Question 1

Which of the following would not react with either Na2Cr2O7 or pyridinium chlorochromate?

Accepted Answer

A) only 1 
B) only 3 
C) only 2 and 4 
D) 1,2,3 and 4 
A) only 1 
B) only 3 
C) only 2 and 4 
D) 1,2,3 and 4 A

Question 2

Addition of chlorotrimethylsilane to an alcohol

Accepted Answer

A) results in an SN1 reaction. 
B) requires acidic reaction conditions. 
C) is sterically hindered by the three methyl groups. 
D) results in the formation of an ether. 
E) produces a more reactive species. 
A) results in an SN1 reaction. 
B) requires acidic reaction conditions. 
C) is sterically hindered by the three methyl groups. 
D) results in the formation of an ether. 
E) produces a more reactive species. D

Question 3

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

Accepted Answer

A) tert-butyl phenyl ether 
B) isopropyl methyl ether 
C) anisole 
D) tert-butyl methyl ether 
A) tert-butyl phenyl ether 
B) isopropyl methyl ether 
C) anisole 
D) tert-butyl methyl ether A

Question 4

Instructions: Consider the Grignard reaction below to answer the following question(s).
 
-Refer to instructions.If a secondary alcohol were desired as a product of the reaction,B should be replaced with

Accepted Answer

A) an ester 
B) an aldehyde 
C) formaldehyde (methanal) 
D) a primary alcohol 
A) an ester 
B) an aldehyde 
C) formaldehyde (methanal) 
D) a primary alcohol

Question 5

Which of the following are ethers?

Accepted Answer

A) only 1 and 2 
B) only 1 and 4 
C) only 1,2 and 3 
D) all of these are ethers 
A) only 1 and 2 
B) only 1 and 4 
C) only 1,2 and 3 
D) all of these are ethers

Question 6

Instructions: To answer the following question(s),consider the reaction below.
 
-Refer to instructions.Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary,secondary,or tertiary.

Accepted Answer

(R)-heptan

Question 7

Which of the following is not a property of a protecting group?

Accepted Answer

A) change the reactivity of a functional group 
B) inert to reaction conditions 
C) becomes a permanent part of the product 
D) alters the mechanism of the desired reaction 
E) all of these are properties of a protecting group 
A) change the reactivity of a functional group 
B) inert to reaction conditions 
C) becomes a permanent part of the product 
D) alters the mechanism of the desired reaction 
E) all of these are properties of a protecting group

Question 8

Instructions: To answer the following question(s),consider the reaction below. 
-Refer to instructions.The conversion of an alcohol into an alkyl chloride by reaction with SOCl2 is an example of:

Accepted Answer

A) an E1 process 
B) an SN1 process 
C) an E2 process 
D) an SN2 process 
A) an E1 process 
B) an SN1 process 
C) an E2 process 
D) an SN2 process

Question 9

Instructions: To answer the following question(s),consider the reaction below.
Refer to instructions.The alcohol product is classified as a:

Accepted Answer

A) 1$\circ$ alcohol 
B) 2$\circ$ alcohol 
C) 3$\circ$ alcohol 
D) 4$\circ$ alcohol 
A) 1$\circ$ alcohol 
B) 2$\circ$ alcohol 
C) 3$\circ$ alcohol 
D) 4$\circ$ alcohol

Question 10

What is the IUPAC name of the following compound?

Accepted Answer

A) cyclohexen-3-ol 
B) cyclohexen-2-ol 
C) cyclohex-1-en-3-ol 
D) cyclohex-2-en-1-ol 
A) cyclohexen-3-ol 
B) cyclohexen-2-ol 
C) cyclohex-1-en-3-ol 
D) cyclohex-2-en-1-ol

Question 11

Instructions: Provide correct IUPAC names for each of the structures below.

-Name:

Accepted Answer

m-chloroanisole or m

Question 12

Instructions: To answer the following question(s),consider the reaction below. 
-Refer to instructions.Provide the IUPAC name for the product alcohol.

Accepted Answer

trans-2-me

Question 13

Instructions: Provide correct IUPAC names for each of the structures below.

-Name:

Accepted Answer

1-ethoxy-2,2-dimethy

Question 14

The following IR spectrum would most likely be associated with
 
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology,11-01-08)

Accepted Answer

A) phenol 
B) aromatic alcohol 
C) aliphatic alcohol 
D) ether 
E) cannot determine from the isolated spectrum 
A) phenol 
B) aromatic alcohol 
C) aliphatic alcohol 
D) ether 
E) cannot determine from the isolated spectrum

Question 15

Which of the following is probably the least useful in IR characterization of a compound?

