Organic Chemistry 11th Edition by Francis Carey - Test Bank

Organic Chemistry 11th Edition by Francis Carey – Test Bank

 

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Organic Chemistry, 11e (Carey)

Chapter 5   Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms Nucleophilic Substitution

 

1) The structure below is a generalized abbreviation for which class of compounds?

1. A) ketones
2. B) aldehydes
3. C) carboxylic acids
4. D) esters

 

Answer:  B

Difficulty: 1 Easy

Section:  05.01

Topic:  Functional Groups

Bloom’s:  1. Remember

Chapter:  05

Subtopic:  C=O containing functional groups

 

2) Identify the functional group in the boxed area.

1. A) ester
2. B) ketone
3. C) carboxylic acid
4. D) ether

 

Answer:  A

Difficulty: 2 Medium

Section:  05.01

Topic:  Functional Groups

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  C=O containing functional groups

 

 

 

3) What is the IUPAC name of the compound below?

1. A) 8-chloro-4-isopropyl-4,7-dimethylnonane
2. B) 2-chloro-6-isopropyl-3,6-dimethylnonane
3. C) 2-chloro-3,6,7-trimethyl-6-propyloctane
4. D) 6-sec-butyl-2-chloro-3,6-dimethyloctane

 

Answer:  B

Difficulty: 2 Medium

Section:  05.02

Topic:  Alkyl Halides

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC nomenclature of alkyl halides

 

4) What is the IUPAC name of the compound below?

1. A) 5,5-dimethyl-2-hexanol
2. B) 2,2-dimethyl-5-hexanol
3. C) 5,5-dimethyl-2-pentanol
4. D) 2,2-dimethyl-5-pentanol

 

Answer:  A

Difficulty: 2 Medium

Section:  05.03

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

 

 

5) What is the IUPAC name of the compound below?

1. A) 3-isobutyl-2-hexanol
2. B) 2-methyl-5-(1-hydroxyethyl)octane
3. C) 2-methyl-5-propyl-6-heptanol
4. D) 6-methyl-3-propyl-2-heptanol

 

Answer:  D

Difficulty: 2 Medium

Section:  05.03

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

6) What is the IUPAC name of the following compound?

 

1. A) cis-3-methylcyclohexanol
2. B) trans-3-methylcyclohexanol
3. C) cis-5-methylcyclohexanol
4. D) trans-5-methylcyclohexanol

 

Answer:  B

Difficulty: 2 Medium

Section:  05.03

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

 

 

7) What is the IUPAC name of the following compound?

1. A) 3-methyl-2-butanol
2. B) 3-methyl-3-butanol
3. C) 2-methyl-2-butanol
4. D) 2,2-dimethyl-1-butanol

 

Answer:  C

Difficulty: 2 Medium

Section:  05.03

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

 

 

8) What is the name of the following compound?

1. A) cis-3-methylcyclohexanol
2. B) cis-2-methylcyclopentanol
3. C) trans-3-methylcyclohexanol
4. D) trans-3-methylcyclopentanol

 

Answer:  C

Difficulty: 3 Hard

Section:  05.03

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

9) What is the IUPAC name of the following alcohol?

1. A) trans-4-methylcyclohexanol
2. B) trans-3-methylcyclohexanol
3. C) cis-4-methylcyclohexanol
4. D) cis-3-methylcyclohexanol

 

Answer:  A

Difficulty: 3 Hard

Section:  05.03

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

10) Which of the following is isobutyl alcohol?

1. A) CH3CH2CH2CH2OH
2. B) CH3CH2CH(OH)CH3
3. C) (CH3)2CHCH2OH
4. D) (CH3)3COH

 

Answer:  C

Difficulty: 2 Medium

Section:  05.03

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

11) Identify the tertiary alcohol(s).

 

1. A) only I
2. B) only II
3. C) only III
4. D) both I and III

 

Answer:  C

Difficulty: 1 Easy

Section:  05.04

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  IUPAC Nomenclature of alcohols

 

 

 

12) Identify the tertiary halide(s).

