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Other compounds may also be involved, and common reactive partners reagents may be identified. The reactant is often but not always the larger and more complex molecule in the reacting system. Most or all of the reactant molecule is normally incorporated as part of the product molecule. Reagent: A common partner of the reactant in many chemical reactions.

It may be organic or inorganic; small or large; gas, liquid or solid. The portion of a reagent that ends up being incorporated in the product may range from all to very little or none. Product s The final form taken by the major reactant s of a reaction. Catalysts are substances that accelerate the rate velocity of a chemical reaction without themselves being consumed or appearing as part of the reaction product. Catalysts do not change equilibria positions. Reaction Classification. If you scan any organic textbook you will encounter what appears to be a very large, often intimidating, number of reactions.

Organic chemistry | Science | Khan Academy

These are the "tools" of a chemist, and to use these tools effectively, we must organize them in a sensible manner and look for patterns of reactivity that permit us make plausible predictions. Most of these reactions occur at special sites of reactivity known as functional groups , and these constitute one organizational scheme that helps us catalog and remember reactions. Ultimately, the best way to achieve proficiency in organic chemistry is to understand how reactions take place, and to recognize the various factors that influence their course. This is best accomplished by perceiving the reaction pathway or mechanism of a reaction.

First, we identify four broad classes of reactions based solely on the structural change occurring in the reactant molecules. This classification does not require knowledge or speculation concerning reaction paths or mechanisms. The letter R in the following illustrations is widely used as a symbol for a generic group. It may stand for simple substituents such as H— or CH 3 —, or for complex groups composed of many atoms of carbon and other elements. The reverse is true of elimination reactions, i. Substitution reactions, as the name implies, are characterized by replacement of an atom or group Y by another atom or group Z.

Aside from these groups, the number of bonds does not change.

Organic chemistry

A rearrangement reaction generates an isomer, and again the number of bonds normally does not change. The examples illustrated above involve simple alkyl and alkene systems, but these reaction types are general for most functional groups, including those incorporating carbon-oxygen double bonds and carbon-nitrogen double and triple bonds.


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Some common reactions may actually be a combination of reaction types. The addition of water to a nitrile does not seem to fit any of the above reaction types, but it is simply a slow addition reaction followed by a rapid rearrangement, as shown in the following equation. Rapid rearrangements of this kind are called tautomerizations. Additional examples illustrating these classes of reaction may be examined by Clicking Here.

At the beginning, it is helpful to identify some common reaction types that will surface repeatedly as the chemical behavior of different compounds is examined. This is not intended to be a complete and comprehensive list, but should set the stage for future elaborations. It is useful to begin a discussion of organic chemical reactions with a review of acid-base chemistry and terminology for several reasons.

First, acid-base reactions are among the simplest to recognize and understand. Second, some classes of organic compounds have distinctly acidic properties, and some other classes behave as bases, so we need to identify these aspects of their chemistry. In an acid-base reaction, each side of the equilibrium has an acid and a base reactant or product, and these may be neutral species or ions. Substances that can serve as both acids and bases, such as water, are termed amphoteric. The relative strength of a group of acids or bases may be evaluated by measuring the extent of reaction that each group member undergoes with a common base or acid.

Water serves nicely as the common base or acid for such determinations. Thus, for an acid H-A, its strength is proportional to the extent of its reaction with the base water, which is given by the equilibrium constant K eq. Since these studies are generally extrapolated to high dilution, the molar concentration of water The resulting K value is called the acidity constant , K a. Clearly, strong acids have larger K a 's than do weaker acids.

Addition Reactions

Because of the very large range of acid strengths greater than 10 40 , a logarithmic scale of acidity pK a is normally employed. Stronger acids have smaller or more negative pK a values than do weaker acids. In all the above examples water acts as a common base. The last example NH 3 cannot be measured directly in water, since the strongest base that can exist in this solvent is hydroxide ion.


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Consequently, the value reported here is extrapolated from measurements in much less acidic solvents, such as acetonitrile. Since many organic reactions either take place in aqueous environments living cells , or are quenched or worked-up in water, it is important to consider how a conjugate acid-base equilibrium mixture changes with pH. A simple relationship known as the Henderson-Hasselbalch equation provides this information. When the pH of an aqueous solution or mixture is equal to the pK a of an acidic component, the concentrations of the acid and base conjugate forms must be equal the log of 1 is 0.

Course summary

Consequently, mixtures of acidic and non-acidic compounds are easily separated by adjusting the pH of the water component in a two phase solvent extraction. The ether solution of the alcohol may then be separated from the water layer, and pure alcohol recovered by distillation of the volatile ether solvent. The pH of the water solution of sodium benzoate may then be lowered to 1. For a discussion of how acidity is influenced by molecular structure Click Here.

The basicity of oxygen, nitrogen, sulfur and phosphorus compounds or ions may be treated in an analogous fashion. Thus, we may write base-acid equilibria, which define a K b and a corresponding pK b. However, a more common procedure is to report the acidities of the conjugate acids of the bases these conjugate acids are often "onium" cations. The pK a 's reported for bases in this system are proportional to the base strength of the base. We see this relationship in the following two equilibria:.

Tables of pK a values for inorganic and organic acids and bases are available in many reference books, and may be examined here by clicking on the appropriate link: Inorganic Acidity Constants Organic Acidity Constants Basicity Constants. Although it is convenient and informative to express pK a values for a common solvent system usually water , there are serious limitations for very strong and very weak acids.

Solvents such as acetic acid, acetonitrile and nitromethane are often used for studying very strong acids. Relative acidity measurements in these solvents may be extrapolated to water. Likewise, very weakly acidic solvents such as DMSO, acetonitrile, toluene, amines and ammonia may be used to study the acidities of very weak acids.

For both these groups, the reported pK a values extrapolated to water are approximate, and many have large uncertainties. Look out for the following: What functional group is present on the reactant?

What functional group is present on the product? Which reactions do I know to convert from one to the other? Go through your questions: What functional group is present on the reactant? Reactive terminal alkyne What functional group is present on the product? Ketone on carbon 2 Which reactions do I know to convert from one to the other? But wait, the product is an enol, not a ketone!! And there we have it! As in, where do I start the mechanism?

In fact, I challenge you to give this a try and see how far you get before reading on. Propose a reasonable mechanism for the following reaction.


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Show all intermediates and formal charges.