In one industrial synthesis of ethanol, ethene first...

Name: Problem 5, Chapter 8: Organic Chemistry
Uploaded: 2020-07-13T01:31:00-08:00
Duration: 3 min 3 s
Channel: Kaitlynn Wade
Description: In one industrial synthesis of ethanol, ethene first undergoes an addition reaction with sulfuric acid, and this product undergoes hydrolysis to ethanol. Write a mechanism for the addition of sulfuric acid to ethene.

In one industrial synthesis of ethanol, ethene first undergoes an addition reaction with sulfuric acid, and this product undergoes hydrolysis to ethanol. Write a mechanism for the addition of sulfuric acid to ethene.

Key Concepts

Nucleophilic Attack

After the carbocation intermediate is formed, a nucleophile, which bears an electron pair, attacks the electron-deficient carbon center. This nucleophilic attack completes the electrophilic addition, resulting in the formation of a new covalent bond and leading to the final product of the reaction.

Protonation Step

The protonation step involves the initial addition of a proton to the alkene’s double bond. This step is driven by the electrophilic nature of the proton and results in the formation of a carbocation intermediate. The orientation of the proton addition is influenced by the stability of the possible carbocations, following Markovnikov’s rule.

Acid Catalysis

Acid catalysis plays an essential role in facilitating the electrophilic addition process. Strong acids, such as sulfuric acid, provide the proton that initiates carbocation formation and are regenerated after the nucleophilic attack, making them effective catalysts that promote the reaction without being consumed in the process.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile, often derived from a proton donor like an acid, adds to a carbon-carbon double bond. This addition converts the unsaturated alkene into a saturated product, typically through the formation of an intermediate that allows the reaction to proceed with added regiochemical control.

Carbocation Intermediate

The formation of a carbocation intermediate is a key step in many electrophilic addition reactions. When a proton from an acid adds to an alkene, it creates a positively charged carbocation. This intermediate is highly reactive and determines the regiochemistry of the subsequent nucleophilic attack, making its stability crucial to the success of the reaction.

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