Question

The nucleophile in the Wittig reaction is a phosphorous-stabilized carbanion called an ylide. The ylides are synthesized by employing a strong base to remove an acidic proton and a halogen from a alkyl triphenylphosphonium halide salt. The alkyl triphenylphosphonium halide salts are made via an SN2 reaction between an appropriate alkyl halide substrate and triphenylphosphine. So we could consider these SN2 reactions as the "first step" in a multi-step Wittig synthesis. Could bromobenzene be a starting material in one of these first steps?

yes or no

Referring to the previous question, could t-butyl bromide (aka 2-bromo-2-methylpropane) be used in the first step of a Wittig synthesis?

ye or no

Referring to the first question again, could methyl bromide (bromomethane or bromoform) be used as a starting material?

yes or no

Referring to the first question again, could 1-bromo-2,2-dimethylpropane (aka neopentyl bromide) be used as a starting material?

yes or no?

You want to prepare the compound trans-1-phenylprop-1-ene by a Wittig synthesis. (Hint: Draw the structure of this compound so you know what we are talking about.) One way to do this is to react benzaldehyde with the ylide of ethyl bromide. Is there another way to make this compound by the Wittig route using different starting materials?

yes or no?

Answer 1