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For aliphatic carbon-halogen bonds, the C-F bond is the strongest and usually less chemically reactive than aliphatic C-H bonds. The other aliphatic-halogen bonds are weaker, their reactivity increasing down the periodic table. They are usually more chemically reactive than aliphatic C-H bonds. As a consequence, the most common halogen ...
In organic chemistry, neighbouring group participation (NGP, also known as anchimeric assistance) has been defined by the International Union of Pure and Applied Chemistry (IUPAC) as the interaction of a reaction centre with a lone pair of electrons in an atom or the electrons present in a sigma or pi bond contained within the parent molecule but not conjugated with the reaction centre.
Carbonyl, thiocarbonyl-, and selenocarbonyl groups, with a trigonal planar geometry around the Lewis donor atom, can accept one or two halogen bonds. [16] Anions are usually better halogen-bond acceptors than neutral species: the more dissociated an ion pair is, the stronger the halogen bond formed with the anion. [17]
To form five bonds, the one s, three p and one d orbitals combine to form five sp 3 d hybrid orbitals which each share an electron pair with a halogen atom, for a total of 10 shared electrons, two more than the octet rule predicts. Similarly to form six bonds, the six sp 3 d 2 hybrid orbitals form six bonds with 12 shared electrons. [18]
Acyl substitution occurs when a nucleophile attacks a carbon that is doubly bonded to one oxygen and singly bonded to another oxygen (can be N or S or a halogen), called an acyl group. The nucleophile attacks the carbon causing the double bond to break into a single bond. The double can then reform, kicking off the leaving group in the process.
EWGs enhance the Lewis acidity, making compounds more reactive as Lewis acids. For example, fluorine is a stronger electron-withdrawing substituent than methyl, resulting in an increased Lewis acidity of boron trifluoride relative to trimethylborane. Electron-withdrawing groups also tend to reduce Lewis basicity. [3]
Aliphatic compounds can be saturated, joined by single bonds (), or unsaturated, with double bonds or triple bonds ().If other elements (heteroatoms) are bound to the carbon chain, the most common being oxygen, nitrogen, sulfur, and chlorine, it is no longer a hydrocarbon, and therefore no longer an aliphatic compound.
The carbon on that is sp 3 hybridized and less electronegative than those that are sp 2 hybridized. They have overlap on the carbon–hydrogen bonds (or carbon–carbon bonds in compounds like tert-butylbenzene) with the ring p orbital. Hence they are more reactive than benzene and are ortho/para directors.