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Exam 8: Haloalkanes, Halogenation, and Radical Reactions

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Question 1

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What is the structure of the key intermediate in the following reaction?

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Question 2

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Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point) ?

A) 2-fluoropropane > 2-chloropropane > 2-bromopropane > 2-iodopropane
B) 2-chloropropane > 2-iodopropane > 2-fluoropropane > 2-bromopropane
C) 2-iodopropane > 2-chloropropane > 2-fluoropropane > 2-bromopropane
D) 2-iodopropane > 2-bromopropane > 2-chloropropane > 2-fluoropropane

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Question 3

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What is the major organic product obtained from the following reaction?

Consider the reaction below to answer the following question(s). $\begin{array}{ccccc}\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}&\underset{h v}{\stackrel{\text { NBS }}{\rightarrow}} &\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCHCH}_{2} \mathrm{CH}_{3}&+&\mathrm{CH}_{3} \mathrm{CHCH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}\\&&|&&|\\&&\mathrm{Br}&&\mathrm{Br}\\A&&B&&C\end{array}$ -The name of one of the minor products of this reaction is____________________.

Which of the following statements is not true?

Which of the following alkanes does not undergo monobromination to form a single bromoalkane as the major product?

What is the major organic product obtained from the following reaction?

What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction?

What is the reactive intermediate in the autooxidation of cyclohexene?

Provide neatly drawn resonance structures of the key intermediate in the following reaction.

What are the major organic products obtained from the following reaction?

What is the correct order of stability of the following radicals (more stable > less stable) ?

What type of orbital contains the unpaired electron of the tert-butyl radical?

What is the major organic product obtained from the following reaction?

The products of the addition of HBr to an alkene in the presence of peroxides is accounted for by a polar reaction mechanism.

What is the major organic product obtained from the following reaction?

During bromination using NBS, the addition product is not observed because the rate of addition is _______than the rate of the chain propagation steps.

Which of the following bonds has the lowest bond dissociation enthalpy?

What is the major product formed upon radical bromination of (S) -3-methylhexane?

What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides?