Introduction: Oxidation-reduction reactions in organic chemistry are different from those in general chemistry.

In general chemistry, oxidation refers to the loss of electrons and reduction refers to the gaining of electrons.

Figure 1. Oxidation-Reduction Reaction in General Chemistry (ThinkQuest) The reaction above explains a class oxidation-reduction reaction in general chemistry. In the reaction, the carbon atom in CO2 originally has an oxidation number of +4. However, the same carbon atom has an oxidation number of +2 in the product CO. Thus, the carbon, which gained two electrons and became more negative, was reduced in the reaction. Conversely, hydrogen originally had an oxidation number of 0 in the reactant H2. However, the same hydrogen has an oxidation number of +1 in the product H2O. Thus, the hydrogen, which loses 1 electron and became more positive, was oxidized in the reaction (Bandik). However in organic chemistry, oxidation-reduction reactions are completely different. Oxidation refers to the loss of electron density around a carbon and reduction, conversely, refers to the gaining of electron density around a carbon. Reduction of a carbon can be achieved in several ways in organic chemistry. Three of such ways include: the loss of oxygen from a bond, the addition of hydrogen to a bond, and the replacement of a more electronegative atom (F or O) with a carbon or hydrogen in a bond.

Figure 2. Reduction Reaction in Organic Chemistry (Chem Guide- Blogspot) The reaction above is an example of a reduction reaction in organic chemistry. In this reaction, dimethyl ketone is reduced to 2-propanol with the use of lithium aluminum hydride as the reduction agent. Reduction can be observed in this reaction because a carbon-oxygen double bond is replaced with a carbon-hydrogen bond in the product. This process follows one of the rules stated above, as a more electronegative atom (oxygen) is replaced with hydrogen in a bond with carbon. This reduction of carbon essentially means that there is a gain of electron density around the carbon (Bandik). For reduction to occur in organic chemistry reactions, specific reducing agents need to be used. One of these agents is H2 used in conjunction with a metal like platinum, which acts as a catalyst. This whole process is referred to as catalytic hydrogenation. In addition to the necessity for a catalyst, catalytic hydrogen requires high temperature and pressure. However, the drawback of catalytic hydrogen is that it is not very selective. This process is so reactive will attack every double bond in a compound and replace that bond with a hydrogen atom. An example of a catalytic hydrogen reaction is provided below:

Figure 3. Catalytic Hydrogenation in Organic Chemistry (UC Davis)

In the catalytic hydrogenation reaction above, the ethane molecule is reduce to an ethane molecule. The hydrogen attacked the double bond and replaced it with two hydrogens to form ethane (Bandik). The best reducing agents to use in organic chemistry are nucleophillic hydride delivery agents because they are selective for carbonyl carbons, rather than attacking every double in a compound as seen in catalytic hydrogenation. Some common nucleophillic hydride delivery agents include sodium borohydride (NaB4), lithium aluminum hydride (LiAlH4), diisobutylaluminium hydride (DiBal), and lithium aluminum tri-butoxy hydride (LiAl(tBu)3H. The two most common out of all of these agents are sodium borohydride and lithium aluminum hydride. Although they are both effective reducing agents, they are not the same and are consequently used in different circumstances. Lithium aluminum hydride is more reactive that sodium borohydride due to the fact that aluminum is a much larger atom in comparison to boron. Thus, the aluminum-hydrogen bond is weaker and therefore, will be much easier to break. Additionally, boron is a more electronegative atom than aluminum and will therefore form stronger bonds with hydrogen due to its stronger pull on the hydrogens electrons. In terms of solvents for reactions, sodium borohydride is used in polar protic solvents, while lithium aluminum hydride is used in polar aprotic solvents, such as ethereal solvents. This is due to the fact that if used in protic solvents like alcohols, lithium aluminum hydride will rapidly deprotonate water and alcohols. In fact, this reaction is so violent that the resulting heat could possibly ignite the hydrogen gas that is a product in the reaction. Since sodium borohydride is not as reactive, it is preferred when using protic solvents, like alcohols or water. Both of these reagents reduce aldehydes to primary alcohols and ketones to secondary alcohols. Lithium

aluminum hydride is frequently used to reduce aldehydes, ketones, carboxylic acids, esters, and amides (Bandik). Since sodium borohydride and lithium aluminum hydride are complex compounds, it is a common mistake to think that reduction can be made simpler in organic chemistry with the use of simple ionic compounds like sodium hydride (NaH) and lithium hydride (LiH). However, these ionic compounds are very polar and will not dissolve in polar aprotic solvents like acetone. Additionally, these compounds are so basic that they will deprotonate the polar protic solvent, rather than reduce the organic reagent. Therefore, nucleophillic hydride delivery agents like sodium borohydride and lithium aluminum hydride must be used to accomplish reduction in any organic chemistry reaction (Bandik). In conclusion, oxidation-reduction reactions are different in general chemistry and organic chemistry. In general chemistry, they refer to the addition or loss of electrons, whereas they refer to the addition or loss of electron density around a carbon atom in organic chemistry. Oxidation-reduction reactions organic chemistry also require the use of reducing agents, some of which are H2 combined with a catalyst, sodium borohydride, or lithium aluminum hydride. All of these reagents react differently and the selection of the right reducing agent depends on the conditions of a specific reaction (Bandik).

Works Cited Bandik, George. "Organic Chemistry I." Chevron Hall, Pittsburgh. Lecture. "Catalytic Hydrogenation of Ethene." UC Davis. Web. 16 Nov. 2011. <http://chemwiki.ucdavis.edu/@api/deki/files/2679/=Ethene.jpg>. "Oxidation & Reduction." Web. 16 Nov. 2011. <http://library.thinkquest.org/C006669/data/Chem/electrochemistry/redox.html>. "Reaction with Lithium Aluminum Hydride." Learners' Chemistry. Web. 16 Nov. 2011. <http://chem-guide.blogspot.com/2010/04/preparation-of-monohydric-alcohols.html>.