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Unformatted text preview: Chapter 4: Alcohols & Alkyl Halides
4-1 What is the IUPAC name of the compound below?
OH 1) 5,5-dimethyl-2-hexanol
4-2 3) 5,5-dimethyl-2-pentanol
4) 2,2-dimethyl-5-pentanol What is the IUPAC name of the compound below?
OH 1) 3-isobutyl-2-hexanol
4-3 3) 2-methyl-5-propyl-6-heptanol
4) 6-methyl-3-propyl-2-heptanol What is the IUPAC name of the compound below?
CH3 CH3 CH3CH2CH2CCH2CH2CHCHCH3
CH(CH3)2 Cl 1) 8-chloro-4-isopropyl-4,7-dimethylnonane
4-4 What is the IUPAC name of the following compound?
CH3 H H OH 1) cis-3-methylcyclohexanol
4-5 3) cis-5-methylcyclohexanol
4) trans-5-methylcyclohexanol Which of the following is isobutyl alcohol?
1) CH3 CH2 CH2 CH2 OH 3) (CH3 )2 CHCH 2 OH 2) CH3 CH2 CH(OH)CH3 4) (CH3 )3 COH 4-6 Identify the tertiary alcohol(s).
CH3CHCH2CH(CH3)2 CH3CH2CHCH(CH3)2 OH OH
A 1) only A
OH B 2) only B 3) only C C 4) both A and C Identify the tertiary halide(s).
CH2Br Br A 1) A and B
4-8 B 2) B and C 2) sp 2) 1090 3) C and D D 4) only D 3) sp2 4) sp3 2) (CH3)3C 3) Br 4) H 3) 1200 4) 1800 Which of the following is the conjugate acid of ethanol?
1) CH3 CH2 O− 4-12 C The COH bond angle in alcohols is closest to:
1) 900 4-11 C Br What is the nucleophile in the following substitution reaction?
(CH3)3COH + HBr
(CH3)3CBr + H2O
1) (CH3)3COH 4-10 H3C What is the hybridization of the oxygen atom in alcohols?
1) sp 4-9 Br H3C 2) CH3 CH2 O+ 3) CH3 CH2 OH 2 + 4) CH3 CH2 OH 3 + What are the products of the following reaction?
CH3CH2CH2CH2OH + HBr
1) 1-bromobutane and water 3) butane and HOBr 2) 1-bromobutane and hydrogen 4) CH3 CH2 CH2 CH2 OBr + hydrogen 4-13 Which of the following is not a good method to make bromocyclopentane?
1) cyclopentanol plus HBr
2) cyclopentanol plus NaBr 4-14 3) cyclopentanol plus PBr3
4) cyclopentane plus Br2 with light Which of the following is most reactive with HBr?
1) CH3 OH
2) CH3 CH2 OH 4-15 3) (CH3 )2 CHOH
4) (CH3 )3 COH Arrange the following alcohols in order of their decreasing reactivity with HBr (most reactive
H3C CH2OH OH CH3
OH A 1) A>B>C
4-16 2) A>C>B B 3) C>A>B CH2 1) A>B>C 2) C>B>A C 4) B>C>A How many monochlorination products do you expect in the following reaction?
(CH3)2CHCH2CH3 1) one 2) two 3) three + Cl2 4) four heat 5) five How many monochlorination products do you expect in the following reaction?
(CH3)2CHCH2CH(CH3)2 + Cl2
1) one 4-19 3) A>C>B CH3 B A 4-18 4) B>C>A Arrange the following carbocations in order of their decreasing stabilities (most stable first).
CH3 4-17 C 2) two 3) three 4) four 5) five Which of the following is the most stable radical? 1) CH3CH2CCH3 2) CH3CH2CCH2 CH3 4-20 3) CH3CHCCH3 CH3 CH3 2Cl B. Cl2 + H 2HCl C. CH4 + Cl D. CH4 + H + CH3
+ HCl + H2
+ E. CH3 + Cl2 CH3Cl F. CH3 + Cl CH3Cl 1) A and C 2) B and F 3) C and D Cl 4) C and E What is the product of the following reaction? BrCH2CH2CH2CH2OH + SOCl2 → 1) ClCH2 CH2 CH2 CH2 OH 3) BrCH2 CH2 CH2 CH2 Cl 2) ClCH2 CH2 CH2 CH2 Cl
4-22 4) ClCH2 CH2 CH2 CH2 SOCl Which constitutional isomer of C6H14 gives only two monochlorination products?
