Chapter 4 Alcohols and Alkyl Halides: Answers

Prof. Sivaguru Jayaraman

Chapter 4: Alcohols and Alkyl Halides 
1. What is the IUPAC name of the compound below?

A) 5,5-dimethyl-2-hexanol B) 2,2-dimethyl-5-hexanol Ans: A

C) D)

5,5-dimethyl-2-pentanol 2,2-dimethyl-5-pentanol

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

A) 3-isobutyl-2-hexanol B) 2-methyl-5-(1-hydroxyethyl)octane Ans: D

C) D)

2-methyl-5-propyl-6-heptanol 6-methyl-3-propyl-2-heptanol

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

A) B) C) D) Ans:

8-chloro-4-isopropyl-4,7-dimethylnonane 2-chloro-6-isopropyl-3,6-dimethylnonane 2-chloro-3,6,7-trimethyl-6-propyloctane 6-sec-butyl-2-chloro-3,6-dimethyloctane B

4. Rank the following three compounds in order of increasing boiling point. I. CH3CH2CH3 II. CH3CH2OH III. CH3OCH3 A) I < II < III B) I < III < II C) II < III < I D) II < I < III Ans: B

Page 1  Chem 341: Organic Chemistry, Prof. Sivaguru Jayaraman, Fall 2010.

What is the hybridization of the oxygen atom in alcohols? A) sp B) sp2 C) sp3 Ans: C Page 2  Chem 341: Organic Chemistry. Prof. Identify the tertiary alcohol(s). What is the IUPAC name of the following compound? A) cis-3-methylcyclohexanol B) trans-3-methylcyclohexanol Ans: B C) D) cis-5-methylcyclohexanol trans-5-methylcyclohexanol 6.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. (CH3)2CHCH2OH (CH3)3COH A) only I Ans: C B) only II C) only III D) both I and III 8. Sivaguru Jayaraman. Fall 2010. A) I and II Ans: C B) II and III C) III and IV D) only IV 9. Identify the tertiary halide(s). Which of the following is isobutyl alcohol? A) CH3CH2CH2CH2OH C) B) CH3CH2CH(OH)CH3 D) Ans: C 7. Sivaguru Jayaraman 5. .

5o. Which of the following hydrocarbons has the slowest reaction rate with Br2 and light? A) CH4 B) CH3CH2CH3 C) CH3CH2CH2CH3 D) (CH3)3CH Ans: A Page 3  Chem 341: Organic Chemistry. What is the nucleophile in the following substitution reaction? A) A B) B C) C D) D Ans: C 11. Fall 2010. Which one of the following gives a single monochlorination product? A) 2. C) 120o. D) 180o.2-dimethylbutane D) 2-methylpropane Ans: A 15. .Chapter 4 Alcohols and Alkyl Halides: Answers Prof. Assuming the secondary hydrogens in pentane are equally reactive to monochlorination.2-dimethylpropane C) 2. Chlorination of pentane gives a mixture of isomers having the molecular formula C5H11Cl. Rank the following alcohols in order of increasing reaction rate with HBr. Sivaguru Jayaraman 10. Sivaguru Jayaraman. Prof. Ans: B 12. The percentage of 1-chloropentane is 22%.3-dimethylbutane B) 2. A) II < III < I Ans: C B) III < II < I C) I < III < II D) I < II < III 13. The C—O—H bond angle in alcohols is closest to A) 90o. B) 109. what is the percentage of 3-chloropentane in the mixture? A) 48% B) 26% C) 22% D) 14% Ans: B 14.

Sivaguru Jayaraman. Which of the following is not a good method to make bromocyclopentane? A) cyclopentanol plus HBr C) cyclopentanol plus PBr3 B) cyclopentanol plus NaBr D) cyclopentane plus Br2 with light Ans: B 19. II. Fall 2010.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. Which method or methods would work to quantitatively prepare a sodium ethoxide solution? I. CH3CH2OH + NaOH II. . Sivaguru Jayaraman 16. Which of the following is most reactive with HBr? A) CH3OH B) CH3CH2OH C) (CH3)2CHOH D) (CH3)3COH Ans: D 20. What are the products of the following reaction? A) 1-bromobutane and water B) 1-bromobutane and hydrogen Ans: A C) D) butane and HOBr CH3CH2CH2CH2OBr + hydrogen 18. and III Ans: C 17. Arrange the following alcohols in order of their decreasing reactivity with HBr (most reactive first). CH3CH2OH + NaH III. Prof. CH3CH2OH + Na A) I and II B) I and III C) II and III D) I. A) I > II > III Ans: B B) I > III > II C) III > I > II D) II > III > I Page 4  Chem 341: Organic Chemistry.

Sivaguru Jayaraman. Fall 2010. Prof.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. . How many monochlorination products do you expect in the following reaction? A) two Ans: C B) three C) four D) five 23. A) I > II > III Ans: C B) III > II > I C) I > III > II D) II > III > I 22. Arrange the following carbocations in order of their decreasing stabilities (most stable first). Which of the following is the most stable radical? A) A B) B C) C D) D Ans: A Page 5  Chem 341: Organic Chemistry. Sivaguru Jayaraman 21.

3-dimethylbutane Ans: D Page 6  Chem 341: Organic Chemistry. Which constitutional isomer of C6H14 gives only two monochlorination products? A) 2-methylpentane C) 2. Which of the following are the chain propagating steps in the free radical chlorination of methane? A) I and III Ans: D B) II and VI C) III and IV D) III and V 25.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. Prof. Sivaguru Jayaraman. Calculate ΔH° of reaction for the free radical bromination of cyclopentane to give bromocyclopentane. What is the product of the following reaction? BrCH2CH2CH2CH2OH + SOCl2 → A) ClCH2CH2CH2CH2OH B) BrCH2CH2CH2CH2SH Ans: C C) D) BrCH2CH2CH2CH2Cl ClCH2CH2CH2CH2SOCl 26. Fall 2010. . Sivaguru Jayaraman 24.2-dimethylbutane B) 3-methylpentane D) 2. A) –121 kJ/mol Ans: B B) –63 kJ/mol C) +121 kJ/mol D) +63 kJ/mol 27.

