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Amides are less basic than amines because:


A) the carbonyl group donates electrons by resonance.
B) the carbonyl group withdraws electrons by resonance.
C) the nitrogen does not have a lone pair of electrons.
D) the nitrogen has a full positive charge.
E) amides do not contain nitrogen.

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

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The hydrolysis of esters, amides, and nitriles:


A) can be carried out under acidic or basic conditions.
B) must be acid-catalyzed.
C) must be base-catalyzed.
D) should be carried out at pH 7.0 for optimum efficiency.
E) is not pH dependent.

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

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Cyclic amides are called:


A) lactones.
B) lactams.
C) aminals.
D) animals.
E) imines.

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

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Provide the structure of propanoic anhydride.

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How might one obtain a significant quantity of a lactone even when the formation reaction has a positive DG?

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This reaction can be driven by...

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Predict the major product of the following reaction. Predict the major product of the following reaction.

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Which of the following are strongly hydrogen bonded in the liquid phase?


A) nitriles
B) esters
C) secondary amides
D) tertiary amides
E) acid chlorides

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

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Provide the major organic product of the following reaction. Provide the major organic product of the following reaction.

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Provide the major organic product in the reaction shown below. Provide the major organic product in the reaction shown below.

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What is the common name for the following carboxylic acid derivative? What is the common name for the following carboxylic acid derivative?   A)  β-hydroxybutyronitrile B)  1-cyano-2-butanol C)  β-hydroxyvaleronitrile D)  γ-hydroxyvaleronitrile E)  2-hydroxypentane nitrile


A) β-hydroxybutyronitrile
B) 1-cyano-2-butanol
C) β-hydroxyvaleronitrile
D) γ-hydroxyvaleronitrile
E) 2-hydroxypentane nitrile

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

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Typically, amides will hydrolyze under ________ conditions than esters.


A) stronger
B) more dilute
C) milder
D) less vigorous
E) more saline

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

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Which of the following compounds is(are) hydrolyzed to butanoic acid upon heating in H2O, H2SO4?


A) ethyl butanoate
B) butyl acetate
C) N-methylbutanamide
D) both A and B
E) both A and C

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

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Provide the major organic product in the reaction shown below. Provide the major organic product in the reaction shown below.

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Using ethanol as your only source of carbon compounds and using any other necessary inorganic reagents, propose a synthesis of ethyl acetate.

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Beginning with ethan...

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What reagent is used to convert pentanamide to 1-pentanamine?


A) POCl3
B) CuCN
C) CH3MgBr
D) SOCl2
E) LiAlH4

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

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Using ethanol as your only source of carbon compounds and using any other necessary inorganic reagents, propose a synthesis of acetonitrile.

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Beginning with ethan...

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Provide the structure of o-bromobenzoyl chloride.

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Using the two key resonance structures for an ester, show how resonance stabilization is lost when an ester is attacked by a nucleophile.

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Predict the major product of the following reaction. Predict the major product of the following reaction.

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Provide the structure of 3-oxobutanenitrile.

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