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Place the following compounds in order of increasing rate of hydrolysis. Place the following compounds in order of increasing rate of hydrolysis. A) I,III,IV,II B) IV,II,III,I C) III,I,II,IV D) I,II,IV,III E) All carboxylic derivatives exhibit similar reactivities with H<sub>2</sub>O.


A) I,III,IV,II
B) IV,II,III,I
C) III,I,II,IV
D) I,II,IV,III
E) All carboxylic derivatives exhibit similar reactivities with H2O.

F) C) and D)
G) All of the above

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In the reaction shown below,which product(s) would be formed? In the reaction shown below,which product(s) would be formed? A) <sup> </sup> B) C) D) E) both A and B


A)
In the reaction shown below,which product(s) would be formed? A) <sup> </sup> B) C) D) E) both A and B
B)
In the reaction shown below,which product(s) would be formed? A) <sup> </sup> B) C) D) E) both A and B
C)
In the reaction shown below,which product(s) would be formed? A) <sup> </sup> B) C) D) E) both A and B
D)
In the reaction shown below,which product(s) would be formed? A) <sup> </sup> B) C) D) E) both A and B
E) both A and B

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

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What would be the other product of the following reaction? What would be the other product of the following reaction? A) <sup> </sup> B) C) D) E)


A)
What would be the other product of the following reaction? A) <sup> </sup> B) C) D) E)
B)
What would be the other product of the following reaction? A) <sup> </sup> B) C) D) E)
C)
What would be the other product of the following reaction? A) <sup> </sup> B) C) D) E)
D)
What would be the other product of the following reaction? A) <sup> </sup> B) C) D) E)
E)
What would be the other product of the following reaction? A) <sup> </sup> B) C) D) E)

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

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What would be the product of the following reaction? What would be the product of the following reaction? A) C<sub>6</sub>H<sub>5</sub>CO<sub>2</sub>H B) C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CO<sub>2</sub>H C) C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>OH D) C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> E) C<sub>6</sub>H<sub>5</sub>CH<sub>3</sub>


A) C6H5CO2H
B) C6H5CH2CO2H
C) C6H5CH2OH
D) C6H5CH2CH2NH2
E) C6H5CH3

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

Correct Answer

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What would be the organic product of the following reaction? (18O is a rare oxygen isotope.) What would be the organic product of the following reaction? (<sup>18</sup>O is a rare oxygen isotope.) A) <sup> </sup> B) C) D) More than one of these. E) None of these.


A)
What would be the organic product of the following reaction? (<sup>18</sup>O is a rare oxygen isotope.) A) <sup> </sup> B) C) D) More than one of these. E) None of these.
B)
What would be the organic product of the following reaction? (<sup>18</sup>O is a rare oxygen isotope.) A) <sup> </sup> B) C) D) More than one of these. E) None of these.
C)
What would be the organic product of the following reaction? (<sup>18</sup>O is a rare oxygen isotope.) A) <sup> </sup> B) C) D) More than one of these. E) None of these.
D) More than one of these.
E) None of these.

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

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Substitutions at sp2 carbons do not occur by an SN2 mechanism,but rather by way of a "tetrahedral intermediate." The tetrahedral intermediate shown could occur in which reaction? Substitutions at sp<sup>2</sup> carbons do not occur by an S<sub>N</sub>2 mechanism,but rather by way of a tetrahedral intermediate. The tetrahedral intermediate shown could occur in which reaction? A) methyl propanoate + ammonia B) propanamide + hydroxide C) propanoic acid + methanol D) propanamide + ethanol E) None of these.


A) methyl propanoate + ammonia
B) propanamide + hydroxide
C) propanoic acid + methanol
D) propanamide + ethanol
E) None of these.

F) All of the above
G) C) and D)

Correct Answer

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What would be the proper name of the following? What would be the proper name of the following? A) 3-nitro-methylbenzoate B) methyl 3-nitrobenzoate C) 3-nitro-methoxybenzoate D) 5-nitro-methylbenzoate E) 3-nitrocarboxymethylbenzene


A) 3-nitro-methylbenzoate
B) methyl 3-nitrobenzoate
C) 3-nitro-methoxybenzoate
D) 5-nitro-methylbenzoate
E) 3-nitrocarboxymethylbenzene

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

Correct Answer

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How many different CH3 signals would you expect in the room-temperature proton NMR spectrum of the molecule below? How many different CH<sub>3</sub> signals would you expect in the room-temperature proton NMR spectrum of the molecule below? A) One B) Two C) Three D) Four E) Five


A) One
B) Two
C) Three
D) Four
E) Five

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

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Rank the following carboxylic acid derivatives in order of decreasing reactivity toward hydrolysis (most reactive on left) : Rank the following carboxylic acid derivatives in order of decreasing reactivity toward hydrolysis (most reactive on left) : A) D > B > A > C B) C > A > B > D C) B > D > A > C D) A > B > D > C E) D > B > C > A


A) D > B > A > C
B) C > A > B > D
C) B > D > A > C
D) A > B > D > C
E) D > B > C > A

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

Correct Answer

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Which of the following would be most likely to result from saponification of a natural triglyceride? Which of the following would be most likely to result from saponification of a natural triglyceride? A) <sup> </sup> B) C) D) E)


A)
Which of the following would be most likely to result from saponification of a natural triglyceride? A) <sup> </sup> B) C) D) E)
B)
Which of the following would be most likely to result from saponification of a natural triglyceride? A) <sup> </sup> B) C) D) E)
C)
Which of the following would be most likely to result from saponification of a natural triglyceride? A) <sup> </sup> B) C) D) E)
D)
Which of the following would be most likely to result from saponification of a natural triglyceride? A) <sup> </sup> B) C) D) E)
E)
Which of the following would be most likely to result from saponification of a natural triglyceride? A) <sup> </sup> B) C) D) E)

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

Correct Answer

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Which functional group has the lowest IR absorption frequency?


