LiAlH4, NaBH4, DIBAL Reduction Summary for Aldehydes, Ketones, Esters and carboxylic Acids
LiAlH4 NaBH4 DIBAL reduction summary for aldehydes, ketones, esters, carboxylic acids and acid chlorides
3 Factors That Stabilize Carbocations
Three main factors increase the stability of carbocations: Increasing the number of adjacent carbon atoms (methyl < primary < secondary < tertiary (most stable) Adjacent pi bonds that allow the carbocation p-orbital to be part of a conjugated pi-system system ("delocalization through resonance") Adjacent atoms with lone pairs More details below.
Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions
Time is precious. Drawing the full structures of chemical formulae out is a gigantic pain. From a distance, maybe an extra 10-20 seconds here or
The Mechanism of Organolithium Reaction with Nitriles
Both Grignard and organolithium reagents can be used to convert nitriles to ketones. The new C-C bonds are formed by nucleophilic addition of the organometallic reagents to the polar C-N triple bond. After protonation of the resulting anion, ... Read more
What Makes a Good Leaving Group in Nucleophilic Substitution and Elimination Reactions
A Good Leaving Group is a must for a Nucleophilic Substitution or Elimination Reaction to occur. The good leaving group is a conjugate base of a strong acid. This trend is summarized in the following chart.
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Five and Six-Membered Rings are Favorable in Intramolecular Aldol Reactions
If a compound has two carbonyl groups (dicarbonyl compound), it undergoes an intramolecular aldol reaction if a five- or six-membered ring can be formed: What happens is one of the carbonyls is deprotonated at the ɑ position, thus ... Read more
Retrosynthetic Analysis in Robinson Annulation
In the previous post, we talked about the Michael reaction which is a conjugate-addition reaction of doubly stabilized enolates such as malonic ester, acetoacetic ester and the like with ɑ, β-unsaturated carbonyl compounds: One important variation of the ... Read more
Enols and Enolates Summary Sheet for Alpha Carbon Chemistry
Summary Cheat Sheets Study Guides for Organic Chemistry 1 and 2. Comprehensive, beautifully crafted powerful summary cheat sheets in high-resolution PDF.
Alpha halogenation of enols and enolates practice problems
In the previous post, we talked about the alpha halogenation of aldehydes and ketones and its application in organic synthesis. So, if you already went over this material, go ahead and work on these practice problems. The second part involves ... Read more
Reactions of Epoxides Practice Problems - Predicting the Product
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.