1) 2-methylpentane 3) 2,2-dimethylbutane 2) 3-methylpentane
4-23 4) 2,3-dimethylbutane The central carbon of the tert-butyl carbocation 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. 4-24 CH3 Which of the following are the chain propagating steps in the free radical chlorination of methane?
A. Cl2 4-21 4) CH2CH2CCH3 What are the CCC bond angles in the tert-butyl carbocation?
1) 600 2) 900 3) 109.50 4) 1200 4-25 Studies indicate that the methyl radical is trigonal planar. Based on this, which of the following
best describes the methyl radical?
1) The carbon is sp2 hybridized and the unpaired electron occupies an sp2 orbital.
2) The carbon is sp2 hybridized and the unpaired electron occupies a 2p orbital.
3) The carbon is sp3 hybridized and the unpaired electron occupies an sp3 orbital.
4) The carbon is sp3 hybridized and the unpaired electron occupies a 2p orbital. 4-26 Dibromination of isopropylcyclopentane gives a product which can be isolated in good yields.
Which of the following would you predict to be this product?
+ 2 Br2 BrCH2 CCl4 Br CH2Br
C(CH3)2 C(CH3)2 Br Br
1) 4-27 2) Br 3) 4) Which of the following is the key intermediate in the chlorination reaction below?
cyclopentane + H Cl2 heat chlorocyclopentane H 1) 4-28 CH(CH3)2 2) Cl H
3) 4) Which of the following correctly depicts the protonation of methanol by hydrogen bromide?
1) H3C O H Br 3) H3C H 2) H3C O
H O H Br H Br H H Br 4) H3C O
H Chapter 5: Alkenes & Elimination Reactions
5-1 Carbon-carbon double bonds do not freely rotate like carbon-carbon single bonds. Why?
1) The double bond is much stronger and thus more difficult to rotate.
2) Overlap of the two 2p orbitals of the π bond would be lost.
3) The shorter bond length of the double bond makes it more difficult for the attached
groups to pass each other.
4) Overlap of the sp2 orbitals of the carbon-carbon σ bond would be lost. 5-2 What is the IUPAC name of the following compound? 1) 2,5-dimethyl-1-hexene
5-3 3) 1,4-dimethyl-1-hexene
4) 2,5-dimethyl-5-hexene What is the IUPAC name of the following compound? 1) 2-methyl-3-propyl-2-pentene
5-4 3) 4-ethyl-5-methyl-4-hexene
4) 4-methyl-3-propyl-3-pentene What is the IUPAC name of the following compound?
2) 7-ethyl-2-methyl-6-nonene 5-5 3) 1,1-diethyl-6-methyl-3-heptene
4) 3-ethyl-7-isopropyl-3-octene How many isomeric alkenes of formula C4H8 , including stereoisomers, are possible?
1) one 5-6 2) two 3) three 4) four 5) five How many isomeric alkenes of formula C5H10, including stereoisomers, are possible?
1) three 2) four 3) five 4) six 5) seven 5-7 What is the IUPAC name of the following compound?
Br 1) 3-bromo-2-methylcyclohexene
5-8 3) 6-bromo-1-methylcyclohexene
4) 2-bromo-1-methylcyclohexene What is the IUPAC name of the following compound?
CH2CH2CH3 1) 3-ethyl-5-propyl-1-heptene 3) 4,6-diethyl-1-octene 2) 5-ethyl-3-vinyloctane
5-9 4) 3,5-diethyl-1-octene Which of the following alkenes exhibit E-Z isomerism?
B. (CH3)2C=CHCH3 1) A and B
5-10 2) A and C 4) A, B, and C Which of the following alkenes exhibit E-Z isomerism?
1) only A 5-11 3) B and D C. CH3CH2CH=CHBr
D. H2C=CHCH2CH(CH3)2 2) A and B B. 2-chloropropene
3) B and C 4) A and C What is the IUPAC name of the following compound?
