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Introduction to Reaction Classification by Reaction Type

In the starting, it is useful to identify some general reaction types that will surface repeatedly as the chemical behaviour of different compounds is examined. This is not intended to a comprehensive and complete list, but should set stage for the future explanations.

Acidity and Basicity

The discussion of organic chemical reactions it is useful to start with a review of acid-base chemistry and terminology for several reasons. First reason is, the reactions that are based on acid are among the simplest to understand and recognize. 2nd some classes of organic compounds behave like bases where as some other classes have distinctly acidic properties, so we need to recognize these aspects of their chemistry. By acids and/or bases many organic reactions are catalyzed, and although this type of transformations may seem complex, our understanding of how they occur often starts with the functioning of the catalyst.

An organic chemist uses two acid-base theories for interpreting and planning their work: the Brønsted theory and the Lewis theory.

Brønsted Theory

As per the Brønsted theory the proton donor is known as an acid and proton acceptor is known as base. In the reactions that are based on acid, each side of the equilibrium has an acid and a base reactant or product and these may be neutral species or ions.

    H-A   +   B:(-)            ↔            A:(-)   +   B-H

(acid)     (base)                        (base)     (acid)

Conjugate pairs are Structurally related acid-base pairs, like {B:(-) and B-H} or {H-A and A:(-)} . amphoteric are the substances that can serve as both the acids and bases, like water.

 H-Cl   +   H2O       ↔     Cl:(-)   +   H3O(+)

(Acid)     (Base)             (Acid)     (Base)

 

 H3N:   +   H2O       ↔    NH4(+)   +   HO(-)

(Base)     (Acid)             (Acid)       (Base)

The strength of a group of acids (or bases) may be calculated by measuring the extent of reaction that every group member goes through the common base (or acid). The Water serves properly as the common base or acid for this type of determinations. So, for an acid H-A, its strength is proportional to the extent of its reaction with the base water, which is given by equilibrium constant Keq.

H-A   +   H2O           ↔           H3O(+)   +  A:(-)                  580_Reaction Classification by Reaction Type Homework Help.jpg

Since these studies are usually extrapolated to high dilution, water's molar concentration is constant and may eliminate from the denominator. The acidity constant is the Resulting K value, Ka. Clearly, weaker acids have smaller Ka's than the strong acids. Due to the very large range of acid strengths (greater than 1040), a logarithmic scale of acidity (pKa) is normally employed. Stronger acids have smaller or more negative pKa values than do weaker acids.

2184_Reaction Classification by Reaction Type Homework Help 1.jpg

Oxidation and Reduction Reactions

A parallel and independent method of characterizing organic reactions is by oxidation-reduction terminology. Carbon atoms may consist any oxidation state from -4 (e.g. CH4 ) to +4 (e.g. CO2 ), depending on their substituents. Fortunately, we need not to determine the absolute oxidation state of every carbon atom in a molecule, but only change in oxidation state of those carbons involved in a chemical transformation. for determine whether a carbon atom has undergone a redox change during a reaction we just note any variation in the number of bonds to hydrogen and the number of bonds to more electronegative atoms like O, N, F, Cl, Br, I, & S that has occurred. Bonds to the other carbon atoms are ignored. This count should be conducted for the each carbon atom undergoing any change throughout a reaction.

  1. If the number of hydrogen atoms that are bonded to a carbon get increased, and/or if number of bonds to more electronegative atoms get decreased, carbon in question has been reduced (i.e. it is in a lower oxidation state).
  2. If the number of hydrogen atoms bonded to a carbon get decreased, and/or if number of bonds to more electronegative atoms get increased, the carbon in the question has been oxidized (i.e. it is in a higher oxidation state).
  3. If there has been no change in the number of this type of bonds, then the carbon in question has not changed its oxidation state. In a nitrile's hydrolysis reaction that is shown above, blue colored carbon has not changed its oxidation state.

These rules are demonstrated by the following four addition reactions involving similar starting material, cyclohexene. The Carbon atoms colored red are oxidized and those colored blue are reduced. In addition to the hydrogen both carbon atoms are get reduced and overall reaction is termed a reduction. The Peracid epoxidation and addition of bromine oxidize both carbon atoms, so these are the termed oxidation reactions. Addition of the HBr reduces one of the double bond carbon atoms and oxidizes the other; consequently, there is no overall redox change in substrate molecule.

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