In the following posts, we will learn about and do many practice problems on Nucleophilic Substitution Reactions. Nucleophilic Substitution Reactions are one of the most important major classes of organic chemistry and essential that you build a solid foundation and understanding of their principles and mechanisms such as the SN1 and SN2 reactions.
We will start from the introduction and general features of Nucleophilic Substitution Reactions and go in detail individually for the SN1 and SN2 mechanism. Each practice problem is designed to address the specifics of these mechanisms; the reactivity, stereochemistry and possibility of rearrangements. For example, you will have many practice problem examples that demonstrate in detail the inversion of R and S configuration during SN2 reactions. On the other hand, we will also see why a racemic mixture is obtained when the reaction goes by the SN1 mechanism via the formation of a carbocation intermediate.
One important and yet overwhelming questions in Nucleophilic Substitution Reactions is the prediction of the mechanism as to whether it is SN1 or SN2. And we will talk about how to choose between SN1 and SN2 considering the nucleophile, the substrate, the solvent, and the reaction conditions. Once you have sufficient knowledge, we will so do the retrosynthetic analysis of Nucleophilic Substitution Reactions to learn the best of choosing a reagent for functional group transformations.
In this post, we’ll talk about a common question you encounter in organic chemistry tests and exams. How do you know if the alkyl halide or a similar substrate will react by SN1 or E1 mechanism? This dilemma is one … Read more
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In the previous post, we discussed ring expansion rearrangements where 4 and 5-membered rings were transformed into more stable larger rings. Sometimes, the process goes in reverse direction, and larger rings are transformed into smaller rings. These are … Read more
Let’s address two common exam questions: comparing the SN2 and E2 rates of two isomeric cyclohexanes and determining the major product in those reactions. The first thing you need to remember here is that both SN2 and E2 … Read more
There are several ways of converting alcohols to alkyl halides. The most common, and perhaps the one that covers nuances of SN1 and SN2 reactions is the use of HX acids (HCl, HBr, HI), so let’s start with that. The … Read more
Let’s discuss some strategies for converting alkyl halides to aldehydes and ketones. Converting the alkyl halide to an alcohol and oxidizing the latter to an aldehyde or ketone requires the least number of topics to have covered, so let’s start … Read more
Alkyl halides can be converted to alcohols by reacting them with water or hydroxide ion. Recall that the hydroxide ion is a good nucleophile, and water is a poor nucleophile; therefore, the conversions occur via SN2 and SN1 mechanisms, respectively. … Read more
Ring Strain and Ring Expansion The title of today’s discussion contains two keywords: Ring Expansion and Rearrangement. So, what are those? A ring expansion is the transformation of a smaller ring to a larger ring. A rearrangement is a change … Read more
The SN1 mechanism is a unimolecular process, which means only the substrate participates in the rate-determining step of the reaction. The rate-determining step is the loss of the leaving group, which forms a carbocation. There are a few main features … Read more
Alkyl halides react with water by SN1 mechanism forming alcohols. Let’s put together some examples of these hydrolysis reactions of alkyl halides and address some important concepts such as the mechanisms, stereochemistry, the relationship of products, and different types of … Read more
