Question 1

What is the product of the reaction of propyl alcohol with (CH3)3SiCl in the presence of a tertiary amine?

Accepted Answer

A)  CH3CH2CH2Si(CH3)3 
B)  (CH3)2CHSi(CH3)3 
C)  CH3CH2CH2OSi(CH3)3 
D)  (CH3)2CHOSi(CH3)3 
E)  (CH3CH2CH2)3SiOH 
A)  CH3CH2CH2Si(CH3)3 
B)  (CH3)2CHSi(CH3)3 
C)  CH3CH2CH2OSi(CH3)3 
D)  (CH3)2CHOSi(CH3)3 
E)  (CH3CH2CH2)3SiOH C

Question 2

Propose a mechanism for the following transformation:

Accepted Answer

The answer of Propose a mechanism for the following transformation:...

Question 3

Which of the following statements is NOT true of ethers?

Accepted Answer

A)  Ethers are generally unreactive molecules toward reagents other than strong acids. 
B)  Ethers generally have lower boiling points than alcohols of a corresponding molecular weight. 
C)  Ethers generally have much lower water solubilities than alcohols with a corresponding molecular weight. 
D)  Ethers can generally be cleaved by heating them with strong acids. 
E)  Ethers form peroxides when allowed to stand in the presence of oxygen. 
A)  Ethers are generally unreactive molecules toward reagents other than strong acids. 
B)  Ethers generally have lower boiling points than alcohols of a corresponding molecular weight. 
C)  Ethers generally have much lower water solubilities than alcohols with a corresponding molecular weight. 
D)  Ethers can generally be cleaved by heating them with strong acids. 
E)  Ethers form peroxides when allowed to stand in the presence of oxygen. C

Question 4

Which of the following could be used to synthesize 1-bromopentane?

Accepted Answer

A)  CH3CH2CH2CH=CH2 + HBr$\rightarrow$ 
B)  CH3CH2CH2CH2CH2OH + PBr3 $\rightarrow$ 
C)  CH3CH2CH2CH2CH2OH + NaBr $\rightarrow$ 
D)  CH3CH2CH2CH2CH2OH + Br2 $\rightarrow$ 
E)  CH3CH2CH2CH=CH2 + Br2$\rightarrow$ 
A)  CH3CH2CH2CH=CH2 + HBr$\rightarrow$ 
B)  CH3CH2CH2CH2CH2OH + PBr3 $\rightarrow$ 
C)  CH3CH2CH2CH2CH2OH + NaBr $\rightarrow$ 
D)  CH3CH2CH2CH2CH2OH + Br2 $\rightarrow$ 
E)  CH3CH2CH2CH=CH2 + Br2$\rightarrow$

Question 5

Give the correct IUPAC name corresponding to the following structure:

Accepted Answer

(R)-3-ethy

Question 6

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 7

Propose a mechanism for the following transformation:

Accepted Answer

The answer of Propose a mechanism for the following transformation:...

Question 8

If trans-2-butene is treated with meta-chloroperbenzoic acid what is the final product?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above

Question 9

Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

Accepted Answer

A)  CH3CH2CH2CH2CH3 
B)  CH3CH2CH2CH2OH 
C)  CH3CH2CH2OCH3 
D)  CH3CH2CH2Cl 
E)  CH3CH2OCH2CH3 
A)  CH3CH2CH2CH2CH3 
B)  CH3CH2CH2CH2OH 
C)  CH3CH2CH2OCH3 
D)  CH3CH2CH2Cl 
E)  CH3CH2OCH2CH3

Question 10

Which reagent(s)would transform propyl alcohol into propyl bromide?

Accepted Answer

A)  Concd.HBr and heat 
B)  PBr3 
C)  NaBr/H2O and heat 
D)  More than one of these 
E)  All of these 
A)  Concd.HBr and heat 
B)  PBr3 
C)  NaBr/H2O and heat 
D)  More than one of these 
E)  All of these

Question 11

Which of the alcohols listed below would you expect to react most rapidly with HBr?

