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ORGANIC CHEMISTRY Forms of Carbon Carbon has four different allotropes. Allotropes: Forms of the same element with different bonding patterns. 1. Diamond - Carbon is bonded to four other carbon atoms in a tetrahedral pattern 2. Graphite - Carbon atoms are arranged in sheets or layers 3. Amorphous: -Not arranged in any predictable shape - Produced when carbon decomposes 4. Fullerenes - Globe-shaped, cage like arrangements of carbon atoms ORANGIC COMPOUNDS •A compound that is composed of carbon and hydrogen. •It may also contain atoms of other elements, such as oxygen, nitrogen, sulfur, and chlorine. Hydrocarbons: Basic organic compounds contain only carbon and hydrogen. Substituted hydrocarbon: Used when other elements are also present in addition to carbon and hydrogen. Carbon atoms have the unique property of being able to bond to each other and form long "chains" of carbons, or to form circular "rings" of carbons. The addition of one atom of a different element makes an entirely new compound is the reason that there are millions of organic compounds in the world. The simplest hydrocarbon is methane, which is made of one carbon atom surrounded by four hydrogen atoms. Aliphatic Hydrocarbons Aliphatic hydrocarbons: The simplest hydrocarbons are those whose carbons are joined in line one to another. Alkanes 1. First group 2. Name of each of these compounds ends in "-ane" 3. They have the generic formula of CnH2n+2 4. They have a single covalent bond between them Also called saturated hydrocarbons, which means that all of the carbons have the maximum number of bonds (4). The first ten alkanes should be memorized, because their names are the basis for most of the naming of the rest of the organic compounds. 1. CH4 : methane 2. C2H6: ethane 3. C3H8: propane 4. C4H10: butane 5. C5H12: pentane 6. C6H14: hexane 7. C7H16: heptane 8. C8H18: octane 9. C9H20: nonane 10. C10H22: decane Aliphatic Nomenclature ALKANES ALKANE NOMENCLATURE 1. Determine the longest continuous chain of carbon. (Parent chain) 2. Number carbons in parent chain. Do this by starting at the end that gives the attached groups the smallest number. 3. Add numbers to the names of the attached groups to identify their position. Numbers become prefixes to the name of the parent. 4. Use prefixes to indicate if more than one of the same attached group is present. 5. List attached groups in alphabetical order. Ignore prefixes. 6. Use commas to separate the numbers, hyphens to separate the numbers & words. The name of the alkane is written as one word. Common Alkyl Groups 1. Methyl 2. Ethyl 3. n-propyl CH3 CH2CH3 CH2CH2CH3 Common Alkyl Groups 4. n-Butyl CH2CH2CH2CH3 5. Isopropyl CH3CHCH3 Common Alkyl Groups 6. t-Butyl CH3 C CH3 CH3 Common Alkyl Groups 7. Amino NH2 8. Nitro NO2 9. Bromo Br Common Alkyl Groups 10. sec-Butyl H CH3 C CH2 CH3 Examples CH3 A. CH3 C CH2 CH3 H 2-methylbutane B. NO2 Br CH3 CH CH CH3 2-bromo-3-nitrobutane C. 2,2,4-trimethylhexane CH3 CH3 CH3 C CH3 CH2 CH CH2 CH3 ALKENES 1. Next group of hydrocarbons 2. The carbon chain has a double covalent bond 3. They have the generic formula CnH2n 4. The names end in "-ene" 5. They represent the simplest of the unsaturated hydrocarbons. 6. An alkene has two less hydrogens than an alkane. ALKENE NOMENCLATURE 1. Find the longest chain with the double bond. 2. Number the chain so the double bond gets the lowest number. 3. Name & number attached groups as you would for alkanes. 4. Parent gets –ene ending; Indicate position of double bond with a number. ALKENE NOMENCLATURE Examples A. CH2 CH CH2 1-butene CH3 ALKENE NOMENCLATURE B. CH CH3 CH CH3 2-butene ALKENE NOMENCLATURE 1,3-butadiene C. H C H H C C C H H H ALKENE NOMENCLATURE D. propadiene CH2 C CH2 ALKYNES 1. They have a triple covalent bond in the carbon chain 2. They have the generic formula CnH2n-2 3. They have two less hydrogens than alkenes Alkyne Nomenclature 1. Find the longest chain with the triple bond & number it so the triple bond has the lowest number. 2. Name and number the attached groups. 3. Parent gets –yne ending; Indicate position of triple bond with a number. Alkyne Nomenclature Examples: A. CH C CH2 CH3 1-butyne Alkyne Nomenclature B. 3,3-dimethyl-1-butyne CH3 CH C C CH3 CH3 Cyclo-Compounds 1. Sometimes the chains can be circled and the end carbons join together. 