Chemmunity Team 

3. DMP (Dess-Martin Periodinane)

Reagents: Uses Dess-Martin periodinane, which is an iodine-based oxidizing agent.

Conditions: Very mild and efficient, often used at room temperature.

Products:

Primary alcohols → Aldehydes.

Secondary alcohols → Ketones.

Selectivity: Like the others, it’s selective and stops at the aldehyde stage for primary alcohols. It does not oxidize further to carboxylic acids.

Advantages: DMP is known for being user-friendly and producing fewer byproducts compared to chromium-based reagents like PCC.

1. Swern Oxidation

Reagents: Uses dimethyl sulfoxide (DMSO), oxalyl chloride, and a base like triethylamine.

Conditions: Mild and performed at low temperatures (around -78°C).

Products:

Primary alcohols → Aldehydes.

Secondary alcohols → Ketones.Selectivity: It’s selective and does not over-oxidize primary alcohols to carboxylic acids. It stops at the aldehyde stage.

2. PCC (Pyridinium Chlorochromate)

Reagents: PCC is a chromium-based oxidizing agent, often used with a solvent like dichloromethane (DCM).

Conditions: Mild and does not require extreme temperatures.

Products:

Primary alcohols → Aldehydes.

Secondary alcohols → Ketones.

Selectivity: PCC is also selective and stops at the aldehyde stage for primary alcohols. It does not oxidize further to carboxylic acids, unlike chromic acid 

This goes back to the template shown at 10:58 under the both together text. Think of this as your template of all the possible equatorial and axial positions. Then looking at the given cyclohexane you look at the attached substituents, you also number the chain and apply this to the chair. 

There are multiple possibilities but remember the one with the most equatorial positions is the best and if there is a tie then pick the one that has the bulkier group in the equatorial position. 

There's another example of this in the below video it's question 3 at timestamp 14:34.

At 10:58 of this video Melissa shows you how to tell what is going up or down using her arrow trick. If you were to draw an arrow away from the chair so in the direction of the substituent this will tell you if it is up or down. Use the drawn model under both together as a template of where the typical points and drawings look like. 

I also recommend watching the below video for more practice, it will help you understand this a lot more! 

Hey Michelle, if you haven't already done so, I recommend watching the below video. This goes over all the different formulas and ways to draw structures in Organic Chemistry and will give you the visuals you need to further understand this. 

We have added the functional groups list Melissa used in this video to the downloadable pdfs. You'll find that under the video's description. 

We have added the functional groups list Melissa used in this video to the downloadable pdfs. You'll find that under the video's description. 

R1 and R2 mean they are two different alkyl groups. You can also see this shown as R and R' and R"

R means the rest of the carbon chain, so when you see an R there it means there's a substituent made up of only C and H, this is referred to as alkyl groups.

Thank you Vanessa! We are happy you are here and that you are loving the Study with us series :)