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

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What sequence of reactions is required for the following transformation? What sequence of reactions is required for the following transformation? A) [1] NaOMe,[2] acetone B) [1] Ph<sub>3</sub>P,[2] acetone C) [1] Ph<sub>3</sub>P,[2] KOtBu,[3] acetone D) Acetone,heat


A) [1] NaOMe,[2] acetone
B) [1] Ph3P,[2] acetone
C) [1] Ph3P,[2] KOtBu,[3] acetone
D) Acetone,heat

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

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Name the following aldehyde. Name the following aldehyde. A) 1-Methylcyclopentanal B) 2-Methylcyclopentanal C) 2-Methylcyclopentanecarbaldehyde D) 1-Methylcyclopentanylcarbaldehyde


A) 1-Methylcyclopentanal
B) 2-Methylcyclopentanal
C) 2-Methylcyclopentanecarbaldehyde
D) 1-Methylcyclopentanylcarbaldehyde

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

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Why are strongly acidic conditions not used in the formation of enamines and imines?


A) The carbonyl will be protonated.
B) The amine will be completely protonated.
C) The product is not stable to strong acid.
D) An enol will be formed.

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

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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) A) and C)

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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 D)
F) B) and C)

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

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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) C) and D)

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What is the missing reagent in the reaction below? What is the missing reagent in the reaction below? A) Ethyl amine,mild acid B) Diethylamine,mild acid C) Diethylamine,strong acid D) Diethylamine,NaOMe


A) Ethyl amine,mild acid
B) Diethylamine,mild acid
C) Diethylamine,strong acid
D) Diethylamine,NaOMe

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

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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 B)

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What needs to be done to make the following reaction go to starting materials? What needs to be done to make the following reaction go to starting materials? A) Heat the reaction. B) Add aqueous acid. C) Add aqueous base. D) Add water.


A) Heat the reaction.
B) Add aqueous acid.
C) Add aqueous base.
D) Add water.

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

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Which of the following products is (are) formed by Wittig reaction of CH3CH2CH2CHO with Ph3P CHCH3? Which of the following products is (are) formed by Wittig reaction of CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO with Ph<sub>3</sub>P CHCH<sub>3</sub>? A) Only I B) Only II C) Only III D) Only I and II


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

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

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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 C)
F) A) and D)

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Which is the most reactive carbonyl compound? Which is the most reactive carbonyl compound? 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 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) A) and D)
F) A) and B)

Correct Answer

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What needs to be done to make the following reaction proceed? What needs to be done to make the following reaction proceed? A) Heat the reaction. B) Add an acid catalyst only. C) Add a base catalyst only. D) Heat the reaction and add an acid catalyst.


A) Heat the reaction.
B) Add an acid catalyst only.
C) Add a base catalyst only.
D) Heat the reaction and add an acid catalyst.

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

Correct Answer

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When an aldehyde is reacted with excess ethanol with an acid as a catalyst,what is the product called?


A) Hemiacetal
B) Di-ether
C) Di-alkoxy alkane
D) Acetal

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

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Give the IUPAC name for the following compound. Give the IUPAC name for the following compound. A) R-3-hydroxybutanal B) S-3-hydroxybutanal C) R-2-hydroxybutan-4-al D) S-2-hydroxybutan-4-al


A) R-3-hydroxybutanal
B) S-3-hydroxybutanal
C) R-2-hydroxybutan-4-al
D) S-2-hydroxybutan-4-al

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

Correct Answer

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What would you use to prepare the following ylide from the starting phosphonium salt? What would you use to prepare the following ylide from the starting phosphonium salt? A) Butyl lithium B) 1-Bromo-2-methylpropane C) Triphenylphosphine D) Acetic acid


A) Butyl lithium
B) 1-Bromo-2-methylpropane
C) Triphenylphosphine
D) Acetic acid

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

Correct Answer

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How would the following compounds be distinguishable using IR and 1H NMR spectroscopy? How would the following compounds be distinguishable using IR and <sup>1</sup>H NMR spectroscopy? A) The <sup>1</sup>H NMR spectrum of compound I will have two singlets. B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. C) The <sup>1</sup>H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. D) The <sup>1</sup>H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.


A) The 1H NMR spectrum of compound I will have two singlets.
B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.
C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4.
D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.

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

Correct Answer

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