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Exam 8: Reactions of Alkenes

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Question 1

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Which of the following additions to alkenes occur(s) specifically in an syn fashion?

A) dihydroxylation using OsO₄, H₂O₂
B) addition of H₂
C) hydroboration
D) addition of HCl
E) A, B, and C

F) B) and C)
G) A) and D)

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E

Question 2

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Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

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Question 3

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Predict the product of the following reaction. Include any relevant stereochemistry.

Humulene is a monocyclic terpene constituent of carnations. When 0.25 mol of humulene is hydrogenated in the presence of platinum catalyst, 0.75 mol of H₂ reacts with the humulene to produce a monocyclic hydrocarbon of formula C₁₅H₃₀. What is the molecular formula of humulene?

Provide the major organic product of the reaction below.

β-Ocimene is a natural product with a pleasant odor. Based on the information below, deduce the structure of β-ocimene.

HBr can be added to an alkene in the presence of peroxides (ROOR) . What function does the peroxide serve in this reaction?

Complete the following reaction by filling in the necessary reagents.

What is the major product of the following reaction?

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

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

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

When propylene reacts with hydrogen bromide in the presence of a peroxide initiator, which of the following structures are formed during the mechanism?

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. (Z)-3-hexene →

Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Predict the major product of the following reaction.

Give the structure of the alkene which would yield the following products upon ozonolysis-reduction. CH₃COCH₃ + CH₃CH₂CHO

Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene.

Name the major alcohol product which results when 3,3-dimethylbut-1-ene is treated with dilute acid.