91Ó°ÊÓ

Radical chlorination of alkanes is not generally useful because mixtures of products often result when more than one kind of \(\mathrm{C}-\mathrm{H}\) bond is present in the substrate. Draw and name all monochloro substitution products \(\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{Cl}\) you might obtain by reaction of 2 -methylpentane with \(\mathrm{Cl}_{2}\).

What product would you expect from acid-catalyzed reaction of cyclohexene with \(\mathrm{H}_{2} \mathrm{O}\) ?

Acid-catalyzed reaction of \(\mathrm{H}_{2} \mathrm{O}\) with 2-methylpropene yields 2 -methylpropan-2-ol. What is the structure of the carbocation formed during the reaction? Show the mechanism of the reaction.

Sketch an energy diagram for a two-step reaction with an endergonic first step and an exergonic second step. Label the parts of the diagram corresponding to reactant, product, and intermediate.

A The reaction of hydroxide ion with chloromethane to yield methanol and chloride ion is an example of a general reaction type called a nucleophilic substitution reaction: $$ \mathrm{HO}^{-}+\mathrm{CH}_{3} \mathrm{Cl} \rightleftarrows \mathrm{CH}_{3} \mathrm{OH}+\mathrm{Cl}^{-} $$ The value of \(\Delta H^{\circ}\) for the reaction is \(-75 \mathrm{~kJ} / \mathrm{mol}\), and the value of \(\Delta S^{\circ}\) is \(+54 \mathrm{~J} /(\mathrm{K} \cdot \mathrm{mol})\). What is the value of \(\Delta G^{\circ}\) (in \(\mathrm{kJ} / \mathrm{mol}\) ) at \(298 \mathrm{~K} ?\) Is the reac- tion exothermic or endothermic? Is it exergonic or endergonic?

ammonia reacts with acetyl chloride \(\left(\mathrm{CH}_{3} \mathrm{COCl}\right)\) to give acetamide \(\left(\mathrm{CH}_{3} \mathrm{CONH}_{2}\right)\). Identify the bonds broken and formed in each step of the reaction, and draw curved arrows to represent the flow of electrons in each step.

Reaction of 2-methylpropene with \(\mathrm{H}_{3} \mathrm{O}^{+}\) might, in principle, lead to a mixture of two alcohol addition products. Draw their structures.