A)
Which functional group has the lowest IR absorption frequency? A) B) C) D) E)
B)
Which functional group has the lowest IR absorption frequency? A) B) C) D) E)
C)
Which functional group has the lowest IR absorption frequency? A) B) C) D) E)
D)
Which functional group has the lowest IR absorption frequency? A) B) C) D) E)
E)
Which functional group has the lowest IR absorption frequency? A) B) C) D) E)

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

Correct Answer

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What would account for the fact that the molecule below racemizes easily,despite having three chiral centers? What would account for the fact that the molecule below racemizes easily,despite having three chiral centers? A) Lactones are configurationally unstable B) Molecule loses CO<sub>2</sub> easily C) Enolization occurs easily D) Intramolecular transesterification occurs easily E) This molecule is not chiral.


A) Lactones are configurationally unstable
B) Molecule loses CO2 easily
C) Enolization occurs easily
D) Intramolecular transesterification occurs easily
E) This molecule is not chiral.

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

Correct Answer

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What would be the major expected product from the reaction shown below? What would be the major expected product from the reaction shown below? A) B) C) D) E)


A)
What would be the major expected product from the reaction shown below? A) B) C) D) E)
B)
What would be the major expected product from the reaction shown below? A) B) C) D) E)
C)
What would be the major expected product from the reaction shown below? A) B) C) D) E)
D)
What would be the major expected product from the reaction shown below? A) B) C) D) E)
E)
What would be the major expected product from the reaction shown below? A) B) C) D) E)

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

Correct Answer

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What structure is not an intermediate in the following reaction? What structure is not an intermediate in the following reaction? A) B) C) D) E) None of the above.


A)
What structure is not an intermediate in the following reaction? A) B) C) D) E) None of the above.
B)
What structure is not an intermediate in the following reaction? A) B) C) D) E) None of the above.
C)
What structure is not an intermediate in the following reaction? A) B) C) D) E) None of the above.
D)
What structure is not an intermediate in the following reaction? A) B) C) D) E) None of the above.
E) None of the above.

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

Correct Answer

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Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? A) B) C) D) E)


A)
Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? A) B) C) D) E)
B)
Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? A) B) C) D) E)
C)
Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? A) B) C) D) E)
D)
Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? A) B) C) D) E)
E)
Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine? A) B) C) D) E)

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

Correct Answer

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How can the importance of the following resonance be evaluated? How can the importance of the following resonance be evaluated? A) Charged resonance structures are always more important. B) The C=O IR stretch for amides is significantly different than for other C=O groups. C) The water solubility of amides implicates charged structures. D) The C-N rotational barrier can be determined by NMR. E) More than one of the above are correct.


A) Charged resonance structures are always more important.
B) The C=O IR stretch for amides is significantly different than for other C=O groups.
C) The water solubility of amides implicates charged structures.
D) The C-N rotational barrier can be determined by NMR.
E) More than one of the above are correct.

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

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) <sup> </sup> B) C) mixture of A and B D) None of these. E) No reaction occurs.


A)
What would be the organic product of the following reaction? A) <sup> </sup> B) C) mixture of A and B D) None of these. E) No reaction occurs.
B)
What would be the organic product of the following reaction? A) <sup> </sup> B) C) mixture of A and B D) None of these. E) No reaction occurs.
C) mixture of A and B
D) None of these.
E) No reaction occurs.

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

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Lactones are:


A) Cyclic amides
B) Cyclic anhydrides
C) Cyclic esters
D) Cyclic acids
E) Cyclic ketones

F) All of the above
G) C) and D)

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Predict the product of the following reaction: Predict the product of the following reaction: A) B) C) D) E) None of these.


A)
Predict the product of the following reaction: A) B) C) D) E) None of these.
B)
Predict the product of the following reaction: A) B) C) D) E) None of these.
C)
Predict the product of the following reaction: A) B) C) D) E) None of these.
D)
Predict the product of the following reaction: A) B) C) D) E) None of these.
E) None of these.

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

Correct Answer

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What would be the products of the following reaction? What would be the products of the following reaction? A) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH(CH<sub>3</sub>) + H<sub>2</sub>O B) CH<sub>3</sub>NHC(=O) CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>OH C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CONH<sub>2 </sub> + CH<sub>3</sub>CH<sub>2</sub>OH D) CH<sub>3</sub>OH + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OC(=O) NHCH<sub>3</sub> E) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>NH(CH<sub>3</sub>) COCH<sub>3</sub> + H<sub>2</sub>O


A) CH3CH2CH2CH2NH(CH3) + H2O
B) CH3NHC(=O) CH2CH2CH3 + CH3OH
C) CH3CH2CH2CONH2 + CH3CH2OH
D) CH3OH + CH3CH2CH2OC(=O) NHCH3
E) CH3CH2CH2NH(CH3) COCH3 + H2O

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

Correct Answer

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