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Carboxylic acids have unusually high boiling points because:


A) they are significantly heavier than organic molecules with the same molecular weight.
B) they repel each other in the gas phase.
C) they strongly attract each other in the liquid phase.
D) they are usually solids,and solids are not volatile.
E) they exist mostly as ions (RCO2- + H+) and ionic materials are not volatile.

F) All of the above
G) B) and E)

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Which would be the best name of the following compound? Which would be the best name of the following compound? A) 2-bromo-3-isopropylbutenoic acid B) (E) -2-bromo-3,4-dimethyl-2-pentenoic acid C) (E) -2-bromo-3-methyl-2-hexenoic acid D) (E) -2-bromo-3-methyl-2-pentenoic acid E) (Z) -2-bromo-3-methyl-2-pentenoic acid


A) 2-bromo-3-isopropylbutenoic acid
B) (E) -2-bromo-3,4-dimethyl-2-pentenoic acid
C) (E) -2-bromo-3-methyl-2-hexenoic acid
D) (E) -2-bromo-3-methyl-2-pentenoic acid
E) (Z) -2-bromo-3-methyl-2-pentenoic acid

F) A) and B)
G) A) and C)

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Rank the following in decreasing order of acidity (most acidic on left) : Rank the following in decreasing order of acidity (most acidic on left) : A) X > Z > Y B) Y > X > Z C) Z > X > Y D) Z > Y > X E) X > Y > Z


A) X > Z > Y
B) Y > X > Z
C) Z > X > Y
D) Z > Y > X
E) X > Y > Z

F) B) and D)
G) C) and E)

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Which would be the strongest acid of the following?


A) BrCH2CH2CO2H
B) ClCH2CH2CO2H
C) CH3CHClCO2H
D) CF3CO2H
E) CH3CHClCOCl

F) C) and E)
G) D) and E)

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D

Which of the following intermediates are not involved in the acid catalyzed esterification reaction of a carboxylic acid?


A)
Which of the following intermediates are not involved in the acid catalyzed esterification reaction of a carboxylic acid? A) B) C) D) E) All of the above are intermediates.
B)
Which of the following intermediates are not involved in the acid catalyzed esterification reaction of a carboxylic acid? A) B) C) D) E) All of the above are intermediates.
C)
Which of the following intermediates are not involved in the acid catalyzed esterification reaction of a carboxylic acid? A) B) C) D) E) All of the above are intermediates.
D)
Which of the following intermediates are not involved in the acid catalyzed esterification reaction of a carboxylic acid? A) B) C) D) E) All of the above are intermediates.
E) All of the above are intermediates.

F) A) and E)
G) A) and D)

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In the carboxylic acid dimer (below) ,which bond(s) has a strength of about 6-8 kcal/mol? In the carboxylic acid dimer (below) ,which bond(s) has a strength of about 6-8 kcal/mol? A) Bond a B) Bond b C) Bond c D) Bond d E) Bond e


A) Bond a
B) Bond b
C) Bond c
D) Bond d
E) Bond e

F) B) and E)
G) C) and D)

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Which of the following sets of reagents would accomplish the chemical transformation shown? Which of the following sets of reagents would accomplish the chemical transformation shown? A) <sup> </sup> B) C) D) E)


A)
Which of the following sets of reagents would accomplish the chemical transformation shown? A) <sup> </sup> B) C) D) E)
B)
Which of the following sets of reagents would accomplish the chemical transformation shown? A) <sup> </sup> B) C) D) E)
C)
Which of the following sets of reagents would accomplish the chemical transformation shown? A) <sup> </sup> B) C) D) E)
D)
Which of the following sets of reagents would accomplish the chemical transformation shown? A) <sup> </sup> B) C) D) E)
E)
Which of the following sets of reagents would accomplish the chemical transformation shown? A) <sup> </sup> B) C) D) E)

F) None of the above
G) C) and E)

Correct Answer

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What would be the organic product of the following reaction? What would be the organic product of the following reaction? A) CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>H + CO<sub>2</sub> B) 2 CH<sub>3</sub>CO<sub>2</sub>H C) D) E) None of these are formed.


A) CH3CH2CO2H + CO2
B) 2 CH3CO2H
C)
What would be the organic product of the following reaction? A) CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>H + CO<sub>2</sub> B) 2 CH<sub>3</sub>CO<sub>2</sub>H C) D) E) None of these are formed.
D)
What would be the organic product of the following reaction? A) CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>H + CO<sub>2</sub> B) 2 CH<sub>3</sub>CO<sub>2</sub>H C) D) E) None of these are formed.
E) None of these are formed.

