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What product would you expect from the reaction of 1-phenyl-2-butene with NBS? Explain.

1-phenyl 2-butene

Rank the compounds in each of the following series in order of increasing oxidation level:

Which of the following compounds have the same oxidation level, and which have different levels?

Question: (S)-3-Methylhexane undergoes radical bromination to yield optically inactive 3-bromo-3-methylhexane as the major product. Is the product chiral? What conclusions can you draw about the radical intermediate?

Draw and name all monochloro products you would expect to obtain from radical chlorination of 2-methylpentane. Which, if any, are chiral?

How would you carry out the following syntheses?

Question: The syntheses shown here are unlikely to occur as written. What is

wrong with each?

Reaction 1

Reaction 2

Question: Addition of HBr to a double bond with an ethersubstituentoccurs regiospecifically to give a product in which theandare bonded to the same carbon. Draw the two possible carbocation intermediates in this electrophilic addition reaction, and explain usingresonance why the observed product is formed.

Identify the reagents a–c in the following scheme:

Tertiary alkyl halides,${\mathbf{R}}_3\mathbf{CX}$, undergo spontaneous dissociation to yield a carbocation,${\mathbf{R}}_3{\mathbf{C}}^{+}$, plus halide ion. Which do you think reacts faster,${{\text{(CH}}_3\text{)}}_3{\text{CBrorH}}_2{\text{C=CHC(CH}}_3{\text{)}}_2\text{Br}$? Explain.