Question 1

Why can we not prepare a Grignard reagent from a molecule such as 4-bromo-1-butanol?

Accepted Answer

Because Grignard reagents are extremely

Question 2

Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-1-ol and 2-methyl-5-hexyn-1-ol?

Accepted Answer

A)  CrO3 in H2SO4 
B)  Cold conc.H2SO4 
C)  Br2 in CCl4 
D)  NaBH4 
E)  IR spectroscopy 
A)  CrO3 in H2SO4 
B)  Cold conc.H2SO4 
C)  Br2 in CCl4 
D)  NaBH4 
E)  IR spectroscopy

Question 3

Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO ?

Accepted Answer

A)  KMnO4(aq,alkaline) 
B)  CrO3 / H2SO4 
C)  PCC in CH2Cl2 
D)  Br2,CCl4 
E)  Two of the above 
A)  KMnO4(aq,alkaline) 
B)  CrO3 / H2SO4 
C)  PCC in CH2Cl2 
D)  Br2,CCl4 
E)  Two of the above

Question 4

List the following compounds in order of increasing level of oxidation:

Accepted Answer

A)  I,II,III 
B)  III,II,I 
C)  II,I,III 
D)  III,I,II 
E)  I,III,II 
A)  I,II,III 
B)  III,II,I 
C)  II,I,III 
D)  III,I,II 
E)  I,III,II

Question 5

Which of the reagents listed below would efficiently accomplish the transformation of 2-methyl-3-cyclopentenol into 2-methyl-3-cyclopentenone?

Accepted Answer

A)  KMnO4(aq,alkaline) 
B)  CrO3/H2SO4 
C)  H2,Pt 
D)  Br2,CCl4 
E)  Two of the above 
A)  KMnO4(aq,alkaline) 
B)  CrO3/H2SO4 
C)  H2,Pt 
D)  Br2,CCl4 
E)  Two of the above

Question 6

The following transformation would be considered a(n)?

Accepted Answer

A)  reduction 
B)  oxidation 
C)  addition 
D)  elimination 
E)  rearrangement 
A)  reduction 
B)  oxidation 
C)  addition 
D)  elimination 
E)  rearrangement

Question 7

A Grignard reagent will produce a primary alcohol when reacted with _____and_______.

Accepted Answer

formaldehy

Question 8

When 3-methyl-3-pentanol is treated with chromic acid,

Accepted Answer

A)  the color changes from orange to blue. 
B)  the color changes from purple to colorless. 
C)  the purple color remains unchanged. 
D)  the color changes from orange to green. 
E)  the orange color remains unchanged. 
A)  the color changes from orange to blue. 
B)  the color changes from purple to colorless. 
C)  the purple color remains unchanged. 
D)  the color changes from orange to green. 
E)  the orange color remains unchanged.

Question 9

List the following alkyl halides in order of increasing ease of Grignard formation:

Accepted Answer

A)  I,II,III,IV 
B)  III,I,II ,IV 
C)  IV,II,I,III 
D)  III,I,IV,II 
E)  I,IV,III,II 
A)  I,II,III,IV 
B)  III,I,II ,IV 
C)  IV,II,I,III 
D)  III,I,IV,II 
E)  I,IV,III,II

Question 10

NH4Cl is sometimes preferred instead of HCl or H2SO4 for "acid" work-up after Grignard reactions,particularly when the expected and desired product is a tertiary alcohol: why?

Accepted Answer

NH₄Cl provides mildly acidic co

Question 11

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 12

Which combination of reagents is to be preferred for the synthesis of 2,4-dimethylhexane by the Corey-Posner,Whitesides-House procedure?

Accepted Answer

A)  Lithium diisobutylcuprate + sec-butyl bromide 
B)  Lithium dimethylcuprate + 2-bromo-4-methylhexane 
C)  Lithium dimethylcuprate + 4-bromo-2-methylhexane 
D)  Lithium diisopropylcuprate + 1-bromo-2-methylbutane 
E)  Lithium di(2-methylbutyl)cuprate + isopropyl bromide 
A)  Lithium diisobutylcuprate + sec-butyl bromide 
B)  Lithium dimethylcuprate + 2-bromo-4-methylhexane 
C)  Lithium dimethylcuprate + 4-bromo-2-methylhexane 
D)  Lithium diisopropylcuprate + 1-bromo-2-methylbutane 
E)  Lithium di(2-methylbutyl)cuprate + isopropyl bromide

Question 13

What is the product,A,that would be obtained from the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 14

Key to the usefulness of PCC/CH2Cl2 as a selective oxidant for the production of aldehydes from 1 $\degree$ alcohols is___________________.

