexane ring, in which C 1 is replaced by an S H group.
Compound 3 has a benzene ring, in which C 1 is replaced by an S H group.
Compound 4 has a SMILES string of c1ccc(cc1)S.
Compound 5 has a SMILES string of c1ccc(cc1)Sc2ccccc2.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

118) What is the IUPAC name for the compound shown?

The bond-line structure of the compound has a seven-carbon chain, in which C 2 is bonded to an S H group and C 5 is bonded to a methyl group.

A) 2-sulfhydryl-5-methylheptane

B) 5-methyl-2-heptanethiol

C) 5-methyl-2-thiol-heptane

D) 2-sulfhydryl-5-ethylhexane

E) 2-mercapto-5-methylheptane

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

119) What is the IUPAC name for the compound shown?

The bond-line structure of the compound has a six-carbon chain, in which C 1 is bonded to a hydroxyl group, C 2 is bonded to a methyl group, and C 5 is bonded to an S H group.

A) 2--mercapto-5-methyl-6-hexanol

B) 1-hydroxy-2,5-methylhexanethiol

C) 5-mercapto-2-methyl-1-hexanol

D) 5-sulfhydryl-2-methyl-1-hexanol

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

120) What is the common name for the compound shown?

The bond-line structure of the compound has a five-carbon chain, in which C 1 is bonded to a sulfur atom that is further bonded to a methyl group.

A) pentyl methyl sulfide

B) methyl pentyl sulfhydryl

C) methyl pentyl sulfide

D) thio methyl pentyl

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

121) What is the IUPAC name for the compound shown?

The bond-line structure of the compound has a six-carbon chain, in which C 2 is bonded to a sulfur atom that is further bonded to an ethyl group.

A) 3-sulfide-4-methyl-octane

B) 2-ethylthiohexane

C) 2-methylthiohexane

D) 2-ethylsulfhydrylhexane

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

122) What is the expected product of the following reaction?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CC(C)CCCBr reacts with N a S H.

An illustration shows the bond-line structures of five compounds.
Compound 1 has a SMILES string of CCCCC(C)S.
Compound 2 has a SMILES string of CC(S)CCCBr.
Compound 3 has a SMILES string of CC(C)CCCS.
Compound 4 has a SMILES string of CCCC(C)CS.
Compound 5 has a SMILES string of CC(C)C(C)SC(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

123) What is the expected product for the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a central carbon single bonded to C H 2 C H 3 group, single bonded to O T s group, dash bonded to a hydrogen atom, and wedge bonded to a methyl group, reacts with N a S H.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

124) What is the expected product for the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a central carbon single bonded to C H 2 C H 3 group, single bonded to a chlorine atom, wedge bonded to a methyl group, and dash bonded to a hydrogen atom, reacts with C H 3 C H 2 S N a.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

125) What reagents are appropriate to carry out the following conversion?

An illustration shows a chemical reaction. The reactant that has a SMILES string of c1ccc(cc1)CBr reacts to form a product that has a SMILES string of c1ccc(cc1)CSc2ccccc2.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

126) What is the expected major product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCCSCC reacts with N a I O 4.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

127) What is the expected major product of the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCSC1CCCCC1 reacts with N a I O 4.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

128) What is the expected major product for the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCSC1CCCCC1 reacts with two molecules of H 2 O 2.

An illustration shows the structures of five compounds.
Compound 1 has a SMILES string of C1CCC(CC1)SCC(=O)O.
Compound 2 has a SMILES string of CS(=O)(=O)c1ccccc1.
Compound 3 has a SMILES string of C1CCC(CC1)S.
Compound 4 has a SMILES string of CCS(=O)(=O)C1CCCCC1.
Compound 5 has a SMILES string of CSC1CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

129) What is the expected major product for the reaction shown?

An illustration shows a partial reaction with no products mentioned. Two molecules of the reactant that has a SMILES string of C1CCC(CC1)S reacts with N a O H, H 2 O, and B r 2.

An illustration shows the structures of four compounds.
Compound 1 has a cyclohexane ring, in which C 1 is bonded to a sulfur atom that is further double bonded to an oxygen atom and single bonded to a bromine atom.
Compound 2 has a SMILES string of BrSC1CCCCC1.
Compound 3 has a SMILES string of C1CCC(CC1)S(=O)O.
Compound 4 has a SMILES string of C1CCC(CC1)SSC2CCCCC2.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

130) What is the expected major product for the reaction shown?

