Organic Chemistry 10th Edition by Francis Carey - Test Bank

Organic Chemistry 10th Edition by Francis Carey – Test Bank

 

Instant Download – Complete Test Bank With Answers

 

 

Sample Questions Are Posted Below

 

 

1. What is the IUPAC name of the compound below?

 

 

 

 

 

 

 

 

A.5,5-dimethyl-2-hexanol

 

B.2,2-dimethyl-5-hexanol

C.5,5-dimethyl-2-pentanol

1. 2,2-dimethyl-5-pentanol

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

2. What is the IUPAC name of the compound below?

 

 

 

 

 

 

 

 

1. 3-isobutyl-2-hexanol

 

B.2-methyl-5-(1-hydroxyethyl)octane

C.2-methyl-5-propyl-6-heptanol

D.6-methyl-3-propyl-2-heptanol

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

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

 

 

 

 

 

 

 

 

 

 

 

1. 8-chloro-4-isopropyl-4,7-dimethylnonane

 

1. 2-chloro-6-isopropyl-3,6-dimethylnonane

 

1. 2-chloro-3,6,7-trimethyl-6-propyloctane

 

1. 6-sec-butyl-2-chloro-3,6-dimethyloctane

 

 

 

 

 

 

 

 

 

 

 

 

4.

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.02

 

Subtopic: IUPAC nomenclature of alkyl halides

 

Topic: Alkyl Halides

 

 

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

 

 

1. CH₃CH₂CH₃ CH₃CH₂OH III. CH₃OCH₃

 

 

 

1. I< II < III

 

1. I < III < II

 

1. II < III < I

 

1. II < I < III

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 4. Analyze

 

Chapter: 05

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.06

 

Subtopic: Physical properties of alcohols

 

Topic: Alcohols

 

5. What is the IUPAC name of the following compound?

 

 

 

 

 

 

 

 

 

 

 

1. cis-3-methylcyclohexanol

 

B.trans-3-methylcyclohexanol

C.cis-5-methylcyclohexanol

1. trans-5-methylcyclohexanol

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

6. Which of the following is isobutyl alcohol?

 

1. CH₃CH₂CH₂CH₂OH

 

B.CH₃CH₂CH(OH)CH₃

C.(CH₃)₂CHCH₂OH

1. (CH₃)₃COH

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

7. Identify the tertiary alcohol(s).

 

 

 

 

 

 

 

 

 

 

 

 

1. only I

 

1. only II

 

1. only III

 

1. both I and III

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.04

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

8. Identify the tertiary halide(s).

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. I and II

 

1. II and III

 

1. III and IV

 

1. only IV

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.04

 

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

 

Topic: Alkyl Halides

 

9. What is the hybridization of the oxygen atom in alcohols?

 

1. sp

 

1. sp²

 

1. sp³

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Physical properties of alcohols

 

Topic: Alcohols

 

10. What is the nucleophile in the following substitution reaction?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. A

 

1. B

 

1. C

 

1. D

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

 

 

 

 

 

 

 

 

 

 

 

 

11. The C-O-H bond angle in alcohols is closest to

 

1. 90^o.
2. 5^o.
3. 120^o.
4. 180^o.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Physical properties of alcohols

 

Topic: Alcohols

 

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

 

 

 

 

 

 

 

 

1. II < III < I

 

1. III < II < I

 

1. I < III < II

 

1. I < II < III

 

 

 

 

 

 

 

 

 

13. What is the driving force for a carbocation rearrangement to occur?

 

1. the formation of a higher energy, less stable carbocation

 

1. the formation of a higher energy, more stable carbocation

 

1. the formation of a more stable, lower energy carbocation

 

1. the transfer of the positive charge to a less substituted, less stable carbon atom

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Bloom’s Level: 4. Analyze Chapter: 05 Difficulty: Medium Gradable: automatic Section: 05.10

 

Subtopic: Reactions of alcohols Topic: Alcohols

 

 

 

 

 

 

 

 

 

Accessibility: Keyboard Navigation Bloom’s Level: 2. Understand Chapter: 05 Difficulty: Medium Gradable: automatic Section: 05.12

 

Subtopic: Reactions of alcohols Topic: Alcohols

 

14. What are the products of the following reaction?

 

 

 

 

 

 

 

A.1-bromobutane and water

 

B.1-bromobutane and hydrogen

C.butane and HOBr

1. CH₃CH₂CH₂CH₂OBr + hydrogen

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.07

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

15. Which of the following is not a good method to make bromocyclopentane?

 

1. cyclopentanol plus HBr

 

B.cyclopentanol plus NaBr

C.cyclopentanol plus PBr₃

1. cyclopentane plus Br₂ with light

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 5. Evaluate

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.14

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

16. Which of the following is most reactive with HBr?

 

1. CH₃OH

 

1. CH₃CH₂OH
2. (CH₃)₂CHOH
3. (CH₃)₃COH

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 4. Analyze

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.10

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

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

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. I > II > III

 

1. I > III > II

 

1. III > I > II

 

1. II > III > I

 

Bloom’s Level: 4. Analyze

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.10

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

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

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. I > II > III

 

1. III > II > I

 

1. I > III > II

 

1. II > III > I

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

 

19. What is the product of the following reaction? BrCH₂CH₂CH₂CH₂OH + SOCl₂ →

 

 

1. ClCH₂CH₂CH₂CH₂OH

 

B.BrCH₂CH₂CH₂CH₂SH

C.BrCH₂CH₂CH₂CH₂Cl

1. ClCH₂CH₂CH₂CH₂SOCl

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.14

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

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

 

1. sp² hybridized with a +1 formal charge.
2. sp² hybridized with a 0 formal charge.
3. sp³ hybridized with a +1 formal charge.
4. sp³ hybridized with a 0 formal charge.