F) B) and C)
G) A) and E)

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Several 2-arylpropanoic acids are used as analgesics (painkillers) .Three of these [Ibuprofen (= Advil) ,Naproxen (= Aleve) and Ketoprofen (= Orudis KT) ] are currently available in over-the-counter form.Which of the following sets of reagents would accomplish conversion of an ethyl aromatic to a 2-arylpropanoic acid? Several 2-arylpropanoic acids are used as analgesics (painkillers) .Three of these [Ibuprofen (= Advil) ,Naproxen (= Aleve) and Ketoprofen (= Orudis KT) ] are currently available in over-the-counter form.Which of the following sets of reagents would accomplish conversion of an ethyl aromatic to a 2-arylpropanoic acid? A) B) C) D) E) both A and B


A)
Several 2-arylpropanoic acids are used as analgesics (painkillers) .Three of these [Ibuprofen (= Advil) ,Naproxen (= Aleve) and Ketoprofen (= Orudis KT) ] are currently available in over-the-counter form.Which of the following sets of reagents would accomplish conversion of an ethyl aromatic to a 2-arylpropanoic acid? A) B) C) D) E) both A and B
B)
Several 2-arylpropanoic acids are used as analgesics (painkillers) .Three of these [Ibuprofen (= Advil) ,Naproxen (= Aleve) and Ketoprofen (= Orudis KT) ] are currently available in over-the-counter form.Which of the following sets of reagents would accomplish conversion of an ethyl aromatic to a 2-arylpropanoic acid? A) B) C) D) E) both A and B
C)
Several 2-arylpropanoic acids are used as analgesics (painkillers) .Three of these [Ibuprofen (= Advil) ,Naproxen (= Aleve) and Ketoprofen (= Orudis KT) ] are currently available in over-the-counter form.Which of the following sets of reagents would accomplish conversion of an ethyl aromatic to a 2-arylpropanoic acid? A) B) C) D) E) both A and B
D)
Several 2-arylpropanoic acids are used as analgesics (painkillers) .Three of these [Ibuprofen (= Advil) ,Naproxen (= Aleve) and Ketoprofen (= Orudis KT) ] are currently available in over-the-counter form.Which of the following sets of reagents would accomplish conversion of an ethyl aromatic to a 2-arylpropanoic acid? A) B) C) D) E) both A and B
E) both A and B

F) A) and D)
G) A) and C)

Correct Answer

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Which,if any,of the reactions below would produce 2-methylpropanoic acid?


A)
Which,if any,of the reactions below would produce 2-methylpropanoic acid? A) B) C) D) All of these reactions would produce the desired product. E) None of these reactions would produce the desired product.
B)
Which,if any,of the reactions below would produce 2-methylpropanoic acid? A) B) C) D) All of these reactions would produce the desired product. E) None of these reactions would produce the desired product.
C)
Which,if any,of the reactions below would produce 2-methylpropanoic acid? A) B) C) D) All of these reactions would produce the desired product. E) None of these reactions would produce the desired product.
D) All of these reactions would produce the desired product.
E) None of these reactions would produce the desired product.

F) All of the above
G) A) and E)

Correct Answer

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What would be the name of the following? What would be the name of the following? A) Malonic acid B) Propanoic acid C) Oxalic acid D) Succinic acid E) Butanedioic acid


A) Malonic acid
B) Propanoic acid
C) Oxalic acid
D) Succinic acid
E) Butanedioic acid

F) A) and D)
G) A) and C)

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Rank the following in order of decreasing acidity (more acidic > less acidic) : Rank the following in order of decreasing acidity (more acidic > less acidic) : A) II > III > I > IV > V B) IV > II > I > III > V C) II > IV > I > III > V D) V > III > I > II > IV E) II > IV > I > V > III


A) II > III > I > IV > V
B) IV > II > I > III > V
C) II > IV > I > III > V
D) V > III > I > II > IV
E) II > IV > I > V > III

F) A) and E)
G) A) and D)

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B

Rank the following benzoic acids in order of decreasing acidity: Rank the following benzoic acids in order of decreasing acidity: A) III > I > II B) I > III > II C) II > I > III D) I > II > III E) III > II > I


A) III > I > II
B) I > III > II
C) II > I > III
D) I > II > III
E) III > II > I

F) A) and B)
G) C) and E)

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What major product would result from the following reaction? What major product would result from the following reaction? A) <sup> </sup> B) C) D) E)


A)
What major product would result from the following reaction? A) <sup> </sup> B) C) D) E)
B)
What major product would result from the following reaction? A) <sup> </sup> B) C) D) E)
C)
What major product would result from the following reaction? A) <sup> </sup> B) C) D) E)
D)
What major product would result from the following reaction? A) <sup> </sup> B) C) D) E)
E)
What major product would result from the following reaction? A) <sup> </sup> B) C) D) E)

F) B) and E)
G) A) and D)

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The higher acidity of carboxylic acids compared to other functional groups is best explained by


A) hydrogen bonding.
B) electronegativity of oxygen.
C) water solubility.
D) resonance.
E) electronegativity of carbon.