An illustration shows a partial reaction with no products mentioned. The reactant that has a SMILES string of CCSSCC reacts with Z n or H C l.

An illustration shows the bond-line structures of four compounds.
Compound 1 has a two-carbon chain, in which C 1 is bonded to a sulfur atom that is further bonded to another sulfur atom. The second sulfur atom is bonded to a chlorine atom.
Compound 2 has a SMILES string of CCSS.
Compound 3 has a SMILES string of CCSCl.
Compound 4 has a SMILES string of CCS.

A) I

B) II

C) III

D) IV

E) II and IV

Diff: 2

Learning Objective: 13.11 Discuss the reactions for the preparation and oxidation of thiols, including the oxidation products

131) What is an appropriate first step of a stepwise synthesis for the reaction shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of c1ccc(cc1)Br is converted into the product that has a SMILES string of CCC(=O)Cc1ccccc1.

A) Add Mg/ether

B) Add H2O

C) Add The structure of the compound has a SMILES string of CCC1CO1.

D) Add HCl

E) Add PCC

Diff: 2

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

132) What is an appropriate stepwise synthesis for reaction shown?.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC(=C)CCCCBr is converted into the product that has a cyclohexane ring, in which C 1 is replaced by an oxygen atom and C 2 is bonded to two methyl groups.

A) 1. NaOH; 2. H3O+

B) 1. HBr; 2. NaNH2

C) 1. H3O+; 2. NaOH

D) 1. HBr, peroxides; 2. NaOH; 3. H2, Pt

E) 1. PCC; 2. H3O+

Diff: 3

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

133) What is an appropriate stepwise synthesis for the reaction shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC1CCCCC1 reacts to form two products. The first product has a cyclohexane ring, in which C 1 is wedge bonded to a methyl group and dash bonded to a hydroxyl group, C 2 is wedge bonded to a three-carbon chain. The second product is an enantiomer.

A) 1. Br2, hv; 2. CH3CH2ONa; 3. CH3CH2CH2MgBr followed by H2O

B) 1. HBr; 2. CH3CH2ONa; 3. mCPBA; 4. CH3CH2CH2MgBr followed by H2O

C) 1. Br2, hv; 2. CH3ONa; 3. mCPBA; 4. CH3CH2CH2MgBr followed by H2O

D) 1. Br2, hv; 2. CH3CH2ONa; 3. mCPBA; 4. CH3CH2CH2MgBr followed by H2O

E) 1. HBr; 2. CH3CH2ONa; 3. mCPBA; 4. CH3CH2MgBr followed by H2O

Diff: 3

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

134) What is an appropriate stepwise synthesis for the reaction shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC(C)CCC=C is converted into the product that has a SMILES string of CC(C)CCC(CCC(C)C)O.

A) 1. mCPBA; 2. The structure of the compound has a SMILES string of CC(C)C[Mg]Br. followed by H2O

B) 1. mCPBA; 2. The structure of the compound has a SMILES string of CCC[Mg]Br. followed by H2O

C) 1. PCC; 2. The structure of the compound has a SMILES string of CCC[Mg]Br. followed by H2O

D) 1. HBr; 2. The structure of the compound has a SMILES string of CCC[Mg]Br. followed by H2O

E) 1. PCC; 2. The structure of the compound has a SMILES string of CC(C)C[Mg]Br. followed by H2O

Diff: 3

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

135) What is an appropriate stepwise synthesis for the reaction shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCC1=CCCCC1 is converted into the product that has a cyclohexane ring, in which C 1 is bonded to an ethyl group and C 2 is bonded to an oxygen atom that is further bonded to an ethyl group.

A) 1. HBr; 2. NaH; 3. CH3CH2I

B) 1. BH3-THF followed by H2O2/NaOH/H2O; 2. CH3CH2I

C) 1. BH3-THF followed by H2O2/NaOH/H2O; 2. NaH; 3. CH3CH2I

D) 1. BH3-THF followed by H2O2; 2.. NaH; 3. CH3I

E) 1. Br2 followed by H2O2/NaOH/H2O; 2. NaH; 3. CH3CH2I

Diff: 3

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

136) What is an appropriate stepwise synthesis for the reaction shown.

An illustration shows a chemical reaction. The reactant that has a SMILES string of C1CCC(=O)CC1 reacts to form two products. The first product has a cyclohexane ring, in which C 1 is dash bonded to a hydroxyl group and wedge bonded to a three-carbon chain, C 2 is wedge bonded to an oxygen atom that is further bonded to an ethyl group.

