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Organic Chemistry

Organic Chemistry

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Organic Chemistry The organic chemistry supplement provides an overview of the field of organic chemistry.

Many majors require an entire year of the so-called "O-Chem", so don't think that this is a comprehensive treatment of organic. The focus of the supplement is on two broad topics: hydrocarbons and functional group classes. In addition, there is a description of the meaning of chemical formulas of different types. Organic chemistry is the chemistry of carbon compounds. The name arises from the association of these compounds with living organisms. In fact, it was thought for a long time that organic compounds could only be obtained from living organisms and that it wasn't possible to synthesize organic compounds (the vital force theory.) This theory was disproved in 1828 when the German chemist Friedrich Wöhler synthesized urea, an organic compound which is a component of urine, from the inorganic salt ammonium cyanate. [Although ammonium cyanate contains carbon, it is not considered to be an organic compound; other examples of this are carbonic acid (H2CO3), the carbonate ion (CO3)2- , the cyanide ion (CN)- , and a few others.] There are countless organic compounds of all sorts. One of the reasons for this vast number is that carbon can form bonds to itself, making very large chains and rings possible. In addition, carbon forms stable bonds to hydrogen, oxygen, nitrogen, sulfur and the halogens, as well as other atoms. In all organic compounds, however, there is one rule which is not violated: carbon always forms four bonds. We will consider the following types of organic compounds: I. Hydrocarbons Hydrocarbons are compounds of only two elements: carbon and hydrogen. There are many subclasses of hydrocarbons, but we'll consider only the following: A. Aliphatic Hydrocarbons - these are compounds in which the bonding electrons are localized between two atoms. In other words, the electrons in the bonds of the molecule don't have the freedom to roam around the molecule. 1. Non-cyclic aliphatic hydrocarbons a. Alkanes - these compounds all have the general formula CnH2n+2, where n is a number from 1 to infinity (in a practical sense, the upper limit for n is on the order of several hundred thousand.) The simplest alkane is methane, CH4. The alkane with two carbons is ethane, C2H6. All alkanes with two or more carbon atoms contain carbon-carbon single bonds. The geometry around an alkane carbon is tetrahedral; picture it as a camera tripod, with the carbon at the head of the tripod and the four atoms bonded to the carbon at the end of the four "legs." The bond angle around a tetrahedral carbon is 109°28´, or about 109.5°. You should know the names of the first ten alkanes, from methane to decane. Another reason for a huge number of organic compounds is compounds with the same formula can have a different arrangement of atoms, making them different compounds with different chemical and physical properties. Compounds with the same formula but a different arrangement of atoms are known as isomers. Don't confuse this term with isotopes, which are related nuclei. Hydrocarbons which are bonded such that the carbon atoms are arranged in a continuous fashion, with no branching, are known as straight-chain hydrocarbons. Pentane, C5H12 (notice that this alkane follows the general formula above) is an example of a straight-chain alkane. The "line" formula for this compound is CH3CH2CH2CH2CH3. A common abbreviation for this is the formula C-C-C-C-C. Notice that the hydrogens aren't shown, but that the number of hydrogens on each carbon can be deduced by remembering that carbon always forms four bonds. An isomer of pentane is 2-methylbutane, whose formula can be written as CH3CH(CH3)CH2CH3. Notice that the methyl (CH3) group in the middle is bonded to the second carbon atom from the left; it "branches" from the continuous chain made by the first, second, fourth, and fifth carbons (from left to right in the formula above). Thus, it is known as a branched-chain hydrocarbon. Alkanes are named by identifying the longest continuous chain of carbon atoms, and using this as the base name (eight continuous carbons would give a base name of octane), then naming the substituents on the chain and identifying their position with the number of the carbon to which they are bonded. Here's an example: the compound whose formula can be written CH3CH2C(CH3)(C2 H5)CH2CH2CH(CH3) CH2CH3 is 3-ethyl-3,6-dimethyloctane. Notice that it is an isomer of the straightchain compound with twelve carbons (C12H26, or dodecane.) b. Alkenes - this class of hydrocarbons contain a carbon-carbon double bond. Each carbon of the double bond is attached to three other things: another carbon and two other atoms or groups of atoms, resulting in a planar carbon atom with 120° bond angles around the carbons of the double bond. The other carbon atoms in the alkene are like alkane carbons: each carbon bonded to four other atoms or groups (methyl, ethyl, etc.) Since carbon can only form four bonds, the formation of a double bond requires the elimination of two hydrogens (one from each carbon involved in the double bond.) Thus, the general formula for an alkene is CnH2n. The simplest alkene is the one with two carbons: ethene, whose formula is C2H4. (Recall that the corresponding alkane, ethane, has a formula of C2H6). In addition to the isomers which arise from branching, as in the alkanes, alkenes can form another type of isomers known as cis/trans isomers. The cis isomer has similar groups on the same "side" of the double bond, while the groups in the trans isomer are on opposite sides of the double bond. c. Alkynes - this class of hydrocarbons contains a carbon-carbon triple bond. Each carbon involved in the triple bond is bonded to only one other atom or group. The bond angle around each carbon is 180°, resulting in a linear geometry. The other carbon atoms in the alkene are like alkane carbons: each carbon bonded to four other atoms or groups (methyl, ethyl, etc.) The general formula for an alkyne is CnH2n-2. The simplest alkyne is ethyne, C2H2 (common name: acetylene.) 2. Cyclic aliphatic hydrocarbons - if a chain of carbon atoms eliminated two hydrogens by bonding end-to-end, a cyclic structure is formed. The simplest cyclic hydrocarbon is the three-carbon ring cyclopropane. The three carbons in the ring are at the vertices of a triangle; in fact, a triangle is the common symbol for cyclopropane. Other regular polygons represent larger rings: a square for cyclobutane, a pentagon for cyclopentane, and hexagon for cyclohexane, etc. The hydrogens aren't usually shown, but remember that since each carbon can form four bonds, and there are already two other carbons bonded to a particular carbon, each carbon in a cyclic aliphatic hydrocarbon involving only single bonds is bonded to two hydrogens. Thus, the formula for cyclopropane is C3H6; cyclobutane is C4H8. Notice that this is the same as the general formula for an alkene, although there are no double bonds. This is because the linking of the two ends of a carbon chain results in the loss of two hydrogen atoms. Cyclic hydrocarbons can also contain double bonds, although each double bond will result in two fewer hydrogens in the molecule. For example, cyclohexane has the formula C6H12, while cyclohexene has the formula C6H10. Aromatic hydrocarbons - these compounds, unlike aliphatic hydrocarbons, have delocalized electrons; i.e., electrons which are free to move throughout the entire molecule. The prototype of this class of compounds is benzene , C6H6. This is a cyclic molecule, like cyclohexane, but there