F CH3 1) (E)-3-bromo-1-fluoro-2-methylpropene
4) (Z)-1-bromo-3-fluoro-2-methylpropene C. 3-chloropropene 5-12 Identify the major organic product expected from the acid-catalyzed dehydration of
2) 2-methyl-2-pentene 5-13 3) 3-methyl-1-pentene
4) cis-3-methyl-2-pentene Which alcohol below would undergo acid-catalyzed dehydration most readily?
CH2OH CHCH3 OH CH3
1) 5-14 HO CH3 CH3
2) 3) 4) What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-2propanol?
1) Protonation of the alcohol to form an oxonium ion.
2) Loss of water from the oxonium ion to form a carbocation.
3) Loss of a β-hydrogen from the carbocation to form an alkene.
4) The simultaneous loss of a β-hydrogen and water from the oxonium ion. 5-15 Which of the following carbocations is(are) likely to undergo a rearrangement?
CH3CH2CH2CH2 CH3CHCCH3 CH3
A 1) only A
5-16 2) A and C B 3) B and C C 4) A, B, and C Predict the major product of the following reaction:
1) CH3CH2C=CH2 3) CH3CH=C(CH3)2 2) CH3CH=CHCH2CH3 4) (CH3)2CHCH=CH2 5-17 Which of the following expressions is the experimentally observed rate law for an E2 reaction of
an alkyl halide?
1) rate = k[RX] 3) rate = k[RX] 2 2) rate = k[RX][base] 4) rate = k[base] 5-18 this question.
Disregard Which of the following most readily undergoes an E2 reaction with sodium ethoxide (NaOEt)?
1) tert-butyl fluoride
2) tert-butyl chloride
5-19 3) tert-butyl bromide
4) tert-butyl iodide How many isomeric alkenes are possible, including stereoisomers, in the following reaction?
CH3CH2OH 1) one 2) two 3) three 4) four 5) five 5-20 In the dehydrohalogenation of 2-bromobutane, which conformation below leads directly to the
formation of cis-2-butene?
H3C CH3 Br H3C 1) H 3)
H H H H Br
Br H3C H 2) CH3 H 4)
H CH3 H H 5-21 CH3 CH3
Br Which of the following cannot undergo an E2 reaction?
H3C CH2Br H3C CH2Br Br
CH3 A 1) A 2) B B 3) C CH3 C 4) none (all can undergo an E2 reaction) 5-22 Which of the following would you predict to be the best method for doing the following
conversion with the highest yield?
4) 5-23 H2SO4, heat
(2) KOC(CH3)3 ? This is covered better in Chapter 8. When a strong base is used in the elimination reaction of an alkyl halide the mechanism, in
2) E2 5-24 3) E1 for tertiary halides, E2 for primary and secondary halides
Again, Chapter 8.
4) E2 for tertiary halides, E1 for primary and secondary halides Which of the following sets of conditions most favors the E1 mechanism?
1) When the alkyl halide is tertiary and the base is a weak base.
2) When the alkyl halide is tertiary and the base is a strong base.
3) When the alkyl halide is primary or secondary and the base is a weak base.
4) When the alkyl halide is primary or secondary and the base is a strong base. 5-25 Which of the following would have the fastest rate of reaction to form 4-tert-butylcyclohexene?
Cl 1) (CH3)3C KOC(CH3)3 H
H 2) (CH3)3C KOC(CH3)3 H
Br 3) (CH3)3C KOC(CH3)3 H
H 4) (CH3)3C
H KOC(CH3)3 5-26 What is the first step in the mechanism of the dehydration reaction of a tertiary alcohol with
sulfuric acid to form an alkene?
1) The loss of OH- to form a carbocation.
2) The protonation of the hydroxyl group.
3) The loss of the proton from the hydroxyl group to give an alkoxide ion.
4) The removal of a β-hydrogen from the alcohol. 5-27 Which of the following does not give 1,2-dimethylcyclohexene as one of the acidcatalyzed dehydration products?
CH2OH H3C CH3
1) 5-28 H3C OH H3C CH2OH CH3 2) 3) 4) Including E/Z isomers, how many E2 products are possible in the following reaction?