2. This brings about the loss of two hydrogen atoms 3. An example is that of the six-carbon hexane forming the six-carbon cyclohexane which has the formula C6H12 4. You use of the prefix "cyclo-" in front of the parent name, hexane EXAMPLES EXAMPLES AROMATICS 1. The other main group of hydrocarbons is that of the aromatic hydrocarbons 2. They contain six carbons arranged in a "ring" and contain three double covalent bonds between every other carbon-carbon pair. 3. The basic aromatic hydrocarbon is benzene, C6H6 4. Ways to represent benzene Aromatics Nomenclature 1. Monosubstituted name like other hydrocarbons with –benzene as the parent name. 2. Disubstituted named using prefixes ortho (1,2) meta (1,3) para (1,4) Aromatics Nomenclature Br A. Br ortho 1,2-dibromobenzene Aromatics Nomenclature o-dibromobenzene B. Br para 1,4-dibromobenzene Br Aromatics Nomenclature p-dibromobenzene C. Br meta 1,3-dibromobenzene Br Aromatics Nomenclature m-dibromobenzene D. CH3 3-ethyl-1-methylbenzene CH2 CH3 Substituted Hydrocarbons 1. Atoms of other elements can be joined to the carbons in place of one or more hydrogens. 2. Oxygen, nitrogen, sulfur and the halogens are the most common atoms that replace hydrogens. 3. The resulting compound is called a substituted hydrocarbon. 4. Sometimes a combination of two of these other elements will be found in place of hydrogens. 5. These other elements give rise to what are called functional groups. ALCOHOLS 1. The most common of the functional groups 2. Contains an "- OH" group, which is known as the hydroxyl group 3. An aliphatic hydrocarbon that has one hydroxyl group attached to a carbon is called an alcohol. Alcohol Nomenclature 1. Select the longest carbon chain containing –OH group. 2. Replace the -e ending of the parent alkane with -ol 3. Number the alkane chain beginning at the end nearer the –OH group. 4. Number the attached groups according to their position Alcohol Nomenclature 2-methyl-2-propanol A. CH3 CH3 C CH3 OH Alcohol Nomenclature B. CH3CH2OH Alcohol Nomenclature ethanol C. CH3OH methanol Alcohol Nomenclature D. H H H 2-butanol H H C C C H H OH H C H ETHERS 1. Results when there is an oxygen atom between two carbons in the chain 2. Ethers are represented as R-O-R', where R and R' can be the same or different hydrocarbon units. Ether Nomenclature 1. Identify the two attached groups and add the word ether. 2. If there are more than 2 attached groups name as a benzene ring. Ether Nomenclature A. CH3CH2 O CH3 Ethylmethyl ether Ether Nomenclature Diethyl ether B. CH3CH2 O CH2CH3 Aldehydes Aldehydes • These compounds show the arises when an oxygen atom is 1. A new class of substituted hydrocarbons generic formula, double bonded to the carbon at the end of the chain. 2. These compounds show the generic formula, O R C H Aldehyde Nomenclature 1. Replace the – e of the parent alkane with –al 2. The longest chain selected includes the aldehyde group. 3. The carbon in the aldehyde group is always numbered as the #1 carbon. Aldehyde Nomenclature A. O H C H Aldehyde Nomenclature Methanal B. O CH3 C H Ethanal Ketones Ketones •The•generic formula for ketones A different class of organic compounds results if the C=O occurs somewhere along the chain other than on the end carbon is •The generic formula for ketones is O R C R Ketone Nomenclature 1. Replace the – e of the parent alkane with – one 2. The longest chain selected includes the ketone group. 3. Numbering begins nearer the carbonyl carbon. Ketone Nomenclature A. O CH3 C CH3 Ketone Nomenclature propanone B. O C CH3 Carboxylic Acids 2-butanone CH2CH3 d a lot in nature formed by xidation of alcohols and Carboxylic Acids •Found a lot in nature formed by the oxidation of alcohols and aldehydes. ydes. • These compounds show the generic formula, compounds show the c formula, O R C OH Carboxylic Acid Nomenclature 1. Carboxyl carbon is number one. 2. Parent alkane – e is replaced with – oic acid Carboxylic Acid Nomenclature Propanoic Acid A. O CH3 CH2 C OH Carboxylic Acid Nomenclature B. 5-methylhexanoic acid CH3 O CH3CCHCH2CH2COH Polymers 1. Large molecule formed by the covalent bonding of repeating smaller molecules. 2. Monomer: Smaller molecules that combine to form the repeating unit of a polymer. 3. Polymerization: Joining two or more monomers together creating a polymer. 4. First synthetic polymer was nylon (1930s). 5. Two methods synthesizing polymers are addition and condensation polymerization. 6. Addition: Unites thousands of monomers into a single enormous molecule 7. Condensation: Joining of two molecules (monomers) and the elimination of a small molecule, usually water.