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

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

 

1. 60^o
2. 90^o
3. 5^o
4. 120^o

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.09

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

22. The structure below is a generalized abbreviation for which class of compounds?

 

 

 

 

 

 

 

 

 

 

1. ketones

 

1. aldehydes

 

1. carboxylic acids

 

1. esters

 

Bloom’s Level: 1. Remember

 

Chapter: 05

 

Difficulty: Easy

 

Gradable: automatic

 

Section: 05.01

 

Subtopic: C=O containing functional groups

 

Topic: Functional Groups

 

23. 23_. Identify the functional group in the boxed area.

 

 

 

 

 

 

 

 

 

 

 

 

 

1. ester

 

1. ketone

 

1. carboxylic acid

 

1. ether

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.01

 

Subtopic: C=O containing functional groups

 

Topic: Functional Groups

 

24. 24_. What is the IUPAC name of the following compound?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. 3-methyl-2-butanol

 

B.3-methyl-3-butanol

C.2-methyl-2-butanol

D.2,2-dimethyl-1-butanol

 

 

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

25. 25_. What is the name of the following compound?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. cis-3-methylcyclohexanol

 

1. cis-2-methylcyclopentanol

 

1. trans-3-methylcyclohexanol

 

1. trans-3-methylcyclopentanol

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

26. 26_. Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. A

 

1. B

 

1. C

 

1. D

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.08

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

27. 27_. What is the IUPAC name of the following alcohol?

 

 

 

 

 

 

 

 

 

 

 

 

 

1. trans-4-methylcyclohexanol

 

1. trans-3-methylcyclohexanol

 

1. cis-4-methylcyclohexanol

 

1. cis-3-methylcyclohexanol

 

Bloom’s Level: 3. Apply

 

Chapter: 05

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.03

 

Subtopic: IUPAC Nomenclature of alcohols

 

Topic: Alcohols

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

28. If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of HCl, what majorproduct would you expect?

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1. A

 

1. B

 

1. C

 

1. D

 

Bloom’s Level: 4. Analyze

 

Chapter: 05

 

Difficulty: Hard

 

Gradable: automatic

 

Section: 05.10

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

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

 

 

 

 

 

 

 

 

 

 

 

1. A

 

1. B

 

1. C

 

1. D

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.06

 

Subtopic: Physical properties of alcohols

 

Topic: Alcohols

 

30. Which halogen forms the weakest bond to carbon?

 

1. F

 

1. Cl

 

1. Br

 

1. I

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 1. Remember

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.05

 

Subtopic: Reactions of alkyl halides

 

Topic: Alkyl Halides

 

31. What occurs when an optically active alcohol reacts with HBr to give an alkyl halide?

 

1. incomplete and varying inversion of configuration takes place at the chirality center

 

1. complete inversion of configuration takes place at the chirality center

 

1. the chirality center retains its configuration

 

1. the molecule loses its optical activity

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.11

 

Subtopic: Reactions of alcohols

 

Topic: 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. the preparation of an alkyl sulfonate can be carried out at a much lower temperature and with less expensive reagents

 

1. the configuration at the chirality center in the alcohol is retained in the alkyl sulfonate product and no rearrangements occur

 

1. the alkyl sulfonate product is formed with complete inversion of configuration

 

1. the alkyl sulfonate loses its optical activity and is therefore lower in energy

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.15

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

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

 

1. 2° → 2°

 

 

1. 2° → 3°

 

 

C.3° → 2°

 

 

D.2° → 1°

 

 

 

Accessibility: Keyboard Navigation

 

Bloom’s Level: 2. Understand

 

Chapter: 05

 

Difficulty: Medium

 

Gradable: automatic

 

Section: 05.15

 

Subtopic: Reactions of alcohols

 

Topic: Alcohols

 

Category	# of Questions
Accessibility: Keyboard Navigation	14
Bloom’s Level: 1. Remember	2
Bloom’s Level: 2. Understand	15
Bloom’s Level: 3. Apply	10
Bloom’s Level: 4. Analyze	5
Bloom’s Level: 5. Evaluate	1
Chapter: 05	33
Difficulty: Easy	5
Difficulty: Hard	4
Difficulty: Medium	24
Gradable: automatic	33
Section: 05.01	2
Section: 05.02	1
Section: 05.03	7
Section: 05.04	2
Section: 05.05	3
Section: 05.06	2
Section: 05.07	1
Section: 05.08	2
Section: 05.09	3
Section: 05.10	4
Section: 05.11	1
Section: 05.12	1
Section: 05.14	2
Section: 05.15	2
Subtopic: C=O containing functional groups	2
Subtopic: Classify as primary, secondary, or tertiary alkyl halides	1
Subtopic: IUPAC Nomenclature of alcohols	8
Subtopic: IUPAC nomenclature of alkyl halides	1
Subtopic: Physical properties of alcohols	4
Subtopic: Reactions of alcohols	16
Subtopic: Reactions of alkyl halides	1
Topic: Alcohols	28
Topic: Alkyl Halides	3
Topic: Functional Groups	2