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What reagent(s) would you use to accomplish the following conversion? What reagent(s) would you use to accomplish the following conversion?   A) CH<sub>3</sub>Br; H<sub>3</sub>O<sup>+</sup> B) CH<sub>3</sub>MgBr; H<sub>3</sub>O<sup>+</sup> C) (CH<sub>3</sub>) <sub>2</sub>CuLi; H<sub>3</sub>O<sup>+</sup> D) CH<sub>3</sub>Br; LiAlH<sub>4</sub>; H<sub>3</sub>O<sup>+</sup> E) LiAlH<sub>4</sub>; CH<sub>3</sub>MgBr; H<sub>3</sub>O<sup>+</sup>


A) CH3Br; H3O+
B) CH3MgBr; H3O+
C) (CH3) 2CuLi; H3O+
D) CH3Br; LiAlH4; H3O+
E) LiAlH4; CH3MgBr; H3O+

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Provide the structure of the compound that results when 4-heptanone is treated with CH3CH=PPh3.

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In the proton NMR spectra of aldehydes and ketones, the protons bonded to carbons adjacent to the carbonyl group typically fall into which of the chemical shift ranges below?


A) 1) 0-2.0 ppm
B) 2) 0-3.0 ppm
C) 4) 0-4.5 ppm
D) 7) 0-8.0 ppm
E) 9) 0-10.0 ppm

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Provide the structure of the compound that results when 4-heptanone is treated with peroxyacetic acid.

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Give the product for the following reaction. Give the product for the following reaction.   A)    B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> E) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH


A) Give the product for the following reaction.   A)    B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> E) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
B) CH3CH2CH3
C) CH3CH2CH2CH2OH
D) CH3CH2CH2CH3
E) CH3CH2CH2OH

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Beginning with sodium acetylide (NaCCH), propose a three-step synthesis of hexanal.

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1) CH3CH2CH2C...

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Provide the major organic product of the reaction of aniline with 3-pentanone.

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In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about ________.


A) 20 ppm
B) 40 ppm
C) 60 ppm
D) 120 ppm
E) 200 ppm

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Provide the proper IUPAC name for PhCH2CH(CH3)CH2CH2CHO.

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4-methyl-5...

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Identify the product for the reaction. Identify the product for the reaction.   A)    B)    C)    D)    E)


A) Identify the product for the reaction.   A)    B)    C)    D)    E)
B) Identify the product for the reaction.   A)    B)    C)    D)    E)
C) Identify the product for the reaction.   A)    B)    C)    D)    E)
D) Identify the product for the reaction.   A)    B)    C)    D)    E)
E) Identify the product for the reaction.   A)    B)    C)    D)    E)

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Provide the structure of the cyanohydrin that results when 4-heptanone is treated with HCN/KCN.

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Draw the two major resonance forms of the cation which results when cyclohexanone's carbonyl group is protonated.

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Diisobutylaluminum hydride (DIBALH) can be used to carry out which of the following conversions?


A) ester to aldehyde
B) carboxylic acid to ester
C) 2 alcohol to ketone
D) aldehyde to carboxylic acid
E) ester to ketone

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Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH2CH2OH)to produce an acetal.

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Give the product for the following reaction. Give the product for the following reaction.   A)    B)    C)    D)    E)


A) Give the product for the following reaction.   A)    B)    C)    D)    E)
B) Give the product for the following reaction.   A)    B)    C)    D)    E)
C) Give the product for the following reaction.   A)    B)    C)    D)    E)
D) Give the product for the following reaction.   A)    B)    C)    D)    E)
E) Give the product for the following reaction.   A)    B)    C)    D)    E)

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Provide the major organic product(s)of the reaction below. Provide the major organic product(s)of the reaction below.

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Name the structure. Name the structure.

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cyclohexan...

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Which of the following compounds is an aldehyde? Which of the following compounds is an aldehyde?   A) I B) II C) III D) IV E) V


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

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Propose a synthesis of 4-phenyl-2-butanol from 3-phenylpropanal.

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Give the systematic name for the structure. Give the systematic name for the structure.   A) 2-methyl-4-hexanone B) 2-methyl-4-heptanone C) 2-methyl-4-pentanone D) 5-methyl-3-hexanone E) 5-methyl-3-heptanone


A) 2-methyl-4-hexanone
B) 2-methyl-4-heptanone
C) 2-methyl-4-pentanone
D) 5-methyl-3-hexanone
E) 5-methyl-3-heptanone

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