1. A) I and II
2. B) II and III
3. C) III and IV
4. D) only IV

 

Answer:  C

Difficulty: 1 Easy

Section:  05.04

Topic:  Alkyl Halides

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Classify as primary, secondary, or tertiary alkyl halides

 

13) What is the hybridization of the oxygen atom in alcohols?

1. A) sp
2. B) sp2
3. C) sp3

 

Answer:  C

Difficulty: 2 Medium

Section:  05.05

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Physical properties of alcohols

 

 

 

14) The C-O-H bond angle in alcohols is closest to

1. A) 90o.
2. B) 109.5o.
3. C) 120o.
4. D) 180o.

 

Answer:  B

Difficulty: 1 Easy

Section:  05.05

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Physical properties of alcohols

 

15) Which halogen forms the weakest bond to carbon?

1. A) F
2. B) Cl
3. C) Br
4. D) I

 

Answer:  D

Difficulty: 2 Medium

Section:  05.05

Topic:  Alkyl Halides

Bloom’s:  1. Remember

Chapter:  05

Subtopic:  Reactions of alkyl halides

 

16) Which of these five-carbon alcohols would you expect to be most water soluble?

1. A) A
2. B) B
3. C) C
4. D) D

 

Answer:  B

Difficulty: 2 Medium

Section:  05.06

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Physical properties of alcohols

 

17) Rank the following three compounds in order of increasing boiling point.

 

1. CH3CH2CH3II. CH3CH2OH  III. CH3OCH3
2. A) I < II < III
3. B) I < III < II
4. C) II < III < I
5. D) II < I < III

 

Answer:  B

Difficulty: 1 Easy

Section:  05.06

Topic:  Alcohols

Bloom’s:  4. Analyze

Chapter:  05

Subtopic:  Physical properties of alcohols

 

18) What are the products of the following reaction?

 

1. A) 1-bromobutane and water
2. B) 1-bromobutane and hydrogen
3. C) butane and HOBr
4. D) CH3CH2CH2CH2OBr + hydrogen

 

Answer:  A

Difficulty: 2 Medium

Section:  05.07

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  Reactions of alcohols

 

 

 

19) Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide?

1. A) A
2. B) B
3. C) C
4. D) D

 

Answer:  A

Difficulty: 3 Hard

Section:  05.08

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

 

 

20) What is the nucleophile in the following substitution reaction?

 

1. A) A
2. B) B
3. C) C
4. D) D

 

Answer:  C

Difficulty: 2 Medium

Section:  05.08

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

 

 

21) Arrange the following carbocations in order of their decreasing stabilities (most stable first).

 

1. A) I > II > III
2. B) III > II > I
3. C) I > III > II
4. D) II > III > I

 

Answer:  C

Difficulty: 2 Medium

Section:  05.09

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

22) The central carbon of the tert-butyl carbocation, (CH3)3C+, is

1. A) sp2hybridized with a +1 formal charge.
2. B) sp2hybridized with a 0 formal charge.
3. C) sp3hybridized with a +1 formal charge.
4. D) sp3hybridized with a 0 formal charge.

 

Answer:  A

Difficulty: 2 Medium

Section:  05.09

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

 

 

23) What are the C-C-C bond angles in the tert-butyl carbocation, (CH3)3C+?

1. A) 60o
2. B) 90o
3. C) 109.5o
4. D) 120o

 

Answer:  D

Difficulty: 2 Medium

Section:  05.09

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

24) What occurs when an optically active alcohol reacts with HBr to give an alkyl halide?

1. A) incomplete and varying inversion of configuration takes place at the chirality center
2. B) complete inversion of configuration takes place at the chirality center
3. C) the chirality center retains its configuration
4. D) the molecule loses its optical activity

 

Answer:  A

Difficulty: 2 Medium

Section:  05.11

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

25) Which of the following is most reactive with HBr?

