Exam 6: Alkyl Halides; Nucleophilic Substitution

A sample of 1-chloro-1-phenylethane with an [α]²⁵_D of -94.8° is reacted with NH₃ in methanol/water solvent. The major substitution product of the reaction is 1-phenyl-1-ethylamine with an [α]²⁵_D of -8.6°. Given that optically pure (R) 1-chloro-1-phenylethane has a specific rotation of -109.0° and that optically pure (R) 1-phenyl-1-ethylamine has a specific rotation of +39.3°, which of the following statements best describes this reaction?

Provide a series of synthetic steps by which (CH₃)₂C CH₂ could be prepared from 2-methylpropane.

Predict the structure of the expected product for the following reaction.

Which of the following alkyl bromides undergoes solvolysis in aqueous methanol most rapidly?

When 1-iodo-1-methylcyclohexane is treated with NaOCH₂CH₃, the more highly substituted alkene product predominates. When KOC(CH₃)₃ is used instead, the less highly substituted alkene product predominates. Offer an explanation.

Provide a structure for the major substitution and major elimination product resulting from the reaction below.

What is the IUPAC name of the compound shown below?

Draw the structure of cis-1,3-dichlorocyclopentane.

Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

Do all primary iodides react with N₃^- at the same rate via the S_N2 mechanism? Explain.

When 2,2-dimethylbutane is subjected to free-radical chlorination, ________ distinct monochlorinated products are possible and ________ of these contain asymmetric carbon atoms.

S_N2 reactions take place with ________ of stereochemistry at the center undergoing substitution.

Which of the following is a tertiary halide?

How many distinct alkene products results when 1-bromo-1-ethylcyclopentane is treated with NaOCH₃?

Provide the major organic product of the reaction below.

The flame retardant below has been found to be an androgen agonist and may have a contribution to an increasing rate of occurrence of prostate cancer (J. Med. Chem. 2006, 7366). What is the correct term that describes the relative position of the bromides in this structure?

Consider the reaction of (CH₃)₃CO^- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

When trans-1-iodo-4-methylcyclohexane is heated in methanol, the product mixture is primarily ________.

Draw a chair conformation of the starting substituted cyclohexane molecule with the bromine in the axial position. Using this model, predict the major elimination product of this reaction.