Question

Which of the following alkyl iodides cannot be produced by the reaction of HI with an appropriate ether?

(a) CH₃I
(b) C₂H₅I
(c) (CH₃)₃CI
(d) (C₂H₅)₃CI

Answer 1

Among the given options, (C₂H₅)₃CI cannot be produced by the reaction of HI with an appropriate ether because the corresponding ether, triethyl ether, is not stable or common.

Step-by-step explanation:

The reaction of hydroiodic acid (HI) with ethers typically forms alkyl iodides, but the question asks which of the alkyl iodides cannot be produced by the reaction of HI with an appropriate ether. Of the options given, the one that cannot be produced is (C₂H₅)₃CI. This is because the corresponding ether that would yield (C₂H₅)₃CI upon reaction with HI would be triethyl ether (an ether with three ethyl groups attached to a central carbon), which is not stable or commonly encountered due to steric hindrance.

Answer 2

The alkyl iodide that cannot be produced by the reaction of HI with an appropriate ether is (C₂H₅)₃CI due to the presence of a quaternary carbon atom, which is resistant to cleavage.

Step-by-step explanation:

The question asks which of the following alkyl iodides cannot be produced by the reaction of hydroiodic acid (HI) with an appropriate ether: (a) CH₃I, (b) C₂H₅I, (c) (CH₃)₃CI, or (d) (C₂H₅)₃CI. When ethers react with hydroiodic acid, the reaction generally results in the cleavage of the ether to form an alkyl iodide and an alcohol. However, this reaction typically works well with primary and secondary alkyl groups, whereas tertiary alkyl groups do not generally undergo such cleavage due to steric hindrance and the difficulty of forming a carbocation intermediate.

The correct answer to the student's question is (d) (C₂H₅)₃CI because it involves a quaternary carbon atom which does not easily undergo the cleavage reaction necessary to produce the corresponding alkyl iodide in this situation.