(CH3)2CHCHCH2CH3 1) one 2) two KOC(CH3)3
(CH3)3COH Br 5-29 CH3
OH 3) three 4) four 5) five Which of the following compounds gives a single E2 product on reaction with sodium ethoxide,
NaOCH 2 CH3 ?
Br H3C CH3 H3C CH3 Br
A 1) A and B
5-30 2) A and C B 3) B and C C 4) A, B, and C Which of the following will give 2-methyl-1-butene as the only alkene product on treatment with
KOC(CH 3)3 in dimethyl sulfoxide?
4) 1-bromo-2-methylbutane 5-31 If the following E2 reaction proceeds through an anti-periplanar transition state, what product or
products are expected?
Cl (CH3)3COH 1) only 3-methylcyclohexene
2) only 1-methylcyclohexene
3) the major product is 3-methylcyclohexene and the minor product is
4) the major product is 1-methylcyclohexene and the minor product is
5-32 Which of the following stereoisomers gives the exclusive E2 product shown.
? CH3CH2OH H3C CH(CH3)2 CH(CH3)2 1) 3)
H3C Cl H3C CH(CH3)2 Cl CH(CH3)2 2) 4)
H3C 5-33 (only E2 product) Cl H3C Cl Zaitsev's rule can be used to predict the major product for which of the following reactions?
1) 2-methylpentane + Br2 (with light)
2) 2-bromo-2-methylpentane + NaOCH2 CH3 (in ethanol) 3) 2-methyl-2-pentanol + PBr3 4) 2-methyl-2-pentanol + HCl 5-34 The acid-catalyzed dehydration of the alcohol shown below gives a major product which
results from a carbocation rearrangement. Identify this major product.
heat CH3 CH3
CH3 1) 5-35 H3C
CH3 2) CH2CH3 CH3 3) 4) Consider the following reaction.
+ RO Na
Br + ROH
I II R = -CH 2 CH3 or -C(CH3 )3
Which statement(s) below is(are) correct?
A. I is the major product based on Zaitsev's rule.
B. The II:I ratio is greater when R = -CH2 CH3 than when R = -C(CH 3 )3 .
C. The II:I ratio is greater when R = -C(CH3 )3 than when R = -CH 2 CH3 .
1) A and B 2) A and C 3) only B 4) only C More of II is formed by the larger base
because it cannot easily access the
central CH2. Chapter 6: Alkene Addition Reactions
6-1 Which of the following is not a metal catalyst for the hydrogenation of an alkene?
1) Pd 6-2 2) Pt 3) Na 4) Ni What is(are) the product(s) in the Pd-catalyzed hydrogenation of
3) a mixture of trans and cis-1,2-dimethylcyclopentane
4) 1,1-dimethylcyclopentane 6-3 Which alkene below is thermodynamically the most stable?
1) 1-hexene 6-4 2) trans-3-hexene 3) cis-3-hexene The stereochemical pathway for the hydrogenation of an alkene with a metal catalyst, such as
platinum, occurs via:
1) syn addition 3) Markovnikov addition 2) anti addition
6-5 4) 2-methyl-2-pentene 4) anti-Markovnikov addition The product(s) in the following reaction is(are):
CH2 H2/Pd H3C 1) only trans-1-4-dimethylcyclohexane
2) only cis-1-4-dimethylcyclohexane
6-6 3) both trans and cis-1-4-dimethylcyclohexane
4) methylcyclohexane What is the major product of the following reaction?
1) 2) 3)
Br 6-7 What is the intermediate in the following reaction?
(CH3)2C=CH2 + HCl
1) H3C C CH3 2) H3C CH3 6-8 Cl C CH2 3) H3C CH3 C CH2Cl 4) H3C CH3 C CH2
CH3 Which of the following is not a possible reaction of a carbocation?
1) addition of a nucleophile
2) rearrangement to a more stable carbocation
3) addition of a proton to form an alkane
4) loss of a β-hydrogen to form an alkene 6-9 Addition of HCl to 3-methyl-1-pentene gives two products. One of these is 2-chloro-3methylpentane. What is the other product?
4) 2-chloro-2-methylpentane 6-10 Predict which of the following alkenes reacts the fastest with HCl?
