Exam 6: Alkyl Halides; Nucleophilic Substitution

List the following bromides in order of their increasing reactivity as substrates in S_N1 reactions: 1-iodo-1-ethylcyclopentane, chlorocyclopentane, and iodocyclopentane.

Which of the following compounds is the most nucleophilic?

Rank the species below in order of increasing nucleophilicity in hydroxylic solvents: CH₃CO₂^-, CH₃S^-, HO^-, H₂O.

Provide the major organic product of the reaction below.

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

Which of the following alkyl halides reacts most rapidly via an S_N1 solvolysis reaction in hot methanol?

Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis or the trans, undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.

When (cis)-1-bromo-2 methylcyclohexane is treated with methanol and heat, four different products are formed - two by substitution and two by elimination. Which of the following conditions would change the outcome of this reaction by promoting the production of 3-methylhexene as the major product?

Predict the two most likely mechanisms for the reaction of 2-iodohexane with potassium hydroxide.

The term CFC is an abbreviation for ________.

Provide the major organic product of the S_N2 reaction below.

Which of the following alkyl halides has the smallest molecular dipole moment?

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

Provide the major organic product of the reaction below.

Which of the following species is the least nucleophilic?

Predict the most likely mechanism for the reaction shown below.

Provide two circumstances under which solvolysis of a chiral alkyl halide would not result in the generation of a mixture of enantiomeric products.

Which of the following is a primary alkyl halide?

When 3-iodo-3-ethylpentane is heated in methanol, the major organic product is an ________ that is generated through an ________ mechanism.