Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

Question: Arrange the carbocations below, in order of increasing stability:

b.

Question: Arrange the carbocations below, in order of increasing stability.

c.

Question: Order each of the following sets of compounds with respect to reactivity:

Question: Order each of the following sets of compounds with respect to reactivity:

b. (CH₃)₃ CCI (CH₃)₃  CBr (CH₃)₃  COH

Question: Order each of the following sets of compounds with respect to reactivity:

Question: Order each of the following sets of compounds with respect to reactivity:

a.

Question: Order each of the following sets of compounds with respect to reactivity:

b.

Question: Order each of the following sets of compounds with respect to reactivity:

c.   CH₃ CH₂ CH₂ OCH₃   CH₃ CH₂ CH₂OTs   CH₃ CH₂ CH₂ Br

Reaction of the following S to sylate with cyanide ion yields a nitrile product that also has S stereochemistry. Explain.

Ethers can often be prepared by SN2 reaction of alkoxide ions,${\mathbf{RO}}^{-}$ , with alkyl halides. Suppose you wanted to prepare cyclohexyl methyl ether. Which of the two possible routes shown below would you choose? Explain.

Treatment of 1-bromo-2-deuterio-2-phenylethane with strong base leads to a mixture of deuterated and nondeuterated phenylethylenes in an approximately 7;1 ratio. Explain