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Chapter 6: Problem 34

Treating 4-penten- \(1-\mathrm{ol}\) with bromine in water forms a cyclic bromoether.

Short Answer

Expert verified
Answer: The product formed is a cyclic bromoether with the structure CH3-CH2-CH-O-CHBr-CH2OH.

Step by step solution

01

Formation of the cyclic bromonium ion

Begin by writing the structure of 4-penten-1-ol and bromine (Br2). In this reaction, the electron-rich alkene double bond of 4-penten-1-ol will undergo electrophilic addition with bromine. The bromine atom will attack the alkene, forming a cyclic bromonium ion and a bromide ion. 4-penten-1-ol: CH3-CH2-CH=CH-CH2OH Bromine: Br2 Cyclic bromonium ion: CH3-CH2-CH(Br)-CH-CH2OH Bromide ion: Br-
02

Intramolecular nucleophilic substitution

Now, the hydroxyl group (-OH) from the alcohol part of the molecule will act as a nucleophile, attacking the carbon atom bearing the bromine in the cyclic bromonium ion. This results in the formation of a cyclic ether and release of a bromide ion. Cyclic ether: CH3-CH2-CH-O-CH-CH2OH
03

Deprotonation of the cyclic ether

The formation of the cyclic ether can be further stabilized by deprotonation of the adjacent hydrogen atom, using water as a base. This allows the molecule to reach a more energetically stable state, as the electrons on the oxygen can participate in resonance with the adjacent carbon double bond. The deprotonation yields a cyclic bromoether as the final product. Cyclic bromoether: CH3-CH2-CH-O-CHBr-CH2OH In summary, treating 4-penten-1-ol with bromine in water forms a cyclic bromoether through an electrophilic addition followed by an intramolecular nucleophilic substitution.

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Most popular questions from this chapter

Account for the fact that treating propenoic acid (acrylic acid) with \(\mathrm{HCl}\) gives only S-chloropropanoic acid.

Account for the fact that addition of HCl to 1-bromopropene gives exclusively 1-bromo1-chloropropane. $$ \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHBr}+\mathrm{HCl} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHBrCl} $$ 1-Bromopropene 1-Bromo-1-chloropropane

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