Question 1

Rearrangements are likely to occur in which of the following reaction types?

Accepted Answer

A)  SN1 reactions 
B)  SN2 reactions 
C)  E1 reactions 
D)  E2 reactions 
E)  Both SN1 and E1 reactions 
A)  SN1 reactions 
B)  SN2 reactions 
C)  E1 reactions 
D)  E2 reactions 
E)  Both SN1 and E1 reactions

Question 2

When an elimination reaction gives the most stable alkene as the major product,we say that the elimination follows ________________'s rule.

Accepted Answer

The answer of When an elimination reaction gives the most...

Question 3

What is the major product for the following reaction?

Accepted Answer

A)  CH3CH2(CH3)C=CHCH3 
B)  CH3CH2(CH3)CHCH=CH2 
C)  CH3CH2(CH3)CHCH(OCH2CH3)CH3 
D)  None of the above 
E)  No reaction 
A)  CH3CH2(CH3)C=CHCH3 
B)  CH3CH2(CH3)CHCH=CH2 
C)  CH3CH2(CH3)CHCH(OCH2CH3)CH3 
D)  None of the above 
E)  No reaction

Question 4

What is the major product for the following reaction?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above

Question 5

What is the major product for the following reaction?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 6

What is the major product for the following reaction sequence?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above

Question 7

What is the major product for the following reaction?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 8

What is the major product for the following reaction?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above

Question 9

Which alkene is most stable?

Accepted Answer

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

Question 10

Upon catalytic hydrogenation,a compound C6H6 absorbs four moles of hydrogen.Select a structure for C6H6.

Accepted Answer

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

Question 11

Neopentyl alcohol, (CH3)3CCH2OH,cannot be dehydrated to an alkene without rearrangement.What is the chief product of dehydration?

Accepted Answer

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

Question 12

What is the structure of a compound with formula C6H10 which has IR absorption at approximately 3300 cm-1 and which can be catalytically reduced with hydrogen to 2-methylpentane?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 13

Provide a mechanistic explanation for the formation of the observed products in the following reaction.

Accepted Answer

@#IMG-DLM& Step 1:
Acid-catalyzed dehydration of 5

Question 14

Which would be the major product of the following reaction sequence?

Accepted Answer

A)  (CH3CH2)2C=C=CHT 
B)  (CH3CH2)2C=C=CH2 
C)  (CH3CH2)2CHCCT 
D)  (CH3CH2)2CHCH=CHT 
E)  None of the above 
A)  (CH3CH2)2C=C=CHT 
B)  (CH3CH2)2C=C=CH2 
C)  (CH3CH2)2CHCCT 
D)  (CH3CH2)2CHCH=CHT 
E)  None of the above

Question 15

Which would be the major product of the following reaction sequence?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 16

What is the major product of the reaction of the following reaction?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above 
A) 
  
B) 
  
C) 
  
D) 
  
E)  None of the above

Question 17

Regarding the use of potassium tert-butoxide as a base in E2 reactions,it is incorrect to state that:

Accepted Answer

A)  this base is more effective than ethoxide ion,because it (KO-t-Bu)is the more basic of the two. 
B)  it tends to give the anti-Zaitsev,i.e. ,Hofmann,product. 
C)  it is more reactive in dimethyl sulfoxide than it is in tert-butyl alcohol. 
D)  it favors E2 reactions over competing SN2 reactions. 
E)  it will form,predominantly,the more stable alkene. 
A)  this base is more effective than ethoxide ion,because it (KO-t-Bu)is the more basic of the two. 
B)  it tends to give the anti-Zaitsev,i.e. ,Hofmann,product. 
C)  it is more reactive in dimethyl sulfoxide than it is in tert-butyl alcohol. 
D)  it favors E2 reactions over competing SN2 reactions. 
E)  it will form,predominantly,the more stable alkene.

Question 18

Which is not a satisfactory procedure for the synthesis of 3-methyl-1-butene?

Accepted Answer

A)  (CH3)2CHCHOCH3 + conc.H2SO4 
B)  (CH3)2CHC$ \equiv$CH + Li/liq.NH3 
C)  (CH3)2CHCH2CH2Br + CH3ONa/CH3OH 
D)  (CH3)2CHCHBrCH3 + (CH3)3COK/(CH3)3COH 
E)  (CH3)2CHC$ \equiv$CH + H2/Ni2B (P-2) 
A)  (CH3)2CHCHOCH3 + conc.H2SO4 
B)  (CH3)2CHC$ \equiv$CH + Li/liq.NH3 
C)  (CH3)2CHCH2CH2Br + CH3ONa/CH3OH 
D)  (CH3)2CHCHBrCH3 + (CH3)3COK/(CH3)3COH 
E)  (CH3)2CHC$ \equiv$CH + H2/Ni2B (P-2)

Question 19

Complete the following reaction sequence,providing a brief rationale for your answer.

Accepted Answer

@#IMG-DLM& Reaction with PCl₅ would afford a gemina

Exam 7: Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Rearrangements are likely to occur in which of the following reaction types?

When an elimination reaction gives the most stable alkene as the major product,we say that the elimination follows ________________'s rule.

What is the major product for the following reaction?

What is the major product for the following reaction?

What is the major product for the following reaction?

What is the major product for the following reaction sequence?

What is the major product for the following reaction?

What is the major product for the following reaction?

Which alkene is most stable?

Upon catalytic hydrogenation,a compound C6H6 absorbs four moles of hydrogen.Select a structure for C6H6.

Neopentyl alcohol, (CH3)3CCH2OH,cannot be dehydrated to an alkene without rearrangement.What is the chief product of dehydration?

What is the structure of a compound with formula C6H10 which has IR absorption at approximately 3300 cm-1 and which can be catalytically reduced with hydrogen to 2-methylpentane?

Provide a mechanistic explanation for the formation of the observed products in the following reaction.

Which would be the major product of the following reaction sequence?

Which would be the major product of the following reaction sequence?

What is the major product of the reaction of the following reaction?

Regarding the use of potassium tert-butoxide as a base in E2 reactions,it is incorrect to state that:

Which is not a satisfactory procedure for the synthesis of 3-methyl-1-butene?

Complete the following reaction sequence,providing a brief rationale for your answer.

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 Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

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

Upon catalytic hydrogenation,a compound C₆H₆ absorbs four moles of hydrogen.Select a structure for C₆H₆.

Neopentyl alcohol, (CH₃)₃CCH₂OH,cannot be dehydrated to an alkene without rearrangement.What is the chief product of dehydration?

What is the structure of a compound with formula C₆H₁₀ which has IR absorption at approximately 3300 cm^-1 and which can be catalytically reduced with hydrogen to 2-methylpentane?