1) CH3 CH2 CH2 CH2 CH=CH2 3) trans - CH3 CH2 CH=CHCH 2 CH3 2) cis - CH3 CH2 CH=CHCH 2 CH3
6-11 4) ( CH3 )2 C=CHCH 2 CH3 Which species below is the intermediate in the free radical addition of HBr to 1-butene?
1) H3C CH2 CH CH3 3) H3C CH2 CH CH2Br 2) H3C CH2 CH2 CH2 4) H3C CH2 CH CH2
Br 6-12 Which reagent(s) below would work best in converting 2-methyl-2-hexene to 2-methyl-3hexanol?
1) (1) H2 SO4 (2) H2 O 2) 50% H2 SO4 /H2 O 3) (1) BH3 /THF
4) Br2 /H2 O (2) H2 O2 , NaOH 6-13 What is(are) the major product(s) of the following reaction?
1) B2H6, diglyme
2) H2O2, NaOH OH
1) OH 2) 3) 4) both 2 and 3
OH 6-14 What is(are) the product(s) of the following hydroboration-oxidation reaction?
2) H2O2, NaOH 1) 1-methylcyclobutanol
6-15 3) cis-2-methylcyclobutanol
4) equal amounts of 2 and 3 The hydroboration-oxidation reaction can be characterized as the ___________________to an
1) anti-Markovnikov syn addition of water
2) anti-Markovnikov anti addition of water
3) Markovnikov syn addition of water
4) Markovnikov anti addition of water 6-16 What is the major product of the following reaction?
CH3CH2CH2CH C(CH3)2 + Br2
2) 2,2-dibromo-2-methylhexane 6-17 3) 2,3-dibromo-2-methylhexane
4) 2,4-dibromo-2-methylhexane Which of the following alkenes gives 1-bromo-2-methyl-2-pentanol upon reaction with Br2 /H2 O?
1) CH3CH=CHCH(CH3)2 3) CH3CH2CH=C(CH3)2 2) CH3CH2CHCH=CH2 4) CH3CH2CH2C=CH2 CH3 6-18 CH3 Rank the following in order of decreasing reactivity with bromine, Br2 . HOBr CH3 CH3
CH3 CH3 A 2) B>C>A C 3) C>A>B 4) C>B>A Which of the following is least likely to react with an alkene?
1) H3O 6-20 CH3 Attack on the bromonium
ion is hindered by the
methyl groups. B 1) A>B>C
6-19 CH3 + 2) BrCl 3) CH3CH2 (ethyl radical) 4) NaOCH2CH3 Which of the following series of reactions would convert cyclohexanol to 1,2-epoxycyclohexane?
1) (1) NaOCH2CH3 (2) Br2, H2O 2) (1) Br2, light (2) NaOCH2CH3
O 3) (1) H2SO4, heat
4) (1) H2SO4, heat 6-21 (2) CH3COOH, CH3CO2H
(2) O3 Which species below acts as the nucleophile in the acid-catalyzed addition of water to an alkene?
1) H3O 6-22 (3) Zn, H2O + 2) the carbocation - 3) OH 4) H2O Addition of hypobromous acid, HOBr, to 1-methylcyclohexene gives:
1) H Br CH3
3) OH H
OH 6-23 OH OH
CH3 4) H Draw as diequatorial
isomer. CH3 Br A compound, C 15 H24 , is reacted with excess hydrogen using a metal catalyst. One equivalent of
the compound consumed three equivalents of hydrogen. How many rings did the original
compound have? 1) 1 only
6-24 2) 2 only 3) 3 DB, 3 R 4) 2 DB, 4 R 2) 2 only 3) 3 only 4) four only 5) 0 The reaction of 1-butene with bromine, Br2 , in aqueous solution gives primarily 1-bromo-2butanol. Identify the nucleophilic species in the reaction.
1) Br2 6-27 2) 4 DB, 1 R Determine the degrees of unsaturation (sum of double bonds and rings) for a compound with the
formula of C6 H9 BrO.
1) 1 only 6-26 4 DU, 3 C=C
and one ring 4) none A compound, C 20 H30 , can be hydrogenated with platinum metal and hydrogen to give a
compound C20 H38 . How many double bonds (DB) and rings (R) does the original compound
have? (The original compound has no triple bonds.)
