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Organic Chemistry

6.1 Kinds of Organic Reactions

Organic Chemistry6.1 Kinds of Organic Reactions

6.1 • Kinds of Organic Reactions

Organic chemical reactions can be organized broadly in two ways—by what kinds of reactions occur and by how those reactions occur. Let’s look first at the kinds of reactions that take place. There are four general types of organic reactions: additions, eliminations, substitutions, and rearrangements.

  • Addition reactions occur when two reactants add together to form a single product with no atoms “left over.” An example that we’ll be studying soon is the reaction of an alkene, such as ethylene, with HBr to yield an alkyl bromide.
    The two reactants ethylene (an alkene) and hydrogen bromide react to form one product: bromoethane (an alkyl halide).
  • Elimination reactions are, in a sense, the opposite of addition reactions. They occur when a single reactant splits into two products, often with the formation of a small molecule such as water or HBr. An example is the acid-catalyzed reaction of an alcohol to yield water and an alkene.
    A reversible reaction shows the single reactant ethanol (an alcohol) in the presence of acid catalyst forming two products: ethylene (an alkene) and water.
  • Substitution reactions occur when two reactants exchange parts to give two new products. An example is the reaction of an ester such as methyl acetate with water to yield a carboxylic acid plus an alcohol. Similar reactions occur in many biological pathways, including the metabolism of dietary fats.
    The two reactants methyl acetate (ester) and water in the presence of acid catalyst form two products: acetic acid (a carboxylic acid) and methanol (an alcohol).
  • Rearrangement reactions occur when a single reactant undergoes a reorganization of bonds and atoms to yield an isomeric product. An example is the conversion of dihydroxyacetone phosphate into its constitutional isomer glyceraldehyde 3-phosphate, a step in the glycolysis pathway by which carbohydrates are metabolized.
    The single reactant dihydroxyacetone phosphate reacts to form a single isomeric product, glyceraldehyde 3-phosphate.
Problem 6-1
Classify each of the following reactions as an addition, elimination, substitution, or rearrangement:
(a)
CH3Br + KOH CH3OH + KBr
(b)
CH3CH2Br H2C = CH2 + HBr
(c)
H2C = CH2 + H2 CH3CH3
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