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Treatment of a nitrile with a Grignard reagent followed by hydrolysis results in ________.


A) an ester
B) a ketone
C) an aldehyde
D) an ether
E) an alcohol

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

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

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Provide the preferred reagent pair to synthesize 3-ethylpent-2-ene via a Wittig reaction.

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CH3CH2COCH2CH...

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Acetals will react with ________.


A) H3O
B) NaOCH3
C) PhLi
D) CH3CH2MgBr
E) NaBH4

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

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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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Propose a sequence of steps to carry out the following conversion. Propose a sequence of steps to carry out the following conversion.

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1. HOCH2CH2OH, H+
2. Na...

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The double bond between carbon and oxygen is similar to an alkene C=C, except that C=O is:


A) shorter and weaker.
B) shorter and stronger.
C) longer and weaker.
D) longer and stronger.
E) longer.

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

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An ylide is a molecule that can be described as a:


A) carbanion bound to a negatively charged heteroatom.
B) carbocation bound to a positively charged heteroatom.
C) carbocation bound to a carbon radical.
D) carbocation bound to a diazonium ion.
E) carbanion bound to a positively charged heteroatom.

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

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What product will result from the reaction shown? What product will result from the reaction shown?   A)  acetal B)  hydrazine C)  ester D)  ylide E)  ketone


A) acetal
B) hydrazine
C) ester
D) ylide
E) ketone

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

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Provide the major organic product which results when PhCHOHCH3 is treated with PCC.

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Which series of reactions described below will result in the formation of compound A, starting with compound B? Which series of reactions described below will result in the formation of compound A, starting with compound B?   A)  1. HO-(CH<sub>2</sub>) <sub>2</sub>-OH /trace H<sub>3</sub>O<sup>+</sup> 2. DMSO (COCl<sub>2</sub>) /Et<sub>3</sub>N, CH<sub>2</sub>Cl<sub>2</sub> 3)  MgBr-(CH<sub>2</sub>) <sub>2</sub>-CH<sub>3</sub>/diethyl ether 4)  work-up with H<sub>3</sub>O<sup>+</sup> B)  1. PCC 2. SOCl<sub>2</sub> 3)  LiCu-((CH<sub>2</sub>) <sub>2</sub>-CH<sub>3</sub>) <sub>2</sub> 4)  work-up with H<sub>3</sub>O<sup>+</sup> C)  1. Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>/H<sub>2</sub>SO<sub>4</sub> 2. SOCl<sub>2</sub> 3)  2 MgBr-(CH<sub>2</sub>) <sub>2</sub>-CH<sub>3</sub>/diethyl ether 4)  work-up with H<sub>3</sub>O<sup>+</sup> D)  both A and B E)  both B and C


A) 1. HO-(CH2) 2-OH /trace H3O+ 2. DMSO (COCl2) /Et3N, CH2Cl2
3) MgBr-(CH2) 2-CH3/diethyl ether
4) work-up with H3O+
B) 1. PCC 2. SOCl2
3) LiCu-((CH2) 2-CH3) 2
4) work-up with H3O+
C) 1. Na2Cr2O7/H2SO4 2. SOCl2
3) 2 MgBr-(CH2) 2-CH3/diethyl ether
4) work-up with H3O+
D) both A and B
E) both B and C

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

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Oxidation of a 2° alcohol with chromic acid results in the production of ________.


A) an ester
B) a ketone
C) an aldehyde
D) an ether
E) none of the above

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

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