Question 1

Name the product which results when 1-methylcyclohexanol is treated with DMP reagent.

Accepted Answer

No reaction occurs;

Question 2

Predict the major product of the following dehydration reaction.

Accepted Answer

@#IMG-DLM& This is a pinacol rearrangeme

Question 3

Which of the following reaction series will result in the formation of a new secondary (2°) alcohol from the beginning alcohol listed at the top?

Accepted Answer

A)  Ethanol
1) Na°
2) CH3CH2I 
B)  t-butyl alcohol
1) K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
C)  2-propanol
1) K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
D)  n-butanol
1) H2SO4/heat
2) Hg(OAc)2 (aq)
3) NaBH4 
E)  2-methylcycloxexanol
1) H2SO4/heat
2) OsO4/H2O2
3) H2SO4/heat 
A)  Ethanol
1) Na°
2) CH3CH2I 
B)  t-butyl alcohol
1) K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
C)  2-propanol
1) K2Cr2O7/acetic acid
2) CH3-MgBr
3) H3O+ 
D)  n-butanol
1) H2SO4/heat
2) Hg(OAc)2 (aq)
3) NaBH4 
E)  2-methylcycloxexanol
1) H2SO4/heat
2) OsO4/H2O2
3) H2SO4/heat

Question 4

Provide the major organic product of the reaction shown.

Accepted Answer

The answer of Provide the major organic product of the...

Question 5

What series of synthetic steps could be used to prepare (CH3)2CHCHO from (CH3)3CH?

Accepted Answer

1) Br₂, hν

Question 6

Provide the name of the major organic product that results when (R)-2-methyl-3-pentanol is heated with conc. H2SO4.

Accepted Answer

Question 7

Which of the following oxidants will convert a primary alcohol to an aldehyde?
1) sodium dichromate /sulfuric acid 3) pyridinium chlorochromate
2) copper oxide 4) dimethylsulfoxide, oxalyl chloride

Accepted Answer

A)  3 & 4 
B)  2, 3, & 4 
C)  3 
D)  1, 2, 3, & 4 
E)  none of the above 
A)  3 & 4 
B)  2, 3, & 4 
C)  3 
D)  1, 2, 3, & 4 
E)  none of the above

Question 8

Provide the structure of the major organic product in the reaction below.
(CH3)3CCH2CH2OH   
→

Accepted Answer

Question 9

Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol) to 4,4-dimethylpentan-2-ol?

Accepted Answer

A)  1. HCl
2) Mg
3) CH3CHO
4) H3O+ 
B)  1. HCl, ZnCl2
2) Mg
3) CH2O
4) H3O+ 
C)  1. SOCl2
2) Mg
3) CH3CHO
4) H3O+ 
D)  1. HCl, ZnCl2
2) Mg
3) CH3CHO
4) H3O+ 
A)  1. HCl
2) Mg
3) CH3CHO
4) H3O+ 
B)  1. HCl, ZnCl2
2) Mg
3) CH2O
4) H3O+ 
C)  1. SOCl2
2) Mg
3) CH3CHO
4) H3O+ 
D)  1. HCl, ZnCl2
2) Mg
3) CH3CHO
4) H3O+

Question 10

Which undergoes dehydration using concentrated H2SO4 faster, cyclopentanol or 1-methylcyclopentanol? Explain briefly.

Accepted Answer

1-methylcyclopentano

Question 11

Provide a mechanism for the reaction shown below.

Accepted Answer

The answer of Provide a mechanism for the reaction shown...

Question 12

What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?

Accepted Answer

A)  sodium (R)-pent-3-oxide 
B)  sodium (S)-pent-2-oxide 
C)  (R)-2-iodopentane 
D)  (S)-2-iodopentane 
E)  none of the above 
A)  sodium (R)-pent-3-oxide 
B)  sodium (S)-pent-2-oxide 
C)  (R)-2-iodopentane 
D)  (S)-2-iodopentane 
E)  none of the above

Question 13

Provide the structure of the major organic product in the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 14

Which alcohol reacts most rapidly with the Lucas reagent?

Accepted Answer

A)  benzyl alcohol 
B)  methanol 
C)  2-propanol 
D)  isobutanol 
A)  benzyl alcohol 
B)  methanol 
C)  2-propanol 
D)  isobutanol

Question 15

What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol?
1) PCC
2) CH3CH2CH2MgBr
3) H3O+
or

Accepted Answer

1) HBr or

Question 16

Provide the major organic product of the following.

Accepted Answer

The answer of Provide the major organic product of the...

Question 17

Provide the name of the major organic product that results when trans-4-methylcyclohexanol is treated with thionyl chloride.

Accepted Answer

cis-1-chlo

Question 18

What is the major organic product when n-butanol reacts with hydrochloric acid?

Accepted Answer

The answer of What is the major organic product when...

Question 19

Provide the name of the major organic product that results when cyclopentanol is treated with acetyl chloride.

Accepted Answer

The answer of Provide the name of the major organic...

Question 20

What reagents are necessary for the following conversion?

Accepted Answer

1) Na₂Cr₂O₇ /

Exam 11: Reactions of Alcohols

Name the product which results when 1-methylcyclohexanol is treated with DMP reagent.

Predict the major product of the following dehydration reaction.

Which of the following reaction series will result in the formation of a new secondary (2°) alcohol from the beginning alcohol listed at the top?

Provide the major organic product of the reaction shown.

What series of synthetic steps could be used to prepare (CH3)2CHCHO from (CH3)3CH?

Provide the name of the major organic product that results when (R)-2-methyl-3-pentanol is heated with conc. H2SO4.

Which of the following oxidants will convert a primary alcohol to an aldehyde? 1) sodium dichromate /sulfuric acid 3) pyridinium chlorochromate 2) copper oxide 4) dimethylsulfoxide, oxalyl chloride

Provide the structure of the major organic product in the reaction below. (CH3)3CCH2CH2OH →

Which set of reagents will best convert 2,2-dimethylpropan-1-ol (neopentyl alcohol) to 4,4-dimethylpentan-2-ol?

Which undergoes dehydration using concentrated H2SO4 faster, cyclopentanol or 1-methylcyclopentanol? Explain briefly.

Provide a mechanism for the reaction shown below.

What compound is produced when (R)-pentan-2-ol is treated with TsCl followed by NaI?

Provide the structure of the major organic product in the reaction below.

Which alcohol reacts most rapidly with the Lucas reagent?

What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol? 1) PCC 2) CH3CH2CH2MgBr 3) H3O+ or

Provide the major organic product of the following.

Provide the name of the major organic product that results when trans-4-methylcyclohexanol is treated with thionyl chloride.

What is the major organic product when n-butanol reacts with hydrochloric acid?

Provide the name of the major organic product that results when cyclopentanol is treated with acetyl chloride.

What reagents are necessary for the following conversion?

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

Structure and Synthesis 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

What series of synthetic steps could be used to prepare (CH₃)₂CHCHO from (CH₃)₃CH?

Provide the name of the major organic product that results when (R)-2-methyl-3-pentanol is heated with conc. H₂SO₄.

Provide the structure of the major organic product in the reaction below. (CH₃)₃CCH₂CH₂OH →

Which undergoes dehydration using concentrated H₂SO₄ faster, cyclopentanol or 1-methylcyclopentanol? Explain briefly.

What series of synthetic steps could be used to prepare hexan-3-ol from propan-1-ol? 1) PCC 2) CH₃CH₂CH₂MgBr 3) H₃O⁺ or