F) None of the above
G) A) and D)

Correct Answer

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Which compound best fits the following spectroscopic data? 1H NMR = 1.00 (t,J=7.4 Hz,3H) ; 1.65 (sextet,J=7.5 Hz,2H) ; 2.31 (t,J=7.4 Hz,2H) ; and 11.68 (s,1H) ppm.13C NMR = 13.4,18.5,36.3,179.6 ppm.


A)
Which compound best fits the following spectroscopic data? <sup>1</sup>H NMR <font face= symbol ></font> = 1.00 (t,J=7.4 Hz,3H) ; 1.65 (sextet,J=7.5 Hz,2H) ; 2.31 (t,J=7.4 Hz,2H) ; and 11.68 (s,1H) ppm.<sup>13</sup>C NMR <font face= symbol ></font> = 13.4,18.5,36.3,179.6 ppm. A) B) C) D) E) none of the above
B)
Which compound best fits the following spectroscopic data? <sup>1</sup>H NMR <font face= symbol ></font> = 1.00 (t,J=7.4 Hz,3H) ; 1.65 (sextet,J=7.5 Hz,2H) ; 2.31 (t,J=7.4 Hz,2H) ; and 11.68 (s,1H) ppm.<sup>13</sup>C NMR <font face= symbol ></font> = 13.4,18.5,36.3,179.6 ppm. A) B) C) D) E) none of the above
C)
Which compound best fits the following spectroscopic data? <sup>1</sup>H NMR <font face= symbol ></font> = 1.00 (t,J=7.4 Hz,3H) ; 1.65 (sextet,J=7.5 Hz,2H) ; 2.31 (t,J=7.4 Hz,2H) ; and 11.68 (s,1H) ppm.<sup>13</sup>C NMR <font face= symbol ></font> = 13.4,18.5,36.3,179.6 ppm. A) B) C) D) E) none of the above
D)
Which compound best fits the following spectroscopic data? <sup>1</sup>H NMR <font face= symbol ></font> = 1.00 (t,J=7.4 Hz,3H) ; 1.65 (sextet,J=7.5 Hz,2H) ; 2.31 (t,J=7.4 Hz,2H) ; and 11.68 (s,1H) ppm.<sup>13</sup>C NMR <font face= symbol ></font> = 13.4,18.5,36.3,179.6 ppm. A) B) C) D) E) none of the above
E) none of the above

F) A) and E)
G) C) and D)

Correct Answer

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What best accounts for the unusually high boiling points of carboxylic acids relative to other organic compounds of similar molecular weight?


A) The relatively large concentration of oxygen atoms.
B) The presence of intramolecular hydrogen bonding.
C) Carboxylic acids are mostly ionized and thus are mostly ionic compounds.
D) The presence of intermolecular hydrogen bonding.
E) Carboxylic acids do not have unusually high boiling points.

F) B) and C)
G) D) and E)

Correct Answer

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What is the IUPAC name of the following compound? What is the IUPAC name of the following compound? A) 2-hexyl-9-methyldecanoic acid B) 2-isononyloctanoic acid C) 1-methyl-9-carboxypentadecane D) 2-hexyldecanoic acid E) 14-methyl-7-carboxypentadecane


A) 2-hexyl-9-methyldecanoic acid
B) 2-isononyloctanoic acid
C) 1-methyl-9-carboxypentadecane
D) 2-hexyldecanoic acid
E) 14-methyl-7-carboxypentadecane

F) A) and B)
G) A) and C)

Correct Answer

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Which of the following sets of reagents would convert benzyl bromide to phenylethanoic acid? Which of the following sets of reagents would convert benzyl bromide to phenylethanoic acid? A) B) C) D) E) both B and D


A)
Which of the following sets of reagents would convert benzyl bromide to phenylethanoic acid? A) B) C) D) E) both B and D
B)
Which of the following sets of reagents would convert benzyl bromide to phenylethanoic acid? A) B) C) D) E) both B and D
C)
Which of the following sets of reagents would convert benzyl bromide to phenylethanoic acid? A) B) C) D) E) both B and D
D)
Which of the following sets of reagents would convert benzyl bromide to phenylethanoic acid? A) B) C) D) E) both B and D
E) both B and D

F) B) and D)
G) A) and B)

Correct Answer

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E

What reagent(s) would accomplish the following? What reagent(s) would accomplish the following? A) Cl<sub>2</sub>,light B) Cl<sub>2</sub>,H<sub>2</sub>O C) SOCl<sub>2</sub> D) MgCl<sub>2</sub> E) aqueous HCl


A) Cl2,light
B) Cl2,H2O
C) SOCl2
D) MgCl2
E) aqueous HCl

F) B) and C)
G) C) and E)

Correct Answer

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