Exam 8: Alkenes and Alkynes Ii: Addition Reactions

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Give a mechanistic explanation for the formation of the following product in significant yield.What other product(s)might also be obtained? Explain clearly.

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Question 1

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The regioselective addition of a proton first generates a secondary carbocation,which can undergo rearrangement to a more stable 3^o carbocation by two alternate pathways.One pathway results in ring expansion to a more stable 5-membered ring.This pathway is thus more likely,which would then lead to the observed product.The other pathway is less likely,since ring strain is not relieved;however,this could lead to a minor product,as shown above.

What is the major product for the following reaction?

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Question 2

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What is the major product of the following reaction sequence?

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Question 3

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Which reaction would yield a meso compound?

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Question 4

The reaction of Br₂/CCl₄ to cyclohexene would produce the compound(s)represented by structure(s):

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Question 5

A reagent or test that could be used to distinguish between 1-pentene and 1-pentyne would be:

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Question 6

What is the major product of the following reaction sequence?

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Question 7

What is the major product for the following reaction?

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Question 8

Markovnikov addition of HI to 2-methyl-2-butene involves:

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Question 9

Which reaction is regioselective?

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Question 10

Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?

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Question 11

Deduce the structure of an unknown compound A,C₈H₁₄,from the following data.Briefly,but clearly explain your rationale.A decolorizes Br₂/CCl₄,and upon reaction with excess H₂/Ni,affords 1-ethyl-2-methylcyclopentane.When A is subjected to ozonolysis,the following product is obtained.

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Question 12

Which of the following could be used to distinguish between 1-octyne and 3-octyne?

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Question 13

Which reagent or test could be used to distinguish between 2-methyl-2-pentene and 2-methylpentane?

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Question 14

Compound X has the molecular formula C₆H₁₀.X decolorizes bromine in carbon tetrachloride.X also shows IR absorption at about 3300 cm^-1.When treated with excess hydrogen and a nickel catalyst,X yields 2-methylpentane.The most likely structure for X is:

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Question 15

What is the major product of the following reaction sequence?

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Question 16

What is the major product for the following reaction?

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Question 17

What is the major product for the following reaction?

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Question 18

Addition of hydrogen chloride to the following molecule would produce:

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Question 19

What is the major product of the following reaction sequence?

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Question 20

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Exam 8: Alkenes and Alkynes Ii: Addition Reactions

Give a mechanistic explanation for the formation of the following product in significant yield.What other product(s)might also be obtained? Explain clearly.

What is the major product for the following reaction?

What is the major product of the following reaction sequence?

Which reaction would yield a meso compound?

The reaction of Br2/CCl4 to cyclohexene would produce the compound(s)represented by structure(s):

A reagent or test that could be used to distinguish between 1-pentene and 1-pentyne would be:

What is the major product of the following reaction sequence?

What is the major product for the following reaction?

Markovnikov addition of HI to 2-methyl-2-butene involves:

Which reaction is regioselective?

Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?

Deduce the structure of an unknown compound A,C8H14,from the following data.Briefly,but clearly explain your rationale.A decolorizes Br2/CCl4,and upon reaction with excess H2/Ni,affords 1-ethyl-2-methylcyclopentane.When A is subjected to ozonolysis,the following product is obtained.

Which of the following could be used to distinguish between 1-octyne and 3-octyne?

Which reagent or test could be used to distinguish between 2-methyl-2-pentene and 2-methylpentane?

Compound X has the molecular formula C6H10.X decolorizes bromine in carbon tetrachloride.X also shows IR absorption at about 3300 cm-1.When treated with excess hydrogen and a nickel catalyst,X yields 2-methylpentane.The most likely structure for X is:

What is the major product of the following reaction sequence?

What is the major product for the following reaction?

What is the major product for the following reaction?

Addition of hydrogen chloride to the following molecule would produce:

What is the major product of the following reaction sequence?

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

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

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The reaction of Br₂/CCl₄ to cyclohexene would produce the compound(s)represented by structure(s):

Deduce the structure of an unknown compound A,C₈H₁₄,from the following data.Briefly,but clearly explain your rationale.A decolorizes Br₂/CCl₄,and upon reaction with excess H₂/Ni,affords 1-ethyl-2-methylcyclopentane.When A is subjected to ozonolysis,the following product is obtained.

Compound X has the molecular formula C₆H₁₀.X decolorizes bromine in carbon tetrachloride.X also shows IR absorption at about 3300 cm^-1.When treated with excess hydrogen and a nickel catalyst,X yields 2-methylpentane.The most likely structure for X is: