Leaving Group Conversions - Using HX Practice Problems

Provide the product of the reaction:

One method to convert an alcohol into an alkyl iodide is by using triphenylphosphine and iodine. Provide a mechanism for the reaction below. (Hint: triphenylphosphine first acts as a nucleophile.)

Draw a suitable mechanism for the substitution reaction shown below.

Why does the heated reaction of 3-methyl-2-pentanol with concentrated HI produce a rearranged product while the reaction of 4-Methyl-1-pentanol under the same conditions does not?

Provide a suitable reaction to carry out the following synthesis.

Formation of 2-cyclohexylethan-1-ol from (2-bromoethyl)cyclohexane using an S_N2 reaction.

Provide a suitable reaction to carry out the following synthesis.

(a) Formation of 3,6-dimethyloctane from 1-bromo-2-methylbutane

Write a mechanism for the reaction of 2-methylbutan-2-ol with concentrated HCl goes by an S_N1 reaction.

Propose a mechanism for the formation of rearranged product, when 2,2-dimethylheptan-1-ol reacts with concentrated HBr to give 3-bromo-3-methyloctane.

Provide a chemical test to distinguish the members of each of the following pairs of compounds.
a. (E)-hept-3-en-2-ol and heptan-1-ol
b. heptan-2-one and 2-methylheptan-2-ol

Provide the explanation for the products observed in the following reaction.