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NH. H. (100%) N. ". . . after ca. 10 seconds, a relatively violent reaction occurred which was accompanied by a dense cloud of white smoke and change in color from the characteristic yellow-green of the starting material to a dark brown."
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The Sommelet-Hauser rearrangement may simply be defined as the rearrangement reaction of certain benzyl quaternary ammonium salts where the reagent used is sodium amide (or alkali amide) and the reaction results in the N,N-dialkylbenzylamine with a new alkyl substituent in the aromatic o-position. Now because the final product is a benzylic ...
- Rearrangement Reactions
- Nucleophilic Substitution Accompanied by Rearrangement
- Alkene Addition Accompanied by Rearrangement
- Elimination (E1) Accompanied by Rearrangement
Rearrangement reactions can accompany many of the reactions we’ve previously covered such as substitution, addition, and elimination reactions. 1. Substitution (SN1) (See post: Alkyl Halides From Alcohols) 2. Elimination (E1) (See post: Elimination (E1) With Rearrangement) 3. Alkene addition reactions (See post: Rearrangements in Alkene Addition Re...
In fact, if you don’t look closely, sometimes you can miss the fact that a rearrangement reaction has occurred. Let’s look at a substitution reaction first. On the top is a “typical” substitution reaction: we’re taking an alkyl halide and adding water. The C-Br bond is broken and a C-OH bond is formed. If you look at the table on the right you’ll s...
Let’s look at another example, but involving an addition reaction (the addition of HCl to alkenes). Here we have an addition reaction. On top, nothing special – as with all additions, we break a C-C double bond (π bond )and form two new single bonds to the adjoining carbons (H and Cl). But look at the bottom example. If we use that alkene instead, ...
Finally, let’s look at an elimination reaction. If you take an alcohol like the one below and add an acid (like H2SO4, pictured) and help the reaction along with some heat, you break the C1-OH and C2-H bonds, and form a new double bond between C1-C2. This is, in other words, a typical elimination reaction. But if you take a slightly modified alcoho...
1 RearrangementReactions. 1. Rearrangement ReactionsA rearrangement reaction is a board class of organic reactions in which an atom, ion, group of atoms, or chemical unit migrates from one atom to another atom in the same or different species, resulting in a structural isomer o.
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Rearrangement reactions mostly involve breaking and/or making C—C, C—O, or C—N bonds. The migration origin is the atom from which the group moves, and the migration terminus is the atom to which it migrates. This chapter discusses the mechanism, experimental procedure, and applications of various rearrangement reactions, namely Baeyer ...
Benzilic Acid Rearrangement. The benzilic acid rearrangement involves conversion of a 1,2-diketone into a carboxylic acid. The conditions are deceptively simple, hydroxide followed by an acid quench, and lead to the migration of a benzene ring. This mechanism is relatively straightforward.
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Bonding MO Antibonding MO. σ = C1ψ1 + C2 ψ2 σ* = (C1*)ψ1 + (C 2*) ψ. 2. The coefficients C1 and C2 represent the contribution of each AO. The squares of the C-values are a measure of the electron density on the atoms in question. Rule 3: Both wave functions must contribute one net orbital. Consider the C-O pi-bond.
