Organic Chemistry
Carey/Giuliano
10th edition
Chapter 19
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Question 1
Which compound has the highest boiling point?
A) B)
C) D)
Question 2
Which compound has the lower pKa (i.e., is
more acidic)?
A) B)
C) D)
Question 3
Which one of the following compounds is more
acidic?
A) B)
C) D)
Question 4
Which one of the following compounds has the
highest pKa?
A) B)
C) D)
Question 5
What is the major organic product of the
reaction of propylmagnesium bromide with
CO2 followed by addition of dilute acid?
CH3CH2CH2MgBr + CO2
A) propanoic acid
B) butanoic acid
C) butanol
D) propane
Question 6
Select the product of the reaction of propanoic
acid with thionyl chloride
A) B)
C) D)
Question 7
When benzoic acid reacts with 18O-enriched
methanol (CH318OH), which product will be
obtained?
A) B)
C) D)
Question 8
Which of the following is the thermal
decarboxylation product of the
compound on the right?
A) B)
C) D)
Question 9
What is the IUPAC name of the caboxylic acid
at the right?
A) cis-3-pentenoic acid
B) trans-6-octenoic acid
C) cis-6-octenoic acid
D) trans-6-octenoic acid
Question 10
Which set of reagents would be best to convert
propanol into butanoic acid?
A) Na2Cr2O7, H2SO4
B) PBr3; Mg, diethyl ether; CO2; H3O+
C) HBr; Mg, diethyl ether; H3O+
D) conc. H2SO4, heat; O3; Zn, HCl
Question 11
Compound A has a molecular formula of
C4H8O3. Identify A on the basis of its 1H-
NMR spectra: 1.3 (3H, triplet); 3.6 (2H,
quartet); 4.1 (2H, singlet); 11.1 (1H, broad
singlet).
A) CH3CH2OCH2CO2H
B) CH3OCH2CH2CO2H
C) HOCH2CH2CH2CO2H
D) CH3CH2CO2CH3
Question 12
Compound B has a molecular formula of
C4H8O3. Identify B on the basis of its 1H-
NMR spectra: 2.6 (2H, triplet); 3.4 (3H,
singlet); 3.7 (2H, triplet); 11.3 (1H, broad
singlet).
A) CH3CH2OCH2CO2H
B) HOCH2CH2CH2CO2H
C) CH3OCH2CH2CO2H
D) CH3CH2CO2CH3
Question 13
Which of the following statements is true
regarding the effect of substituents on the
acidity of carboxylic acids?
A) Alkyl substituents have a negligible
effect on acidity.
B) Electron-attracting groups increase
acidity.
C) Substituents on the -carbon increase
acidity.
D) All of the statements above are true.
Question 14
Which of the following reactions proceeds via
an enol intermediate?
A) reaction of butylmagnesium bromide
with benzaldehyde
B) decarboxylation of
CH3CH2CH2CH(CO2H)2 on heating
C) formation of a lactone by cyclization of
5- hydroxypentanoic acid
D) reaction of cyclopentanone with HCN
(NaCH, H+)
Question 15
Rank the following substances in order of
decreasing acid strength (strongest
weakest).
A) 1>2>3
B) 2>3>1
C) 3>2>1
D) 3>1>2
Question 16
If toluene reacts with 1) Br2; then 2) KCN; then
3) H3O+, heat, the product isolated will be:
A) B)
C) D)
Question 17
Which of the following will undergo
decarboxylation on heating?
A) B)
C) D)
Question 18
Which is the correct IUPAC name for the
compound shown?
A) 1,1,3-trimethylpentanoic acid
B) 2,2,4-trimethylpentanoic acid
C) 2,4-dimethyl-2-pentylcarboxylic acid
D) 2,4-dimethyl-2-pentanoic acid
Answer Key – Chapter 19
1. C 11. A
2. B 12. C
3. D 13. D
4. C
14. C
5. B
15. B
6. C
7. C 16. D
8. B 17. C
9. C 18. B
10. B