Accepted Answer

A)  CH3CH2CH2CH2CH2CH2OH 
B)  (CH3CH2)2CH2CH2OH 
C)  (CH3CH2)2CHOHCH3 
D)  CH3CH2CH2CH2CH2OH 
E)  (CH3CH2)2C(CH3)OH 
A)  CH3CH2CH2CH2CH2CH2OH 
B)  (CH3CH2)2CH2CH2OH 
C)  (CH3CH2)2CHOHCH3 
D)  CH3CH2CH2CH2CH2OH 
E)  (CH3CH2)2C(CH3)OH

Question 12

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 13

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 14

Which of the following could be used to synthesize 2-bromobutane?

Accepted Answer

A)  CH3CH2CH$ \equiv$CH2 + Br2 (aq)$\rightarrow$ 
B)  CH3CH2C$ \equiv$CH3 + HBr $\rightarrow$ 
C)  CH3CH2C$ \equiv$CH + HBr $\rightarrow$ 
D)  CH3CH2C$ \equiv$CH + Br2 $\rightarrow$ 
E)  More than one of the above 
A)  CH3CH2CH$ \equiv$CH2 + Br2 (aq)$\rightarrow$ 
B)  CH3CH2C$ \equiv$CH3 + HBr $\rightarrow$ 
C)  CH3CH2C$ \equiv$CH + HBr $\rightarrow$ 
D)  CH3CH2C$ \equiv$CH + Br2 $\rightarrow$ 
E)  More than one of the above

Question 15

When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl chloride (SOCl2)in the presence of a 3° amine,the resulting alkyl chloride is produced with _____________ of configuration.

Accepted Answer

Question 16

The number of secondary alcohols corresponding to the formula C5H12O,counting stereoisomers separately,is:

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5

Question 17

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

The answer of Complete the following reaction sequence,giving structural details...

Question 18

The following reaction,   is probably:

Accepted Answer

A)  an SN1-type reaction involving the protonated alcohol as the substrate. 
B)  an SN2-type reaction involving the protonated alcohol as the substrate. 
C)  an E1-type reaction involving the protonated alcohol as the substrate. 
D)  an E2-type reaction involving the protonated alcohol as the substrate. 
E)  an epoxidation reaction. 
A)  an SN1-type reaction involving the protonated alcohol as the substrate. 
B)  an SN2-type reaction involving the protonated alcohol as the substrate. 
C)  an E1-type reaction involving the protonated alcohol as the substrate. 
D)  an E2-type reaction involving the protonated alcohol as the substrate. 
E)  an epoxidation reaction.

Question 19

What is the total number of pentyl alcohols,including stereoisomers?

Accepted Answer

A)  7 
B)  8 
C)  9 
D)  10 
E)  11 
A)  7 
B)  8 
C)  9 
D)  10 
E)  11

Question 20

Draw all of the enantiomeric forms corresponding to the formula C5H12O.

Accepted Answer

Exam 11: Alcohols and Ethers

What is the product of the reaction of propyl alcohol with (CH3)3SiCl in the presence of a tertiary amine?

Propose a mechanism for the following transformation:

Which of the following statements is NOT true of ethers?

Which of the following could be used to synthesize 1-bromopentane?

Give the correct IUPAC name corresponding to the following structure:

Complete the following reaction sequence,giving structural details of all key intermediates:

Propose a mechanism for the following transformation:

If trans-2-butene is treated with meta-chloroperbenzoic acid what is the final product?

Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

Which reagent(s)would transform propyl alcohol into propyl bromide?

Which of the alcohols listed below would you expect to react most rapidly with HBr?

Complete the following reaction sequence,giving structural details of all key intermediates:

Complete the following reaction sequence,giving structural details of all key intermediates:

Which of the following could be used to synthesize 2-bromobutane?

When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl chloride (SOCl2)in the presence of a 3° amine,the resulting alkyl chloride is produced with _____________ of configuration.

The number of secondary alcohols corresponding to the formula C5H12O,counting stereoisomers separately,is:

Complete the following reaction sequence,giving structural details of all key intermediates:

The following reaction, is probably:

What is the total number of pentyl alcohols,including stereoisomers?

Draw all of the enantiomeric forms corresponding to the formula C5H12O.

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

What is the product of the reaction of propyl alcohol with (CH₃)₃SiCl in the presence of a tertiary amine?

When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl chloride (SOCl₂)in the presence of a 3° amine,the resulting alkyl chloride is produced with _____________ of configuration.

The number of secondary alcohols corresponding to the formula C₅H₁₂O,counting stereoisomers separately,is:

Draw all of the enantiomeric forms corresponding to the formula C₅H₁₂O.