We have seen that carbocation rearrangements may lead to unexpected products in SN1 nucleophilic substitution reactions. For example, when the following alkyl halide is reacted with water, the major product of the reaction is formed via a hydride shift, which … Read more
Let’s make an overview of elimination reactions in organic chemistry. The first question we want to address is: What is eliminated from the molecule?While there may be different atoms removed in elimination reactions, most of the time it involves the … Read more
In this post, we will practice E2 elimination reactions, focusing on the mechanism and how to determine the major and minor products based on the structure of the substrate and the nature of the base. Common bases we will consider … Read more
In an antiperiplanar arrangement, two atoms or groups are positioned on opposite sides of the same plane, typically around a carbon-carbon single bond. This is clearly seen in the Newman projection of butane, where the lowest-energy anti conformation places the … Read more
Let’s first reveal who this t-BuOK that you see every day is: t-BuOK stands for potassium tert-butoxide, which is the conjugate base of tert-butanol. It features a negatively charged oxygen bonded to a tertiary carbon, making t-BuOK a strong but … Read more
Carbocations are electron-deficient species, as the carbon atom is surrounded by only three bonds with no lone pairs. Remember, the standard bonding pattern of carbon is 4 bonds with no lone pair: So, how can we stabilize the … Read more
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
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
The dehydrohalogenation of alkyl halides gives alkenes. For example, we can react alkyl halides with strong bulky and non-bulky bases to prepare the Zaitsev or Hofmann alkene: Preparation of Alkynes As the name suggests, in these dehydration reactions, … Read more
