Exam 6: Alkyl Halides; Nucleophilic Substitution

Dehydration of 1-butanol with concentrated sulfuric acid at 140^∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?

Which of the following alkyl chlorides will undergo S_N2 reaction most readily?

Which of the following alkyl halides is most likely to undergo rearrangement in an S_N1 reaction?

Provide the structure of the major organic product which results in the following reaction.

When t-butyl chloride undergoes solvolysis in a solvent mixture composed of 70% water/30% acetone, the reaction rate is slower than when the same compound is solvolyzed in 80% water/20% acetone. Explain.

Among the following alkyl halides, choose the one with the lowest boiling point.

List the following bromides in order of their increasing reactivity as substrates in S_N1 reactions: 2-chlorobutane, 2-iodobutane, and 1-iodobutane.

Which is more nucleophilic, t-butoxide or ethoxide? Explain.

One product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. From which mechanistic pathway does this ether arise?

In which of the following mechanisms (S_N1, S_N2, E1, E2) are alkenes the major reaction products?

Provide the structure of the major organic product in the following reaction.

S_N1 reactions usually proceed with ________.

Provide a step-by-step mechanism for the reaction below. Include all intermediates, formal charges and correct arrow pushing of electrons.

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

List the following alkyl halides in order of their increasing reactivity as substrates in S_N2 reactions: 2-chlorobutane, 2-iodobutane, and 1-iodobutane.

Which of the following alkyl chlorides is least likely to undergo rearrangement during a solvolysis reaction?

Provide an acceptable name for CH₃CH₂CH₂C(CH₃)₂I.

Consider the substitution reaction shown below. By what mechanism will the reaction proceed?

Which of the following factors is favorable for nucleophilicity but not basicity?

Which of the following statements describe a favorable attribute of a leaving group? (More than one answer is possible.)