Accepted Answer

A) phenol: 3500 cm-1 
B) alcohol: 3500 cm-1 
C) phenol: 1500-1600 cm-1 
D) ether: 1050-1150 cm-1 
E) all of these are about equally useful 
A) phenol: 3500 cm-1 
B) alcohol: 3500 cm-1 
C) phenol: 1500-1600 cm-1 
D) ether: 1050-1150 cm-1 
E) all of these are about equally useful

Question 16

What is the IUPAC name of the following compound?

Accepted Answer

A) ethyl isopropyl thiol 
B) 2-methylsulfanylpropane 
C) ethyl isopropyl disulfide 
D) ethyl isopropyl sulfide 
A) ethyl isopropyl thiol 
B) 2-methylsulfanylpropane 
C) ethyl isopropyl disulfide 
D) ethyl isopropyl sulfide

Question 17

Instructions: Consider the reaction below to answer the following question.

-Refer to instructions.Mechanistically,the Williamson ether synthesis outlined above is:

Accepted Answer

A) an E1 process 
B) an SN1 process 
C) an E2 process 
D) an SN2 process 
A) an E1 process 
B) an SN1 process 
C) an E2 process 
D) an SN2 process

Question 18

What is the best choice of reagent to achieve the following transformation?

Accepted Answer

A) CrO3,H3O+,acetone 
B) pyridium chlorochromate,CH2Cl2 
C) SOCl2,pyridine 
D) NaBH4,H3O+ 
E) LiAlH4,H3O+ 
A) CrO3,H3O+,acetone 
B) pyridium chlorochromate,CH2Cl2 
C) SOCl2,pyridine 
D) NaBH4,H3O+ 
E) LiAlH4,H3O+

Question 19

What is the IUPAC name of the following compound?

Accepted Answer

A) cis-4-methylcyclohexanol 
B) trans-4-methylcyclohexanol 
C) cis-4-hydroxy-1-methylcyclohexane 
D) trans-4-hydroxy-1-methylcyclohexane 
A) cis-4-methylcyclohexanol 
B) trans-4-methylcyclohexanol 
C) cis-4-hydroxy-1-methylcyclohexane 
D) trans-4-hydroxy-1-methylcyclohexane

Exam 13: Alcohols,phenols,and Thiols: Ethers and Sulfides

Which of the following would not react with either Na2Cr2O7 or pyridinium chlorochromate?

Addition of chlorotrimethylsilane to an alcohol

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

Instructions: Consider the Grignard reaction below to answer the following question(s). -Refer to instructions.If a secondary alcohol were desired as a product of the reaction,B should be replaced with

Which of the following are ethers?

Instructions: To answer the following question(s),consider the reaction below. -Refer to instructions.Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary,secondary,or tertiary.

Which of the following is not a property of a protecting group?

Instructions: To answer the following question(s),consider the reaction below. -Refer to instructions.The conversion of an alcohol into an alkyl chloride by reaction with SOCl2 is an example of:

Instructions: To answer the following question(s),consider the reaction below. Refer to instructions.The alcohol product is classified as a:

What is the IUPAC name of the following compound?

Instructions: Provide correct IUPAC names for each of the structures below. -Name:

Instructions: To answer the following question(s),consider the reaction below. -Refer to instructions.Provide the IUPAC name for the product alcohol.

Instructions: Provide correct IUPAC names for each of the structures below. -Name:

The following IR spectrum would most likely be associated with Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology,11-01-08)

Which of the following is probably the least useful in IR characterization of a compound?

What is the IUPAC name of the following compound?

Instructions: Consider the reaction below to answer the following question. -Refer to instructions.Mechanistically,the Williamson ether synthesis outlined above is:

What is the best choice of reagent to achieve the following transformation?

What is the IUPAC name of the following compound?

Structure and Bonding

Polar Covalent Bonds: Acids and Bases

Organic Compounds: Alkanes and Their Stereochemistry

Organic Compounds: Cycloalkanes and Their Stereochemistry

Stereochemistry at Tetrahedral Centers

An Overview of Organic Reactions

Alkenes and Alkynes

Reactions of Alkenes and Alkynes

Aromatic Compounds

Structure Determination: Mass Spectrometry,infrared Spectroscopy,and Ultraviolet Spectroscopy

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Organohalides: Nucleophilic Substitutions and Eliminations

Aldehydes and Ketones: Nucleophilic Addition Reactions

Carboxylic Acids and Nitriles

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution and Condensation Reactions

Amines and Heterocycles

Biomolecules: Amino Acids,peptides,and Proteins

Amino Acid Metabolism

Biomolecules: Carbohydrates

Carbohydrate Metabolism

Biomolecules: Lipids and Their Metabolism

Biomolecules: Nucleic Acids and Their Metabolism

Filters

Which of the following would not react with either Na₂Cr₂O₇ or pyridinium chlorochromate?

Instructions: To answer the following question(s),consider the reaction below. -Refer to instructions.The conversion of an alcohol into an alkyl chloride by reaction with SOCl₂ is an example of: