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Chapter 2: Problem 79

\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3} \stackrel{\mathrm{Br}_{2} / \mathrm{hv}}{\longrightarrow}(\mathrm{A}) \stackrel{\mathrm{Mg} / \mathrm{Ether}}{\longrightarrow}(\mathrm{B}) \stackrel{\mathrm{D}_{2} \mathrm{O}}{\longrightarrow}(\mathrm{C})\) The major product \(C\) formed is (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{D}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CHD} \mathrm{CH}_{3}\) (d)

Short Answer

Expert verified
Answer: (c) \(\mathrm{CH}_{3} \mathrm{CHD} \mathrm{CH}_{3}\).

Step by step solution

01

\(Br_{2} / hv\) reaction

The first reaction involves bromination of the initial compound under light (hv). This light-catalyzed reaction is a free-radical halogenation reaction, where the main intermediate is a carbon radical. In this reaction, the halogen (Br) is added to the carbon-hydrogen (C-H) bond. The major product will be formed at the most stable carbon radical, which is the more substituted carbon (the secondary carbon in this case). So, the major product (A) will be 2-bromopropane: \(\mathrm{CH}_{3}\mathrm{CHBr}\mathrm{CH}_{3}\).
02

\(Mg / Ether\) reaction

The second reaction is the formation of a Grignard reagent using magnesium (Mg) in the presence of ether. The magnesium inserts itself between the carbon-bromine bond, forming a carbon-magnesium bond. The major product (B) after this reaction will be a Grignard reagent: \(\mathrm{CH}_{3}\mathrm{CHMgBr}\mathrm{CH}_{3}\).
03

\(D_{2}O\) reaction

The third and final reaction involves the addition of deuterium oxide (\(\mathrm{D}_{2}\mathrm{O}\)) to the Grignard reagent. The Grignard reagent will react with the deuterium from \(\mathrm{D}_{2}\mathrm{O}\), and the carbon-magnesium bond will be replaced with a carbon-deuterium bond. The major product (C) after this reaction will be: \(\mathrm{CH}_{3}\mathrm{CHD}\mathrm{CH}_{3}\). Now that we have determined the major product C, we can match it with the given options. The correct answer is: (c) \(\mathrm{CH}_{3} \mathrm{CHD} \mathrm{CH}_{3}\).

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Most popular questions from this chapter

Identify the reaction in which the equation is represented correctly (a) \(\mathrm{CF}_{3} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{HBr} \rightarrow \mathrm{CF}_{3} \mathrm{CHBr} \mathrm{CH}_{3}\)

The maximum number of optical isomers produced on monochlorination of 2 -methylbutane will be (a) 2 (b) 3 (c) 4 (d) 1

A reagent that can form a hydrocarbon with a Grignard reagent is (a) \(\mathrm{HCOOC}_{2} \mathrm{H}_{5}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COC}_{6} \mathrm{H}_{5}\)

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The silver salt of a mono acidic alkyne contains \(67 \%\) Ag. The structure of the alkyne is (a) \(\mathrm{HC} \equiv \mathrm{CH}\) (b) \(\mathrm{HC} \equiv \mathrm{C}-\mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{3}\) (d) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{CH}\)
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