Ans: B Page 7  Chem 341: Organic Chemistry. Consider the following reaction (X = Cl or Br). Sivaguru Jayaraman 28. D) The carbon is sp3 hybridized and the unpaired electron occupies a 2p orbital. B) sp2 hybridized with a 0 formal charge. The 2-halopropane to 1-halopropane ratio is the largest when X=Cl. (CH3)3C+. III. is A) sp2 hybridized with a +1 formal charge. C) sp3 hybridized with a +1 formal charge. (CH3)3C+? A) 60o B) 90o C) 109. Sivaguru Jayaraman. Statistically the 1-halopropane should be the major isomer. Studies indicate that the methyl radical is trigonal planar. Which statement(s) is(are) correct? I.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. D) sp3 hybridized with a 0 formal charge.5o D) 120o Ans: D 31. Prof. Ans: A 30. A) only II B) only III C) I and II D) I and III Ans: C 29. Fall 2010. What are the C—C—C bond angles in the tert-butyl carbocation. which of the following best describes the methyl radical? A) The carbon is sp2 hybridized and the unpaired electron occupies an sp2 orbital. Based on this. . C) The carbon is sp3 hybridized and the unpaired electron occupies an sp3 orbital. The central carbon of the tert-butyl carbocation. B) The carbon is sp2 hybridized and the unpaired electron occupies a 2p orbital. The 2-halopropane to 1-halopropane ratio is largest when X=Br. II.

Which of the following would you predict to be this product? A) A B) B C) C D) D Ans: B 33. . Sivaguru Jayaraman. Sivaguru Jayaraman 32. Which of the following is the key intermediate in the chlorination reaction below? A) A B) B C) C D) D Ans: B Page 8  Chem 341: Organic Chemistry.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. Prof. Dibromination of isopropylcyclopentane gives a product which can be isolated in good yields. Fall 2010.

Fall 2010.2-dimethyl-1-butanol Page 9  Chem 341: Organic Chemistry. What is the IUPAC name of the following compound? A) 3-methyl-2-butanol B) 3-methyl-3-butanol Ans: C C) D) 2-methyl-2-butanol 2. The structure below is a generalized abbreviation for which class of compounds? A) ketones B) aldehydes Ans: B C) carboxylic acids D) esters 35. Sivaguru Jayaraman 34. A) ester Ans: A B) ketone C) carboxylic acid D) ether 36. Prof. . Sivaguru Jayaraman. Identify the functional group in the boxed area.Chapter 4 Alcohols and Alkyl Halides: Answers Prof.

Fall 2010.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. Prof. . Which of the following mechanistically depicts the protonation of tert-butyl alcohol by hydrogen bromide? A) A B) B C) C D) D Ans: A 39. How many C3H6Cl2 constitutional isomers do you expect in the dichlorination of propane? A) two B) three C) four D) five Ans: C Page 10  Chem 341: Organic Chemistry. What is the name of the following compound? A) cis-3-methylcyclohexanol B) trans-3-methylcyclohexanol Ans: B C) D) cis-2-methylcyclopentanol trans-3-methylcyclopentanol 38. Sivaguru Jayaraman 37. Sivaguru Jayaraman.

A) A B) B C) C D) D Ans: B Page 11  Chem 341: Organic Chemistry. Sivaguru Jayaraman. What is the major product in the mono-chlorination of pentane? Cl Cl Cl C C C C C A C C C C C B C C C C C C D.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. Sivaguru Jayaraman 40. . the alkane shown would yield C C C C C A) a single monochloride B) two isomeric dichlorides Ans: D C) D) three isomeric monochlorides four isomeric monochlorides 42. Upon free-radical chlorination. Prof. Fall 2010. What is the IUPAC name of the following alcohol? A) trans-4-methylcyclohexanol B) cis-4-methylcyclohexanol Ans: A C) D) trans-3-methylcyclohexanol cis-3-methylcyclohexanol 41. none of these is formed.

The reaction shown below is what type? Cl• + CH4 B) termination HCl + H3C• A) addition Ans: C C) propagation D) initiation 46. If the compound below containing three types of alcohols were exposed to ONLY 1 equivalent of HCl. what major product would you expect? OH 1 HCl ? HOCH2 OH OH OH Cl ClCH2 OH HOCH2 B Cl HOCH2 OH A C D: there is no way to know. Fall 2010. A) A B) B C) C D) D Ans: B 44. Which halogen forms the weakest bond to carbon? A) F B) Cl C) Br D) I Ans: A Page 12  Chem 341: Organic Chemistry. Sivaguru Jayaraman 43. Sivaguru Jayaraman.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. Prof. Which of these five-carbon alcohols would you expect to be most water soluble? OH OH C OH D OH B A A) A B) B C) C D) D Ans: B 45. .

Where would this reaction occur fastest in this molecule? A B Br2 light ? D C A) A B) B C) C D) D Ans: A Page 13  Chem 341: Organic Chemistry. Prof. If you wanted to get the best yield of compound B from compound A. Sivaguru Jayaraman 47. Fall 2010. Sivaguru Jayaraman.Chapter 4 Alcohols and Alkyl Halides: Answers Prof. . you would: ? X compound A compound B A) use chlorine + light rather than bromine + light B) use bromine + light rather than chlorine + light C) neither would give >50% yield D) either would give >50% yield Ans: A 48.

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