A) 1. H2SO4/heat; 2. mCPBA; 3. CH3CH2CH2ONa followed by H2O

B) 1. CH3CH2CH2MgBr followed by H2O; 2. H2SO4/heat; 3. CH3CH2CH2ONa followed by H2O

C) 1. PCC followed by H2O; 2. H2SO4/heat; 3. mCPBA; 4. CH3CH2CH2ONa followed by H2O

D) 1. CH3CH2CH2MgBr followed by H2O; 2. H2SO4/heat; 3. mCPBA; 4. CH3CH2CH2ONa followed by H2O

E) 1. CH3CH2MgBr followed by H2O; 2. H2SO4/heat; 3. mCPBA; 4. CH3CH2ONa followed by H2O

Diff: 3

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

137) What is an appropriate stepwise synthesis for the reaction shown?

An illustration shows a chemical reaction. The reactant that has a six-carbon chain, in which C 2 is bonded to a bromine atom and C 4 is bonded to a methyl group, is converted in to the product that has a SMILES string of CCC(C)CCCS.

A) 1. (CH3)3COK; 2. HBr/CH3OOCH3; 3. NaSH

B) 1. (CH3)3COK; 2. Br2/H2O; 3. NaSH

C) 1. (CH3)3COK; 2. HBr/H2O; 3. NaSH

D) 1. Hg(OAc)2, CH3OH; 2. NaBH4

E) 1. HBr, CH3OOCH3; 2. NaSH; 3. NaOH/H2O/Br2

Diff: 2

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

138) What is an appropriate stepwise synthesis for the reaction shown?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCC=C is converted into the product that has a SMILES string of CCCCSSCCCC.

A) 1. Br2, hv; 2. NaSH; 3. NaOH/H2O/Br2

B) 1. HBr, CH3OOCH3; 2. NaSH; 3. NaOH/H2O/Br2

C) 1. (CH3)3COK; 2. HBr/CH3OOCH3; 3. NaSH

D) 1. NaOH/H2O/Br2; 2. HBr/CH3OOCH3

E) 1. (CH3)3COK; 2. HBr; 3. NaSH

Diff: 2

Learning Objective: 13.12 Describe the synthetic utility of the ring-opening reaction of epoxides, including the reaction of epoxides with Grignard reagents

139) A compound with molecular formula C6H14O displays the following IR, 1HNMR and 13CNMR spectra. What is a consistent a structure for this compound?

IR: 1200cm-1

An illustration depicts the N M R spectrum of a compound. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right, ranging from 10 to 0, in decrements of 1. The spectrum has the following peaks: a triplet peak at 1 p p m labeled, 3 H, t; a singlet at 1.5 p p m labeled, 9 H, s; and a quintet at 3.5 p p m labeled, 2 H, q.

SDBS

An illustration depicts the N M R spectrum of a compound. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right, ranging from 70 to 0, in decrements of 10. The spectrum has the following peaks: a singlet at 15 p p m, a sharp singlet at 30 p p m, a singlet at 58 p p m, and a singlet at 70 p p m.

An illustration shows the bond-line structures of four compounds.
Compound 1 has a SMILES string of CC(C)(C)COC.
Compound 2 has a SMILES string of CCC(C)(C)OC.
Compound 3 has a SMILES string of CCOC(C)(C)C.
Compound 4 has a SMILES string of CCC(C)(C)OC.

A) I

B) II

C) III

D) IV

E) I or III

Diff: 2

Learning Objective: Spectroscopy

140) A compound with molecular formula C5H12O2 displays the following IR, 1H NMR and 13C NMR spectra. What is a consistent structure for this compound?

IR: 1200cm-1

An illustration shows the N M R spectrum of a compound. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right, ranging from 4 to 0, in decrements of 1. The spectrum has the following peaks: a singlet peak labeled, 6 is plotted at 1.4 p p m and a singlet peak labeled, 6 is plotted at 3.2 p p m.

An illustration shows the N M R spectrum of a compound. The horizontal axis plots parts per million, p p m and has a decreasing scale from left to right, ranging from 100 to 0, in decrements of 20. The spectrum has the following peaks: a singlet at 28 p p m, a singlet at 45 p p m, and a singlet at 100 p p m.

A) I

B) II

C) III

D) IV

E) I or II

Diff: 2

Learning Objective: Spectroscopy

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Chapter 13 Ethers And Epoxides; Thiols And Sulfides

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David R. Klein

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