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Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Related Experiment Video

Updated: May 19, 2026

Microwave-Assisted Extraction of Phenolic Compounds and Antioxidants for Cosmetic Applications Using Polyol-Based Technology

Microwave-Assisted Extraction of Phenolic Compounds and Antioxidants for Cosmetic Applications Using Polyol-Based Technology

Published on: August 23, 2024

Clinical evidence for polyol efficacy.

P Milgrom¹, E M Söderling, S Nelson

¹University of Washington, Box 357475, B-509 Health Sciences, University of Washington, Seattle, WA 98195-7475, USA. dfrc@u.washington.edu

Advances in Dental Research

|August 18, 2012

Summary

This summary is machine-generated.

Xylitol effectively prevents dental caries in children when mothers use it during pregnancy or after birth. Habitual use of xylitol in gums or confections also helps reduce cavity-causing bacteria like Streptococcus mutans.

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Area of Science:

Oral Health
Preventive Dentistry
Microbiology

Background:

Dental caries remains a significant global health issue.
Xylitol and other polyols are recognized for their potential in caries prevention.
Research since 2008 has focused on xylitol's efficacy and transmission prevention.

Purpose of the Study:

To review and assess scientific literature on xylitol and polyols for dental caries prevention since 2008.
To evaluate xylitol's role in preventing early-life caries transmission.
To identify ongoing research and future directions in polyol-based caries prevention.

Main Methods:

Systematic review and assessment of published studies on xylitol and polyols.
Analysis of randomized controlled trials focusing on caries outcomes.
Evaluation of studies investigating maternal xylitol use and offspring caries risk.

Main Results:

Maternal xylitol use (lozenges, gum) prenatally or postnatally reduces caries transmission and incidence in offspring.
Xylitol gummy bears reduced Streptococcus mutans levels in schoolchildren.
Daily xylitol toothpaste use did not show significant S. mutans reduction in one study.

Conclusions:

Xylitol is a safe and effective agent for preventing dental caries, particularly when used habitually.
Maternal xylitol supplementation is a promising strategy to prevent early childhood caries.
Further systematic research is needed to fully understand the role of xylitol and other polyols in combating global dental caries.