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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) C) and D)

Correct Answer

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What is the structure of benzophenone? What is the structure of benzophenone?   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) None of the above

Correct Answer

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

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 D)
F) A) and C)

Correct Answer

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What compound is consistent with the following 1H NMR spectrum? What compound is consistent with the following <sup>1</sup>H NMR spectrum?   A) Acetone B) Propanal C) Cyclobutanone D) 2-butanone


A) Acetone
B) Propanal
C) Cyclobutanone
D) 2-butanone

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

Correct Answer

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Identify how you could synthesize an enamine.


A) React a ketone or an aldehyde with a secondary amine.
B) React a ketone or an aldehyde with a primary amine.
C) React a ylide with a primary amine.
D) React a ylide with a secondary amine.

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

Correct Answer

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What is the missing reagent in the reaction below? What is the missing reagent in the reaction below?   A) I B) II C) III D) IV


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

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

Correct Answer

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C

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) B) and D)
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) None of the above
F) All of the above

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) B) and C)

Correct Answer

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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) None of the above
F) C) and D)

Correct Answer

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D

Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone?


A) An aldehyde has a C-H stretch (one or two) between 2700-2830 cm-1.
B) An aldehyde has a proton signal between 9-10 ppm.
C) A ketone has signals around 2-3 ppm.
D) A ketone has a signal around 200 ppm.

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

Correct Answer

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What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde? What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?   A) I B) II C) III D) IV


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

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

Correct Answer

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

Correct Answer

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

Correct Answer

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B

What is the major organic product obtained from the following sequence of reactions? What is the major organic product obtained from 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)

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

Correct Answer

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Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except


A) aqueous acid.
B) aqueous base.
C) oxidizing reagents.
D) reducing reagents.

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

Correct Answer

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