91Ó°ÊÓ

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane:

(b) $C{H}_{3}C{O_2}^{-}$

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane:

(c)$C{H}_3{S}^{-}$

Question: (R)-2-Bromooctane undergoes racemization to give ($Â\pm$)-2-bromooctane when treated with NaBr in dimethyl sulfoxide. Explain.

Question: Propose structures for compounds that fit the following descriptions:

(a) An alkyl halide that gives a mixture of three alkenes on E₂ reaction

Question: Propose structures for compounds that fit the following descriptions:

(b) An organohalide that will not undergo nucleophilic substitution

Question: Propose structures for compounds that fit the following descriptions:

(c) An alkyl halide that gives the non-Zaitsev product onreaction

Question: Propose structures for compounds that fit the following descriptions:

(d) An alcohol that reacts rapidly with HCl at 0 °C

What product would you expect from ${\mathbf{S}}_{\mathbf{N}}\mathbf{2}$reaction of 1-bromobutane with each of the following?

(a)NaI (b) KOH (c)$\mathbf{H}\mathbf{—}\mathbf{C}≡\mathbf{C}\mathbf{—}\mathbf{Li}$(d)${\mathbf{NH}}_{\mathbf{3}}$

Question: 1-Chloro-1,2-diphenylethane can undergo E2 elimination to give either cis- or trans-1,2-diphenylethylene (stilbene). Draw Newman projections of the reactive conformations leading to both possible products, and suggest a reason why the trans alkene is the major product.

Question: Predict the major alkene product of the following E1 reaction: