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Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum? Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

Correct Answer

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What is the driving force for the Wittig reaction?


A) The formation of an alkene
B) The deprotonation of a phosphonium salt
C) The elimination of triphenylphosphine oxide
D) The formation of a phosphonium salt

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

Correct Answer

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What is the product of the following reaction? What is the product of the following reaction?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

Correct Answer

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What is the structure of 3-methylcyclohexanone? What is the structure of 3-methylcyclohexanone?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

Correct Answer

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What is the product of the following sequence of reactions? What is the product of the following sequence of reactions?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

Correct Answer

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Which of the following oxidants would work for the following reaction? Which of the following oxidants would work for the following reaction?   A) H<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub> B) FeCl<sub>3</sub> C) I<sub>2</sub> D) Ag<sub>2</sub>O


A) H2Cr2O7
B) FeCl3
C) I2
D) Ag2O

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

Correct Answer

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Is the following reaction reversible and, if so, under what conditions? Is the following reaction reversible and, if so, under what conditions?   A) No B) Yes, under acidic conditions C) Yes, using Pd/C D) Yes, under basic conditions


A) No
B) Yes, under acidic conditions
C) Yes, using Pd/C
D) Yes, under basic conditions

E) B) and D)
F) A) and C)

Correct Answer

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Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde?


A) A ketone has no carbonyl stretch at 1720 cm-1.
B) An aldehyde has a carbonyl stretch at 1820 cm-1.
C) An aldehyde has two C-H stretches between 2700-2850 cm-1.
D) A ketone has no C-H stretches.

E) C) and D)
F) A) and B)

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What is the missing reagent in the reaction below? What is the missing reagent in the reaction below?   A) Methanol, acid B) Ethanol, acid C) NaOEt D) NaOMe


A) Methanol, acid
B) Ethanol, acid
C) NaOEt
D) NaOMe

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

Correct Answer

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Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone?


A) Because the Grignard reagent will react with the acid and be quenched
B) Because the ketone will be protonated and thus unreactive
C) Because the ketone will form an unreactive enol
D) Because the Grignard reagent won't dissolve in aqueous solutions

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

Correct Answer

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Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C.What accounts for this difference in boiling points?


A) Butanol is polar while butanal is not polar.
B) Butanol can exhibit dipole-dipole interactions while butanal cannot.
C) Butanol can hydrogen bond and butanal cannot hydrogen bond.
D) Butanal is less sterically hindered than butanol.

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

Correct Answer

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What product is formed when the following acetal is hydrolyzed with aqueous acid? What product is formed when the following acetal is hydrolyzed with aqueous acid?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

Correct Answer

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What is the product of the following reaction? What is the product of the following reaction?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) C) and D)
F) A) and B)

Correct Answer

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What is (are) the product(s) of the following reaction? What is (are)  the product(s)  of the following reaction?   A) I only B) II only C) III only D) II and III


A) I only
B) II only
C) III only
D) II and III

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

Correct Answer

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What is the IUPAC for the following compound? What is the IUPAC for the following compound?   A) 1-Formyl-2-nitropropane B) 1-Formyl-3-nitrobutane C) 2-Nitrobutanal D) 3-Nitrobutanal


A) 1-Formyl-2-nitropropane
B) 1-Formyl-3-nitrobutane
C) 2-Nitrobutanal
D) 3-Nitrobutanal

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

Correct Answer

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Which is the most reactive carbonyl compound?


A) I
B) II
C) III
D) IV

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

Correct Answer

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What is (are) the product(s) of the following reaction? What is (are)  the product(s)  of the following reaction?   A) I only B) II only C) III only D) II and III


A) I only
B) II only
C) III only
D) II and III

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

Correct Answer

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Which of the following statements about carbohydrates is not true?


A) Carbohydrates are sugars and starches.
B) Carbohydrates often contain acetals and hemiacetals.
C) In solution, glucose is in the cyclic acetal form only.
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde.

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

Correct Answer

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What is the product of the following reaction? What is the product of the following reaction?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

Correct Answer

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What product is formed when the following compound is hydrolyzed with aqueous acid? What product is formed when the following compound is hydrolyzed with aqueous acid?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

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

Correct Answer

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