B.

while the bonds in benzene are intermediate between single and double bonds.) The two R groups in the general formula may be the same or they may differ.tertiary (3°) alcohols are those in which the carbon bonded to the OH is bonded to three other carbons. The simplest ether is dimethyl ether. An ester is formed by the reaction between a carboxylic acid and an alcohol. formally representing three double bonds) which can move freely in a circular area above and below the plane of the molecule. has different properties than an alcohol. i. . also known as isopropanol or 2hydroxypropane: CH3CH(OH)CH3. In other words. [Note: one or two of the R groups may be hydrogen. Don't confuse this class with ethers. CH3COCH3. the alcohol is classified as a primary (1°) alcohol. except that instead of two hydrogen atoms there are two organic groups.. which can be represented as n RCOOH + M(OH)n ----> (RCOO)nM + n H2O. Ketones can also be named as a derivative of the parent hydrocarbon. You will be responsible for recognizing the following classes of functional group derivatives: [Note: the "R" in the general formula represents an alkyl (aliphatic) or aryl (aromatic) group.II. with all 12 atoms in the plane. If the carbon bonded to the OH is bonded to two other carbons. A common example of a secondary alcohol is isopropyl alcohol. is diethyl ether. An unsymmetrical ketone would be something like isopropyl phenyl ketone. The OH. and the best way to view it is that it is a planar molecule. where M represents some metal. The formation of hydronium ion is what makes the substance an acid.it is bonded to the carbon. Aldehyde: General formula = RCHO. however. As you might expect. Aldehydes can be considered to be a ketone where one of the R groups is a hydrogen. An example of this is methylamine. the general reaction iscarboxylic acid + alcohol -----> ester + water. R2NH. which is also doubly-bonded to the carbonyl oxygen. 2) all bonds in cyclohexane are single bonds. no hydrogens) we have a tertiary (3°) amine. C2H5OC2H5. CH4.these compounds contain certain groupings of atoms (called functional groups because they determine the function. The other product of this ionization is called a carboxylate ion. Keep in mind. however. using -one as a suffix and specifying the number of the carbon with the double bond to the carbonyl oxygen. the compound is referred to as a primary (1°) amine. One of the most common ethers. e. an inorganic compound. (CH3)3N. that the hydrogen is not bonded to the oxygen in an aldehyde .g. The formula is HCHO. B. D.. Amine: General formula = NR3. The best way to draw benzene is as a hexagon with a circle inside (the circle indicates that some of the electrons in the molecule are delocalized). Because the carbon bonded to the carbonyl oxygen is also bonded to the hydrogen. In other words. Functional group derivatives of hydrocarbons . G. An amide is the product of a condensation reaction between a primary or secondary amine and a carboxylic acid. CH3OC2H5. Finally. where the two R groups are the same. This is a result of the electron-withdrawing effect of the carbonyl (C=O) group. E. although they are allowed to be the same. and that there are six electrons (three pairs. if there are three R groups (and. a doubly-bonded oxygen. CH3OH. If the carbon bonded to the OH group is bonded to only one other carbon. usually a Group IA or IIA metal ion. The common name of this extremely common solvent (used as nail polish remover) is acetone. then it is classified as a secondary (2°) amine.e. and the name of the ester is methyl acetate (or methyl ethanoate). ethylmethylamine. often written as C2H3O2-. where R = H.e. they are structurally like water. The simplest carboxylic acid is formic acid. there is a lone pair of electrons on the nitrogen atom. we get methyl alcohol. there are no real double bonds in the molecule. if the formula is RNH2. CH3CH2CH2OH. where the italicized 't' refers to tertiary. do not think that the double bonds in this structure can "move" around the ring. Formaldehyde is used as embalming fluid. the formula is HCOOH. the solute in vinegar: CH3COOH. For example.] A. this means that the aldehyde functional group will always be at the end of a multicarbon chain. etc. An example of