1. A) CH3OH
2. B) CH3CH2OH
3. C) (CH3)2CHOH
4. D) (CH3)3COH

 

Answer:  D

Difficulty: 2 Medium

Section:  05.10

Topic:  Alcohols

Bloom’s:  4. Analyze

Chapter:  05

Subtopic:  Reactions of alcohols

 

 

 

26) Arrange the following alcohols in order of their decreasing reactivity with HBr (most reactive first).

1. A) I > II > III
2. B) I > III > II
3. C) III > I > II
4. D) II > III > I

 

Answer:  B

Difficulty: 2 Medium

Section:  05.10

Topic:  Alcohols

Bloom’s:  4. Analyze

Chapter:  05

Subtopic:  Reactions of alcohols

 

 

 

27) If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of HCl, what major product would you expect?

 

1. A) A
2. B) B
3. C) C
4. D) D

 

Answer:  B

Difficulty: 3 Hard

Section:  05.10

Topic:  Alcohols

Bloom’s:  4. Analyze

Chapter:  05

Subtopic:  Reactions of alcohols

 

28) Rank the following alcohols in order of increasing reaction rate with HBr.

 

1. A) II < III < I
2. B) III < II < I
3. C) I < III < II
4. D) I < II < III

 

Answer:  C

Difficulty: 2 Medium

Section:  05.10

Topic:  Alcohols

Bloom’s:  4. Analyze

Chapter:  05

Subtopic:  Reactions of alcohols

 

29) What is the driving force for a carbocation rearrangement to occur?

1. A) the formation of a higher energy, less stable carbocation
2. B) the formation of a higher energy, more stable carbocation
3. C) the formation of a more stable, lower energy carbocation
4. D) the transfer of the positive charge to a less substituted, less stable carbon atom

 

Answer:  C

Difficulty: 2 Medium

Section:  05.12

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

30) Which of the following is not a good method to make bromocyclopentane?

1. A) cyclopentanol plus HBr
2. B) cyclopentanol plus NaBr
3. C) cyclopentanol plus PBr3
4. D) cyclopentane plus Br2with light

 

Answer:  B

Difficulty: 2 Medium

Section:  05.14

Topic:  Alcohols

Bloom’s:  5. Evaluate

Chapter:  05

Subtopic:  Reactions of alcohols

 

31) What is the product of the following reaction?

 

BrCH2CH2CH2CH2OH + SOCl2 →

1. A) ClCH2CH2CH2CH2OH
2. B) BrCH2CH2CH2CH2SH
3. C) BrCH2CH2CH2CH2Cl
4. D) ClCH2CH2CH2CH2SOCl

 

Answer:  C

Difficulty: 2 Medium

Section:  05.14

Topic:  Alcohols

Bloom’s:  3. Apply

Chapter:  05

Subtopic:  Reactions of alcohols

 

 

 

32) Alkyl sulfonates undergo the same type of substitution reactions as alkyl halides and can also be prepared from alcohols. What advantage does the preparation of an alkyl sulfonate from an alcohol have over the preparation of an alkyl halide from an alcohol?

1. A) the preparation of an alkyl sulfonate can be carried out at a much lower temperature and with less expensive reagents
2. B) the configuration at the chirality center in the alcohol is retained in the alkyl sulfonate product and no rearrangements occur
3. C) the alkyl sulfonate product is formed with complete inversion of configuration
4. D) the alkyl sulfonate loses its optical activity and is therefore lower in energy

 

Answer:  B

Difficulty: 2 Medium

Section:  05.15

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols

 

33) Which of the following carbocation rearrangements is likely to occur?

1. A) 2° → 2°
2. B) 2° → 3°
3. C) 3° → 2°
4. D) 2° → 1°

 

Answer:  B

Difficulty: 2 Medium

Section:  05.15

Topic:  Alcohols

Bloom’s:  2. Understand

Chapter:  05

Subtopic:  Reactions of alcohols