2-Ethoxy-2,3-dimethylbutane reacts with concentrated aqueous HI to form two initial organic products (A and B). Further reaction with HI produces organic product C from product B. Draw the structures of these three products. (Picture attached)

Question

Question

2-Ethoxy-2,3-dimethylbutane reacts with concentrated aqueous HI to form two initial organic products (A and B). Further reaction with HI produces organic product C from product B. Draw the structures of these three products. (Picture attached)

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Answer 1

Answer #1

When one group is methyl and the other alkyl group is a tertiary group, the halide formed is a tertiary group. Thus, 2-ethoxy

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Answer 2

Answer #2

Concepts and reason

The concept used to solve this question is cleavage of ether takes place with strong acid, HI and forms an alcohol, alkyl iodide, which is further reacted with HI to form second alkyl iodide.

Fundamentals

The mechanism of ether cleavage takes place via ${{\rm{S}}_{\rm{N}}}{\rm{1}}$ or ${{\rm{S}}_{\rm{N}}}{\rm{2}}$ .

With the methyl or primary alkyl groups that are bonded to ether oxygen, the cleavage of C-O bond takes place via ${{\rm{S}}_{\rm{N}}}{\rm{2}}$ mechanism. Similarly, with the secondary or tertiary alkyl groups that are bonded to ether oxygen, the cleavage of C-O bond takes place via ${{\rm{S}}_{\rm{N}}}{\rm{1}}$ mechanism.

The reaction is as follows:

.—CHz-CH3
conc.HI (aq)
19cmçu—chs
CH3 CH3
2-ethoxy-2,3-dimethylbutane
H3C4
C H-CH3
+ HO-CH2-CH3
ethanol
CH3 CH3
2-iodo-2,3-di

The reaction is as follows:

conc.HI (aq)
HO-CH2-CH3 S-CH2-CH3
ethanol
iodoethane

Ans:

The structures of three products are as follows:

HC
— сн— Сн,
CH3
CH3 CH3
HO-CH2-CH3
в
CH2-CH3
с

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Answer 3

2-Ethoxy-2,3-dimethylbutane reacts with concentrated aqueous HI to form two initial organic products (A and B). Further reaction with HI produces organic product C from product B. Draw the structures of these three products. (Picture attached)

Homework Answers

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2-Ethoxy-2,3-dimethylbutane reacts with concentrated aqueous HI to form two initial organic products (A and B). Further reaction with HI produces organic product C from product B. Draw the structures of these three products. (Picture attached)

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