this is grain alcohol. Ester: General formula = RCOOR´. If all three are H. the preferred name for the dimethyl ketone example above is 2-propanone. If we substitute this group for one of the hydrogen atoms in methane. (CH3)2CHCOC6H5. C. are some important differences: 1) there are twice the number of hydrogens in cyclohexane as in benzene. Notice that the hydrogen on the amine combines with the OH on the acid to split off the water molecule. For example. the functional group which defines an alcohol is the -OH group (the line in front of the oxygen atom indicates that the group is attached to a carbon atom of a hydrocarbon). The simplest aldehyde is formaldehyde (also called methanal). CH3OCH3. or properties. and an OH group. the alcohol is secondary (2°). CH3NH2. Amide: General formula = RCONR2. To see four visual models for the structure of EDTA. The compound with the formula CH3COOCH3 is formed by the reaction between acetic acid (also called ethanoic acid) and methyl alcohol (make sure you understand why these are the reactants).+ H3O+. as pointed out above. It is common to draw the structure of benzene as a hexagon with alternating single and double bonds. III. This compound can also be named 2-hydroxy-2-methylpropane: CH3C(OH)(CH3)CH3. An example of an unsymmetrical ether is ethyl methyl ether. an extremely flammable solvent. where R = H. Three-dimensional structures can be represented in many ways. The carboxylate anion of acetic acid is the acetate ion. Note that there are three groups bonded to the carbon: R. however. but this is not an accurate picture of the bonding in benzene. in fact. Often this group of compounds is called carboxylic acids instead of simply acids. Notice that the second carbon from the left is not bonded to any hydrogens. in that it loses a hydrogen ion relatively easily. As an example of an ester where the groups are different. ROH. Note that the functional group is written this way to differentiate it from an alcohol. but this formula does not give useful visual information about the actual 3-dimensional geometry of the molecule. of the molecule) which can be viewed as replacing a hydrogen atom of an alkane. Note that this compound is an isomer of the primary alcohol n-propanol. If the nitrogen is bonded to two R groups. and the name is ethyl benzoate. Remember that in all amines. An example of this situation is trimethylamine. One of the characteristic reactions of an acid is neutralization with a base. Examples of this would be dimethylamine. This type of reaction is called a condensation reaction: one where two molecules combine to form a larger molecule by splitting off a small molecule (in this case. The next acid in the series is the extremely common acid acetic acid (ethanoic acid).) Representation of Formulas The "line formula" for ethylenediaminetetraacetic acid (EDTA) is (HOOCCH2)2NCH2CH2N(CH2COOH)2. The aldehyde where R = methyl is acetaldehyde (or ethanal). F.] If the nitrogen is bonded to only one R group. Acid: General formula = RCOOH. that leaves only one more bond available to it. The general ionization reaction is represented by RCOOH + H2O -----> RCOO. CH3CHO. An example is t-butyl alcohol. In particular. water. The amide functional group is very important biologically: all proteins are polymers made up of a large number of amide linkages (biochemists call the amide linkages in proteins peptide linkages. Alcohol: General formula = ROH. Ether: General formula = ROR´ [the prime on the second R group implies that the two R groups do not necessarily have to be the same. whereas the carbonyl group in a ketone can be anywhere in the middle of a long chain. RCOOH + R2NH -----> RCONR2 + H2O.] Ethers are simply two R groups separately bonded to the same oxygen. An example of a symmetrical ketone is dimethyl ketone. the compound is NH3 (ammonia). or ethyl alcohol: CH3CH2OH. H. i. Ketone: General formula = RCOR´. Ketones are compounds where a carbonyl group (C=O) is bonded to two organic groups. CH3COO-. These two examples represent symmetrical ethers. as a consequence. The formula of the product is C6 H5COOC2H5. consider the ester formed between benzoic acid (C6H5COOH) and ethyl alcohol (C2H5OH).

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