Predict the major, organic product of the following reaction.

In addition to radicals, anions, and cations, a fourth class of reactive intermediates is carbenes. A neutral species, the simplest carbene has a molecular formula of CH₂.

(f) Cyclopropanation of (E)- and (Z)-3-methylhex-3-ene gives two different products. Rationalize this outcome.

Suggest a mechanism for the reaction shown in Figure 16.30 using IZnCH₂I as the cyclopropanating reagent.

Two chemists at Dupont found that ICH₂ZnI is better than diazomethane at converting a C=C bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the Simmons–Smith reaction in their honor.

When dichloromethane is treated with strong NaOH, an intermediate is generated that reacts like a carbene. Draw the structure of this reactive intermediate, and propose a mechanism for its formation.

Dichlorocarbene can also be generated by heating sodium trichloroacetate. Propose a mechanism for the reaction.

Show how you would accomplish each of the following synthetic conversions.

(b)