Markovnikov’s Rule In the previous post, we talked about the addition reaction of hydrogen halides (HCl, HBr, and HI) to alkenes, and learned about Markovnikov’s rule, which states that in these reactions, the halogen adds to the more substituted carbon … Read more
Preparation of Aniline There are a few main ways of preparing aniline: Reduction of the Nitro Group We can add a nitro group to benzene or its derivative via a standard nitration using HNO3 and H2SO4, and then reduce the … Read more
When 1,2-diols (vicinal diols) are treated with acid, a rearrangement takes place, and the diol is transformed to a ketone. This reaction is known as the pinacol rearrangement since pinacol is the simplest diol capable of undergoing such … Read more
Epoxides are three-membered rings containing an oxygen atom. They are associated with high ring strain, and this is the basis of their reactivity towards nucleophiles despite lacking a good leaving group. The ring strain is a combination of two destabilizing factors: angle … Read more
In the previous post, we discussed the ring-opening reactions of epoxides with strong and weak nucleophiles. Using this information, try solving the following practice problems.
Remember when discussing the substitution reactions, we said that the hydroxide ion (–OH) is a poor leaving group since it is quite a strong base. Therefore, the –OH cannot be expelled by a direct nucleophilic attack in an SN2 or … Read more
This is a comprehensive problem that covers the following topics and will serve as a review of all of them: Substitution and elimination reactions. Particularly, substitution and elimination reactions of alcohols, the regio– and stereochemistry of E2 reactions and E2 reaction … Read more
Now that you have learned about the SN1 and SN2 mechanisms, try to draw a reasonable mechanism for the following substitution reaction: Wait, this doesn’t make sense, right? The nucleophile suddenly appears where there was no leaving group… … Read more
