Predict the major products of the following reactions, including stereochemistry. a. cyclohexene + KMnO4/H2O (cold, dilute) b. cyclohexene + peroxyacetic acid in water

Ch.8 - Reactions of Alkenes

Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook

All textbooks

Wade 9th Edition

Ch.8 - Reactions of Alkenes

Problem 34a,b

Chapter 8, Problem 34a,b

Predict the major products of the following reactions, including stereochemistry.
a. cyclohexene + KMnO₄/H₂O (cold, dilute)
b. cyclohexene + peroxyacetic acid in water

Verified step by step guidance

Step 1: For reaction (a), recognize that cyclohexene reacts with cold, dilute KMnO4 in water to undergo syn-dihydroxylation. This reaction adds two hydroxyl (-OH) groups across the double bond of the cyclohexene in a syn (same side) fashion.

Step 2: Draw the structure of cyclohexene and identify the double bond. The double bond will be the site of the reaction where the hydroxyl groups are added.

Step 3: Add two hydroxyl groups (-OH) to the carbons of the double bond in a syn fashion. This means both hydroxyl groups will be on the same face of the cyclohexane ring, resulting in a cis-1,2-diol as the product.

Step 4: For reaction (b), recognize that cyclohexene reacts with peroxyacetic acid in water to form an epoxide. This reaction is known as epoxidation, where the double bond reacts with the peroxyacid to form a three-membered cyclic ether (epoxide).

Step 5: Draw the structure of cyclohexene and identify the double bond. Replace the double bond with an epoxide ring (a three-membered oxygen-containing ring). Ensure to consider stereochemistry, as the epoxide will form on one face of the cyclohexane ring.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Video duration:

11m

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Oxidation Reactions

Oxidation reactions involve the addition of oxygen or the removal of hydrogen from a molecule. In the context of cyclohexene reacting with KMnO4, this reaction leads to the formation of diols through syn-dihydroxylation, where hydroxyl groups are added to adjacent carbon atoms in a cyclic manner, preserving stereochemistry.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving alkenes like cyclohexene, the stereochemical outcome is crucial, especially in syn-addition reactions, where the orientation of substituents on the resulting product can lead to different isomers.

Peracid Reactions

Peracid reactions involve the use of peracids, such as peroxyacetic acid, to oxidize alkenes. This reaction typically results in the formation of epoxides or diols, depending on the conditions. The mechanism involves the electrophilic attack of the peracid on the double bond, leading to the formation of a cyclic ether (epoxide) that can further react with water to yield diols.

Recommended video:

Guided course

05:09

Heck Reaction

Related Practice

Textbook Question

Predict the major products of the following reactions, including stereochemistry.

e. trans-pent-2-ene + OsO₄/H₂O₂

1250

views

Textbook Question

Predict the major products of the following reactions, including stereochemistry.

c. cis-pent-2-ene + OsO₄/H₂O₂

d. cis-pent-2-ene + peroxyacetic acid in water

1922

views

Textbook Question

When 1,2-epoxycyclohexane (cyclohexene oxide) is treated with anhydrous HCl in methanol, the principal product is trans-2-methoxycyclohexanol. Propose a mechanism to account for the formation of this product.

Predict the major products of the following reactions.

b. trans-hex-3-ene + peroxyacetic acid (CH₃CO₃H) in water

c. 1-methylcyclohexene + MMPP in ethanol

2229

views

Textbook Question

Predict the major products of the following reactions.

d. trans-cyclodecene + peroxyacetic acid in acidic water