Chapter 17: Problem 376

Predict the product(s) of the reaction of ethylene oxide with (a) \(\mathrm{H}_{3} \propto\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{MgBr}\), then \(\mathrm{H}_{3} \alpha\)

Short Answer

Expert verified

In the first reaction, the product formed is an ethanolamine with the structure \(\ce{H2N-CH2-CH2OH}\) after the attack of the nucleophilic \(\mathrm{H}_{3} \propto\) on the electrophilic carbon in ethylene oxide. In the second reaction, the Grignard reagent \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{MgBr}\) attacks the electrophilic carbon, followed by the addition of \(\mathrm{H}_{3} \alpha\) to produce 1,2-propanediol with the structure \(\ce{CH3-CH2-CH2-O-CH2-CH2OH}\).

Step by step solution

1. Reaction of ethylene oxide with \(\mathrm{H}_{3} \propto\)

Ethylene oxide is an epoxide, so its three-membered ring is strained. When ethylene oxide reacts with \(\mathrm{H}_{3} \propto\), the nucleophilic species in the reaction is \(\mathrm{H}_{3} \propto\), which has a basic nitrogen atom. This nitrogen will attack the electrophilic carbon of the epoxide, opening the ring and forming a new bond between the nitrogen and the carbon. The resulting product is an ethanolamine, with the structure \(\ce{H2N-CH2-CH2OH}\).

2. Reaction of ethylene oxide with \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{MgBr}\), then \(\mathrm{H}_{3} \alpha\)

In this case, the ethylene oxide reacts with a Grignard reagent. As the Grignard reagent is a strong nucleophile, it will also attack the electrophilic carbon of the epoxide and open the strained ring. The carbon attached to the magnesium will form a new bond with the carbon of the epoxide. After this attack, the structure will be \(\ce{CH3-CH2-CH2-O-CH2-CH2-MgBr}\). Subsequently, this intermediate species will be reacted with \(\mathrm{H}_{3} \alpha\), providing a proton for the oxygen in the intermediate species. This proton will bond with the oxygen, converting the alkoxide to an alcohol group, and the final product will be \(\ce{CH3-CH2-CH2-O-CH2-CH2OH}\). This compound is also known as 1,2-propanediol.

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Predict the product(s) of the reaction of ethylene oxide with (a) \(\mathrm{H}_{3} \propto\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{MgBr}\), then \(\mathrm{H}_{3} \alpha\)

Short Answer

Step by step solution

1. Reaction of ethylene oxide with \(\mathrm{H}_{3} \propto\)

2. Reaction of ethylene oxide with \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{MgBr}\), then \(\mathrm{H}_{3} \alpha\)

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