1) 4 DB, 2 R 6-25 3) 3 only - 2) Br 3) H2O 4) HOBr A compound is treated with ozone followed by zinc in water to give the following three
products. Which structure below best fits the data?
H3C C H O
CH3 H3C C O O H
H 1) CH3CH=CH(CH2)3CH=C(CH3)2 3) H2C=CCH2CH2C=CHCH3
CH3 2) (CH3)2C=CHCH2CH2CH=CHCH3 CH3 4) H2C=CHCH2CH2C=C(CH3)2
CH3 6-28 Which of the following gives acetone, (CH3 )2 C=O, as one of the products of its ozonolysis? 1) 2) 3) 4) 6-29 Which of the following species is the intermediate in the bromination of propene?
1) H2C CH CH3 Br
2) H2C 3) H2C CH CH3 CH CH3 Br CH3
4) H2C C
H 6-30 A compound, C 7 H13 Cl, is reacted with sodium ethoxide and gives a single elimination product,
C7 H12 . Treatment with ozone followed by zinc and water gives the compound below. Identify
the original compound.
H 1) 2-chloro-1,1-dimethylcyclopentane
6-31 Which of the following correctly depicts the mechanistic first step in the addition of HBr to 2methylpropene
1) (CH3)2C=CH2 Br 3) (CH3)2C=CH2 H Br 2) (CH3)2C=CH2 6-32 H H Br 4) (CH3)2C=CH2 H Br The rearrangement which occurs in the following reaction can be described as a:
3 2 HBr 1 1) hydride shift from C-2 to C-1 3) proton shift from C-2 to C-1 2) hydride shift from C-3 to C-2 4) proton shift from C-3 to C-2 6-33 Which of the following does not give 1-bromo-1-methylcyclopentane as the major product?
HBr 1) HBr
3) ROOR CH3 HO
Br 2 2) CH3
HBr 4) light 6-34 Which point on the potential energy diagram corresponds to the species below for the reaction of
2-methylpropene with hydrogen chloride?
CH3 + δC B
D H3C CH2
H C − Cl δ A
E 1) A
6-35 2) B 3) C 4) D 5) E Identify the nucleophile in the following electrophilic addition reaction.
(CH3)2C=CH2 + CH3CCH2I IN3 N3
- + 1) N3 6-36 + 2) N3 - 3) I 4) I Which of the following is the rate-determining step in the acid-catalyzed addition of water to 2methylpropene?
1) (CH3)2C=CH2 +
2) (CH3)3C + + + + + + H2O (CH3)3C + + H2O
+ + H2O 3) (CH3)3C-OH2
4) (CH3)3 H3O (CH3)3C-OH2
H2O (CH3)3C-OH +
(CH3)2C=CH2 + H3O H3O
+ + 6-37 Which reaction sequence below would work best in converting 3-pentanol into 2,3dibromopentane?
1) (1) H2 SO4 , heat (3) Br 2 , light 2) (1) H2 SO4 , heat (2) H2 /Pt (3) 2 Br 2 , light 3) (1) Br2 , light (2) H2 SO4 , heat (3) H2 /Pt 4) (1) H2 SO4 , heat
6-38 (2) HBr (2) Br2 Which reaction proceeds by anti addition?
Br2/H2O 1) CH3COOH 3) CH3 CH3 CH3 CH3 1) BH3/THF 2) H2/Pt 4) 2) H2O2, NaOH CH3 6-39 O CH3 CH3 Which point on the potential energy diagram corresponds to the carbocation intermediate,
(CH3 )3 C+, for the reaction shown below?
+ H2C=C(CH3)2 + H2O A
+ (CH3)2C=CH2 (CH3)3COH + H + + H2O/H 1) A 2) B 3) C D 4) D 5) E H (cat.) (CH3)3COH 6-40 Which of the following reactions occurs by a two-step mechanism as opposed to a one-step
Cl HCl 1) O
CH3COOH 2) O
Br 3) #3 could also proceed by
an E1 mechanism. NaOCH3
(heat) 4) 6-41 Br NaSH HS What is the product in the following reaction?
6 CH3CH=CH2 + B2H6
1) [(CH3)2CH]3B 3) CH3CH2CH3 2) (CH3CH2CH2)3B 4) polypropylene ...
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