Accepted Answer

the inability to for

Question 15

Predict the product(s)of the following reaction sequence:

Accepted Answer

A)  A mixture of I and II 
B)  A mixture of I and III 
C)  A mixture of II and III 
D)  A mixture of II and IV 
E)  A mixture of III and IV 
A)  A mixture of I and II 
B)  A mixture of I and III 
C)  A mixture of II and III 
D)  A mixture of II and IV 
E)  A mixture of III and IV

Question 16

Reaction of an alkyllithium with a ketone produces,after acid work-up,a _____________ alcohol.

Accepted Answer

The answer of Reaction of an alkyllithium with a ketone...

Question 17

What is the product,A,that would be obtained from the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 18

What would be the product,D,of the following reaction sequence?

Accepted Answer

A)  2,6-Dimethylheptane 
B)  2,2-Dimethylpropane 
C)  2-Methylpentane 
D)  2,2,5-Trimethylhexane 
E)  2,2,6-Trimethylheptane 
A)  2,6-Dimethylheptane 
B)  2,2-Dimethylpropane 
C)  2-Methylpentane 
D)  2,2,5-Trimethylhexane 
E)  2,2,6-Trimethylheptane

Question 19

List the following compounds in order of increasing level of oxidation:

Accepted Answer

A)  I,II,III 
B)  III,II,I 
C)  II,I,III 
D)  III,I,II 
E)  I,III,II 
A)  I,II,III 
B)  III,II,I 
C)  II,I,III 
D)  III,I,II 
E)  I,III,II

Question 20

A negatively charged hydrogen atom is called a ______________.

Accepted Answer

The answer of A negatively charged hydrogen atom is called...

Exam 12: Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Why can we not prepare a Grignard reagent from a molecule such as 4-bromo-1-butanol?

Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-1-ol and 2-methyl-5-hexyn-1-ol?

Which of the reagents listed below would efficiently accomplish the transformation of CH3CH2CH=CHCH2CH2CH2OH into CH3CH2CH=CHCH2CH2CHO ?

List the following compounds in order of increasing level of oxidation:

Which of the reagents listed below would efficiently accomplish the transformation of 2-methyl-3-cyclopentenol into 2-methyl-3-cyclopentenone?

The following transformation would be considered a(n)?

A Grignard reagent will produce a primary alcohol when reacted with _____and_______.

When 3-methyl-3-pentanol is treated with chromic acid,

List the following alkyl halides in order of increasing ease of Grignard formation:

NH4Cl is sometimes preferred instead of HCl or H2SO4 for "acid" work-up after Grignard reactions,particularly when the expected and desired product is a tertiary alcohol: why?

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

Which combination of reagents is to be preferred for the synthesis of 2,4-dimethylhexane by the Corey-Posner,Whitesides-House procedure?

What is the product,A,that would be obtained from the following reaction sequence?

Key to the usefulness of PCC/CH2Cl2 as a selective oxidant for the production of aldehydes from 1 °\degree° alcohols is___________________.

Predict the product(s)of the following reaction sequence:

Reaction of an alkyllithium with a ketone produces,after acid work-up,a _____________ alcohol.

What is the product,A,that would be obtained from the following reaction sequence?

What would be the product,D,of the following reaction sequence?

List the following compounds in order of increasing level of oxidation:

A negatively charged hydrogen atom is called a ______________.

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 and Ethers

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

Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂CH=CHCH₂CH₂CH₂OH into CH₃CH₂CH=CHCH₂CH₂CHO ?

A Grignard reagent will produce a primary alcohol when reacted with _and___.

NH₄Cl is sometimes preferred instead of HCl or H₂SO₄ for "acid" work-up after Grignard reactions,particularly when the expected and desired product is a tertiary alcohol: why?

Key to the usefulness of PCC/CH₂Cl₂ as a selective oxidant for the production of aldehydes from 1 $\degree$ alcohols is___________________.