Question 1

Reduction of a ketone with NaBH4 will result in the formation of ________.

Accepted Answer

A)  a primary alcohol 
B)  an alkene 
C)  a secondary alcohol 
D)  an alkane 
E)  an aldehyde 
A)  a primary alcohol 
B)  an alkene 
C)  a secondary alcohol 
D)  an alkane 
E)  an aldehyde

Question 2

A novice chemist wished to prepare 1-methylcyclohexane-1,4-diol from the keto alcohol shown below by treating it with the appropriate Grignard reagent. Was the chemist successful? Explain.

Accepted Answer

No, the novice chemist was not

Question 3

Complete the following reaction by providing a structure for the necessary starting material.

Accepted Answer

The answer of Complete the following reaction by providing a...

Question 4

Explain how a mixture of phenol and cyclopentanol might be separated using differences in their solubility properties.

Accepted Answer

Dissolve the mixture in an organic solve

Question 5

What is synthesis gas and what commercially important alcohol is prepared from it?

Accepted Answer

Synthesis gas is a mixture of

Question 6

Provide an acceptable name for the compound below.

Accepted Answer

(Z)-4-meth

Question 7

What sequence of reagents is needed to convert benzyl bromide into 1-phenyl-2-octanol?

Accepted Answer

1) Mg, eth

Question 8

Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?

Accepted Answer

A)  BrCH2CH2CH2CN 
B)  CH3COCH2CH2Br 
C)  (CH3)2NCH2CH2Br 
D)  H2NCH2CH2Br 
E)  all of the above 
A)  BrCH2CH2CH2CN 
B)  CH3COCH2CH2Br 
C)  (CH3)2NCH2CH2Br 
D)  H2NCH2CH2Br 
E)  all of the above

Question 9

Phenol is more acidic than cyclohexanol because of the resonance stabilization of the phenoxide ion. Draw the proton transfer reaction that take place between sodium hydroxide and phenol. Then show the resonance structures that can be drawn for the phenoxide ion.

Accepted Answer

The answer of Phenol is more acidic than cyclohexanol because...

Question 10

Provide a detailed step-by-step mechanism that would account for the formation of the product in the following reaction.

Accepted Answer

The answer of Provide a detailed step-by-step mechanism that would...

Question 11

Provide a detailed, stepwise mechanism for the reaction of acetyl chloride (CH3COCl) and 2 equivalents of PhMgCl.

Accepted Answer

Question 12

How would one used a Grignard-based synthesis to accomplish the following transformation?
benzyl bromide (PhCH2Br) to 3-phenylpropan-1-ol

Accepted Answer

1) Mg, Et₂O

Question 13

The reaction of what two compounds produces n-butyllithium?

Accepted Answer

1-bromobut

Question 14

What combination of reagents can be used in a Grignard-based synthesis of 1-propylcyclohexanol?

Accepted Answer

cyclohexan

Question 15

What reagent(s) are needed to complete the following reaction?

Accepted Answer

A)  1) LiAlH4, 2) H3O+ 
B)  1) NaBH4, 2) H3O+ 
C)  H2, Pd 
D)  1) DIBAL-H, 2) H3O+ 
A)  1) LiAlH4, 2) H3O+ 
B)  1) NaBH4, 2) H3O+ 
C)  H2, Pd 
D)  1) DIBAL-H, 2) H3O+

Question 16

Which series of reactions would best facilitate the following conversion?

Accepted Answer

A)  1. KMnO4 (aq)
2) Hg(OAc)2 (aq)
3) NaBH4/OH- 
B)  1. NaBH4
2) H3PO4/Δ 
C)  1. H3C-MgBr
2) H2O/H3O+ 
D)  1. NaBH4
2) HBr (g)
3) Mg/ether
4) H2O/H3O+ 
E)  1. Raney nickel
2) H3C-MgBr
3) H2O/H3O+ 
A)  1. KMnO4 (aq)
2) Hg(OAc)2 (aq)
3) NaBH4/OH- 
B)  1. NaBH4
2) H3PO4/Δ 
C)  1. H3C-MgBr
2) H2O/H3O+ 
D)  1. NaBH4
2) HBr (g)
3) Mg/ether
4) H2O/H3O+ 
E)  1. Raney nickel
2) H3C-MgBr
3) H2O/H3O+

Question 17

Provide the structure of the major organic product in the reaction below.
CH3CH2CH(CH3)CH2CO2CH3   
→

Accepted Answer

Question 18

________, commonly used in automobile antifreezes, is a diol which is highly toxic if ingested.

Accepted Answer

Ethylene g

Question 19

Provide the structure of the major organic product in the reaction shown below.
CH3CH2CH2CHO   
→

Accepted Answer

Question 20

Predict the major organic product in the reaction shown below.
ethyl magnesium chloride + pent-1-yne

Accepted Answer

ethane + C

Exam 10: Structure and Synthesis of Alcohols

Reduction of a ketone with NaBH4 will result in the formation of ________.

A novice chemist wished to prepare 1-methylcyclohexane-1,4-diol from the keto alcohol shown below by treating it with the appropriate Grignard reagent. Was the chemist successful? Explain.

Complete the following reaction by providing a structure for the necessary starting material.

Explain how a mixture of phenol and cyclopentanol might be separated using differences in their solubility properties.

What is synthesis gas and what commercially important alcohol is prepared from it?

Provide an acceptable name for the compound below.

What sequence of reagents is needed to convert benzyl bromide into 1-phenyl-2-octanol?

Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?

Phenol is more acidic than cyclohexanol because of the resonance stabilization of the phenoxide ion. Draw the proton transfer reaction that take place between sodium hydroxide and phenol. Then show the resonance structures that can be drawn for the phenoxide ion.

Provide a detailed step-by-step mechanism that would account for the formation of the product in the following reaction.

Provide a detailed, stepwise mechanism for the reaction of acetyl chloride (CH3COCl) and 2 equivalents of PhMgCl.

How would one used a Grignard-based synthesis to accomplish the following transformation? benzyl bromide (PhCH2Br) to 3-phenylpropan-1-ol

The reaction of what two compounds produces n-butyllithium?

What combination of reagents can be used in a Grignard-based synthesis of 1-propylcyclohexanol?

What reagent(s) are needed to complete the following reaction?

Which series of reactions would best facilitate the following conversion?

Provide the structure of the major organic product in the reaction below. CH3CH2CH(CH3)CH2CO2CH3 →

________, commonly used in automobile antifreezes, is a diol which is highly toxic if ingested.

Provide the structure of the major organic product in the reaction shown below. CH3CH2CH2CHO →

Predict the major organic product in the reaction shown below. ethyl magnesium chloride + pent-1-yne

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Reduction of a ketone with NaBH₄ will result in the formation of ________.

Provide a detailed, stepwise mechanism for the reaction of acetyl chloride (CH₃COCl) and 2 equivalents of PhMgCl.

How would one used a Grignard-based synthesis to accomplish the following transformation? benzyl bromide (PhCH₂Br) to 3-phenylpropan-1-ol

Provide the structure of the major organic product in the reaction below. CH₃CH₂CH(CH₃)CH₂CO₂CH₃ →

Provide the structure of the major organic product in the reaction shown below. CH₃CH₂CH₂CHO →