In the following posts, we will learn about the main reactions of alcohols. Each post is accompanied by practice problems of alcohol reactions to show the transformations and their corresponding mechanisms. The practice problems include simple one-step transformations such as the preparation of alcohols by reductions reactions of carbonyl compounds using NaBH4, LiAlH4, Pd/C, DIBAL-H and many more, as well as the oxidation of the alcohols to convert them into aldehydes, ketones and carboxylic acids depending on the reagent that is used. All the major oxidizing agents such as Na2Cr2O7/ H2SO4, H2CrO4, CrO3/ H+, KMnO4/ -OH/ H+, NaClO/AcOH. will also be discussed.
We will also discuss in detail how alcohols react in substitution and elimination reactions. This will include the reactions where alcohols are used as a substrate and also reactions where they work as the base and the nucleophile.
The Grignard Reaction used for the synthesis of alcohols and in general, the application of the Grignard Reaction in Organic Synthesis is also covered in many examples. To be used in organic synthesis, the hydroxyl group often needs to be protected in the presence of strong bases like organometallics. The protecting groups of alcohols and strategies for their use organic synthesis are also covered with a handful of practice problems.
Pyridinium Chlorochromate (PCC) Oxidation PCC oxidation is one of the selective methods for oxidizing primary alcohols to aldehydes. Although very often the outcome of the oxidation will depend on the presence or absence of water, traditionally, the most common mild oxidizing … Read more
Swern oxidation is one of the selective methods for oxidizing primary alcohols to aldehydes. Like other mild oxidizing agents, such as pyridinium chlorochromate (PCC), pyridinium dichromate (PDC), and the Dess-Martin (DMP) oxidation, it stops the oxidation once the carbonyl group … Read more
Dehydration of alcohols using phosphorus oxychloride (POCl3) and pyridine (an amine base) in place of H2SO4 or TsOH is a good alternative for converting alcohols to alkenes when working with compounds that decompose in the presence of strong acids: … Read more
Alcohols can be oxidized into a variety of carbonyl compounds depending on the nature of the alcohol and the oxidizing agent used. Secondary alcohols can only be oxidized to ketones, while primary alcohols are oxidized to aldehydes and carboxylic acids, … Read more
Why do you think the following Grignard reaction is impossible to carry out without having a protecting group on the alcohol? What is even a protecting group? These are the questions we are going to address in today’s article. … Read more
The main difference of the Grignard reaction compared to everything else you learn in the reactions of alcohols is that it is another way of making a new C-C bond and extending the carbon chain of the molecule. The most … Read more
In this post, we will talk about the Grignard reaction – a fundamental reaction in organic chemistry discovered by Victor Grignard in 1912, which gave him the Nobel Prize. The most common and important Grignard reaction is the one with … Read more
Alcohols can be prepared by reduction of aldehydes, ketones, esters and other carbonyl containing compounds. There are dozens of reagents such as LiAlH4, BaBH4, DIBAL for reducing carbonyls to alcohols. Each of these reagents has advantages and disadvantages. Some are … Read more
Preparation of Alcohols from Alkyl Halides Alcohols can be prepared by substitution reactions using hydroxides and substrates with good leaving groups, such as alkyl halides. Primary substrates react by the SN2 mechanism, while tertiary substrates undergo SN1 reactions when strong … Read more
Naming alcohols follows the same rules we discussed earlier for the IUPAC nomenclature rules for alkanes. This is the brief summary of the steps: Step 1. Identify the parent chain. Step 2. Identify the substituents. Step 3. Number the parent chain, giving … Read more
