Introduction to Rearrangement Reactions
…resulting in breakage and formation of a C-H or C-C bond, and formation of a new carbocation. The new carbocation (generally more stable) then undergoes a second reaction to give…
Read more…resulting in breakage and formation of a C-H or C-C bond, and formation of a new carbocation. The new carbocation (generally more stable) then undergoes a second reaction to give…
Read more…Example 4 is an Oxy-cope reaction, which forms an enol that then tautomerizes to an aldehyde. The last example shows an Oxy-Cope where a new 10-membered ring is formed. Mechanism:…
Read more…to “what happens” is a prerequisite to being able to answer “how it happens”, or “why it happens”. And it’s a completely learnable skill. It’s a skill that someone could…
Read more…by about 20 kcal/mol, owing mostly to the greater strength of C-O (pi) bonds (80 kcal/mol) versus C-C (pi) bonds (60 kcal/mol). Examples: Notes: In the first two examples, heating…
Read more…intramolecular version. It involves no new concepts, but it looks weird, and for this reason intramolecular reactions make for good exam problems. In this case a cyclic ester, called a…
Read more…The purpose of H3O+ at the end is to protonate the negatively charged oxygen. Examples: Notes: Each of these four examples show the addition of two equivalents of an organolithium…
Read more…more or less random examples I pulled off the top of my head: These are further examples of concepts, or relationships between properties. If you look at practice exam problems,…
Read more…bromine like N-bromosuccinimide (NBS). Various acids can be used (e.g. HBr, acetic acid (AcOH). Examples: Notes: Example 1 shows formation of a new C-Br bond using HBr and Br2. Example…
Read more…formal charge) Common Mistakes: Formal Charges Can Mislead A Key Skill: How to Calculate Formal Charge Nucleophiles and Electrophiles The Most Important Question To Ask When Learning a New Reaction…
Read more…Examples 2 and 3 show CBz protection. Example 4 shows a Boc deprotection of the amine under acidic conditions which leaves the CBz protected amine unaffected. Example 5 shows removal…
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