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Chapter-2: Reactions of Organic Compounds

There are 3 main types of Organic Reactions: Addition reactions; Substitution reactions; and Elimination reactions Most organic reactions can be classified as one of these three types.

Addition Reactions
I an addition reaction, atoms are added to a double In dditi ti t dd d t d bl or triple bond. One bond of the multiple bond breaks so that two new bonds can form. To recognize an addition reaction, remember that two compounds usually react to form one major product. (Sometimes two isomers are formed.) The d t (S ti t i f d ) Th product has more atoms bonded to carbon atoms t a the organic eacta t did. dd t o eact o s are than t e o ga c reactant d d Addition reactions a e common for alkenes and alkynes. Addition reactions can also occur at a CO bond. Some examples of addition reactions are shown on S l f dditi ti h the next slide.

AdditionReaction: Reactant+Reactant Product

Doublebond D bl b d

SingleBonds Si l B d

Substitution Reactions
I a substitution reaction, a h d In b tit ti ti hydrogen atom or a t functional group is replaced by a different functional g group. p To help you recognize this type of reaction, remember that two compounds usually react to form two diff t different products. The organic reactant(s) and t d t Th i t t( ) d the organic product(s) have the same number of ato s bonded ca bo atoms bo ded to carbon. Alcohols, alkyl halides, and aromatic compounds commonly undergo substitution reactions, as shown in th i these examples. l

SubstitutionReaction: Reactant R Product P d +Reactant + Reactant +Product + Product

Elimination Reactions
In an elimination reaction atoms are removed from a reaction, molecule to form a double bond. This type of reaction is the reverse of an addition reaction. One reactant usually breaks up to give two products. The organic product typically has fewer atoms bonded to carbon atoms than the organic reactant did. Alcohols often undergo elimination reactions when they are heated in the presence of strong acids, such as sulfuric acid, H2SO4, which acts as a catalyst. (See the first example below ) Alkyl halides also undergo below.) elimination reactions to produce alkenes.

EliminationReaction: Reactant Product+Product

Oxidation and Reduction (Redox)

An important type of organic reaction occurs when there is a change in the number of hydrogen or oxygen atoms that are bonded to carbon. carbon As you will learn, oxidation and reduction always occur g together. One reactant is oxidized while the other reactant is reduced. In this section, however, you will focus on the organic reactant only. Th f Therefore, you will deal with oxidation and reduction ill d l ith id ti d d ti separately, as they apply to organic compounds. In organic chemistry, oxidation and reduction are defined by g y, y the changes of the bonds to carbon atoms in the organic reactant.

In I organic chemistry, oxidation i defined as a reaction i h i t id ti is d fi d ti in which a carbon atom forms more bonds to oxygen, O, or less bonds to hydrogen, H. An oxidation that , y g , involves the formation of double CO bonds may also be classified as an elimination reaction. For F example, alcohols can be oxidized to produce l l h l b idi d t d aldehydes and ketones. Oxidation occurs when an o ga c compound eacts t an o d organic co pou d reacts with a oxidizing agent. g age t Common oxidizing agents include acidified potassium permanganate, KMnO4, acidified potassium dichromate, K2Cr2O7, and ozone O3. dichromate K2Cr2O7 ozone, O3

The symbol [O] is used to symbolize an oxidizing agent. Note that equations for the oxidation of organic compounds are often left unbalanced The purpose unbalanced. of the equation is to show the changes in the organic reactant only. y To identify an oxidation, count and compare the number of CH and CO bonds in both the reactant and product. Try it for the following examples.

I organic chemistry, reduction i defined as a In i h i t d ti is d fi d reaction in which a carbon atom forms fewer bonds to oxygen, O, or more bonds to hydrogen, H. yg , , y g , Often, a CO bond or CC bond is reduced to a single bond by reduction. A reduction that transforms double d bl CC or CO bonds to single bonds may also be b d t i l b d l b classified as an addition reaction. Aldehydes ketones and carboxylic acids can be Aldehydes, ketones, reduced to become alcohols. Alkenes and alkynes can be reduced by the addition of H2 to become alkanes. R d ti lk Reduction occurs when an organic h i compound reacts with a reducing agent.

Common reducing agents are lithium aluminum hydride, LiAlH4, and hydrogen gas over a platinum catalyst, H2/Pt catalyst H2/Pt. The symbol [H] is used to symbolize a reducing agent. As is the case for oxidation, equations showing the reduction of organic q g g compounds are often left unbalanced. To identify a reduction, count and compare the number of CH and CO bonds in both the reactant and the product. Try it for the following examples.

Other Important Organic Reactions

In this lesson, you will also encounter the g g following classes of organic reactions: condensation reactions and hydrolysis reactions. reactions Condensation and hydrolysis reactions are both types of substitution reactions. f

Condensation Reactions
In a condensation reaction, two organic molecules combine to form a single organic molecule. A small molecule, usually water, is produced d i ll l l ll t i d d during the reaction. For example, a carboxylic acid and an alcohol can condense to form an ester ester.

Hydrolysis Reactions
In a hydrolysis reaction, water adds to a bond, splitting it in two. This reaction is the reverse of a condensation reaction. reaction For example, water can add to an ester or amide bond. bond A carboxylic acid and an alcohol are produced if an ester bond is hydrolyzed, as shown in the example below. A carboxylic acid and an amine are produced if an amide bond is hydrolyzed.

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