Organic Chemistry
Carey/Giuliano
10th edition
Chapter 15
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Question 1
What starting material would you react with
butyl lithium to make lithium hexanolate
(CH3(CH2)4CH2OLi)?
A) CH3(CH2)4CH2OCH3
B) CH3(CH2)4CH2OH
C) CH3(CH2)4CH2OCH2(CH2)4CH3
D) CH3(CH2)4CH2Br
Question 2
What is the product of the reaction of
ethylmagnesium bromide (CH3CH2MgBr)
with butanal (CH3CH2CH2CH=O) followed by
dilute acid?
A) 2-hexanol
B) 1-butanol
C) 3-hexanol
D) 3-pentanol
Question 3
What is the product of the reaction shown at
the right?
A) B)
C) D)
Question 4
What compound will be obtained from the
reaction shown below?
A) B)
C) D)
Question 5
Which combination of reagents will not
produce 2-phenyl-2-butanol?
A)
B)
C)
D)
Question 6
What is the principal organic product of the
reaction of trans-1-bromo-1-butene with
lithium diethylcuprate?
A) cis-3-hexene
B) trans-3-hexene
C) 3-ethyl-3-hexene
D) trans-2-hexene
Question 7
Which combination of reagents would
accomplish the transformation shown at the
right?
A) CHBr3, KOC(CH3)3, (CH3)3COH
B) CH2Br2, Zn(Cu), ether
C) CH2Br2, KOC(CH3)3, (CH3)3COH
D) CHBr3, NaOH, CH3CH2OH
Question 8
Select the best method to prepare
CH3CH2CCMgI.
A) CH3CH2CCI + Mg (in diethyl ether)
B) CH3CH2CCI3 + Mg(OH)2 (in diethyl
ether)
C) CH3CH2CCH + CH3MgI (in diethyl
ether)
D) CH3CH2CCH + Mg (in diethyl ether)
Question 9
What is the product of the reaction of 1-
bromopropane with lithium in diethyl ether
followed by treatment with copper(I) iodide?
A) CH3CH2CH2CuCH2CH2CH3
B) (CH3CH2CH2)2CuLi
C) (CH3CH2CH2)2CuI
D) CH3CH2CH2CH2CH2CH3
Question 10
What is the main organic product of the
reaction between iodopropane with
magnesium in diethyl ether followed by
treatment with D2O in DCl?
A) CH3CH2CH2Cl
B) CH3CH2CH2OD
C) CH3CH2CH2MgD
D) CH3CH2CH2D
Question 11
Two alcohols, each having the molecular formula
C11H22O, are formed in the reaction of
methylmagnesium bromide with 4-tert-
butylcyclohexanone. These two alcohols are
A) constitutional isomers.
B) enantiomers in equal amounts.
C) enantiomers in unequal amounts.
D) diastereomers.
Question 12
Two alcohols, each having the molecular
formula C7H16O, are formed in the reaction
of methylmagnesium bromide with 3-
hexanone. These two alcohols are
A) constitutional isomers.
B) enantiomers in equal amounts.
C) enantiomers in unequal amounts.
D) diastereomers.
Question 13
Which one of the following is not a suitable
sovent for the reaction shown?
CH3CH2CH2CH2Li + CH3CH=O
CH3CH2CH2CH(OLi)CH3
A) hexane
B) benzene
C) ethanol
D) diethyl ether
Question 14
Which sequence of steps describes the best
synthesis of 1,5-pentanediol
(HOCH2CH2CH2CH2CH2OH)?
A) 1. Cyclopentene + O3;
2. H2O, Zn; 3. NaBH4, H2O
B) 1. 1,4-pentadiene + 2 HCl;
2. NaOH(2 equiv.), heat
C) 1. 4-bromo-1-butanol + Mg (diethyl ether);
2. formaldehyde (CH2=O); 3. H3O+
D) 1. 3-bromo-1-propanol + Mg (diethyl ether);
2. ethylene oxide; 3. H3O+
Question 15
Which (if any) of the following would not be
classified as an organometallic substance?
A) triethylaluminum
B) ethylmagnesium bromide
C) potassium tert-butoxide
D) none of these (all are organometallic
compounds)
Question 16
Rank the following compounds in order of increasing
polarity of the carbon-metal bond
(least to most polar): CH3CH2MgCl, CH3CH2Na,
(CH3CH2)3Al.
A) (CH3CH2)3Al < CH3CH2MgCl < CH3CH2Na
B) CH3CH2Na < CH3CH2MgCl < (CH3CH2)3Al
C) CH3CH2MgCl < (CH3CH2)3Al < CH3CH2Na
D) CH3CH2Na < (CH3CH2)3Al < CH3CH2MgCl
Question 17
What sequence of steps represents the best synthesis of
4-heptanol, (CH3CH2CH2)2CHOH?
A) CH3CH2CH2MgBr (2 moles) + formaldehyde
(CH2=O) in diethyl ether followed by H3O+
B) CH3CH2CH2MgBr + butanal (CH3CH2CH2CH=O)
in diethyl ether followed by H3O+
C) CH3CH2CH2CH2MgBr + acetone [(CH3)2CO] in
diethyl ether followed by H3O+
D) (CH3CH2CH2)2CHMgBr + formaldehyde
(CH2=O) in diethyl ether followed by H3O+
Question 18
Give the major product of the reaction of (E)-2-
pentene with CH2I2 and Zn(Cu).
A) cis-1-ethyl-2-methylcyclopropane
B) trans-1-ethyl-2-methylcyclopropane
C) 1-ethyl-1-methylcyclopropane
D) an equimolar mixture of products A
and B
Question 19
How many signals in the 13C-NMR spectrum
would you expect for the product of the
reaction of propylmagnesium bromide with
formaldehyde (H2C=O) followed by H3O+?
A) 2
B) 3
C) 4
D) 5
Question 20
Which one of the compounds below will be
produced when methylmagnesium bromide
is added to propanoic acid (CH3CH2CO2H)?
A) CH3CH2COCH3
B) CH3CH2CO2-MgBr
C) CH3CH2CH(OH)CH3
D) CH3CH2CH2CH3
Answer Key – Chapter 15
1. D 11. D
2. C 12. B
3. A 13. C
4. B 14. A
5. B 15. C
6. B 16. A
7. A 17. B
8. C 18. B
9. B 19. C
10. D 20. B