Skip to main content
Ch. 7 - Structure and Synthesis of Alkenes; Elimination
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 7, Problema 54c

Write a balanced equation for each reaction, showing the major product you expect.
(c) Chemical structure showing two hydroxyl groups on a hexagonal ring, with sulfuric acid and heat indicated for dehydration reaction.

Guida verificata passo dopo passo
1
Step 1: Analyze the reactant structure. The molecule is a cyclohexane ring with two hydroxyl (-OH) groups attached to adjacent carbons. This is a diol (vicinal diol).
Step 2: Recognize the reaction conditions. The presence of concentrated sulfuric acid (H₂SO₄) and heat suggests a dehydration reaction, where water molecules are eliminated.
Step 3: Understand the mechanism. Under acidic conditions, one hydroxyl group is protonated, forming a good leaving group (water). The adjacent hydroxyl group can then lose a proton, leading to the formation of a carbocation intermediate.
Step 4: Predict the major product. The carbocation intermediate undergoes rearrangement or stabilization, followed by elimination of a proton from a neighboring carbon to form a double bond. This results in the formation of an alkene. In this case, the major product is likely cyclohexene.
Step 5: Write the balanced equation. The reaction eliminates two molecules of water (H₂O) from the diol, forming cyclohexene as the major product. The balanced equation is: C6H12O2→C6H10+2H2O.

Risposta video verificata per un problema simile:

Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Durata del video:
3m

Concetti chiave

Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.

Dehydration Reaction

A dehydration reaction involves the removal of water (H2O) from a molecule, often resulting in the formation of a double bond or a ring structure. In organic chemistry, this process is commonly facilitated by heat and an acid catalyst, such as sulfuric acid, which helps to protonate the hydroxyl groups, making them better leaving groups.
Video consigliato:
01:23
General Reaction of Dehydration with POCl3

Acid-Catalyzed Reactions

Acid-catalyzed reactions utilize an acid to increase the rate of a chemical reaction. In the context of dehydration, sulfuric acid donates protons to the hydroxyl groups, enhancing their ability to leave as water. This mechanism is crucial for driving the reaction forward and achieving the desired product.
Video consigliato:
03:09
Acid Catalyzed

Major Product Formation

In organic reactions, the major product is the most stable or predominant product formed under the given reaction conditions. Factors such as sterics, electronics, and the stability of intermediates influence which product is favored. Understanding these factors is essential for predicting the outcome of the dehydration reaction shown in the question.
Video consigliato:
04:28
Predict the MAJOR product.