The only way of mastering any topic in Organic Chemistry is doing lots of practice problems. And I know, seeing my students, that starting to work on a practice problem may be the hardest part as you don’t know where to start. It is difficult to visualize what where the double bond would be moved if you follow the five curved arrows crammed in one step. Here is the trick:
We are always told to think before doing something. Fair enough. But let me tell you, it is also strangely enough, that in Organic Chemistry, it is often better to draw and then think about what you did (not in the lab though). It is much easier to have a structure in front of you and check for errors and improvements.
Do the first step, take the pencil and you will see that the ball gets rolling.
You have all these Organic Chemistry Practice Problems waiting to be solved!
The reaction of aldehydes and ketones with secondary amines produces enamines. Enamines are amines with a double bond on the adjacent carbon (alkene + amine = enamine): Let’s go over the mechanism of this transformation to see how … Read more
Aldehydes and ketones react with primary amines, in mildly acidic conditions, forming an imine (a Schiff base). The reaction with secondary amines produces enamines: Just like the reaction with water and alcohols, this is also an addition reaction … Read more
Naming a compound with more than one functional group is not as straightforward as it is for alkanes, alkyl halides, or alkenes. For example, how do you name a molecule that contains a nitrile and a ketone? If … Read more
Alcohols can be prepared from carbonyl compounds such as aldehydes, ketones, esters, acid chlorides, and even carboxylic acids by hydride reductions. These reductions are a result of a net addition of two hydrogen atoms to the C=O bond: … Read more
We have seen many times when discussing the SN2 mechanism that ethers are common products of nucleophilic substitution reactions. They are synthesized by reacting alkyl halides or other substrates with good leaving groups with alkoxides: This method of … Read more
Alcohols can be converted to alkyl halides by reacting with HX (X = Cl, Br, I) acids. The reaction works for 1°, 2°, and 3° alcohols: Let’s now understand how this happens. We have seen many times in … Read more
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
Thionyl chloride (SOCl2) and phosphorus tribromide (PBr3) can be used for converting primary and secondary alcohols to alkyl chlorides and alkyl bromides respectively: Both reactions have similar mechanisms with the idea of turning the OH into a good … Read more
Dess–Martin periodinane (DMP) oxidation Alcohols can be oxidized to aldehydes, ketones, and carboxylic acids depending on their structure and the type of oxidizing agent. In general, we can classify oxidizing agents as strong and mild. Mild oxidizing reagents stop the … Read more
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
