Chapter 25 The Chemistry of Life: Organic Chemistry Some General Characteristics of Organic Molecules

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1 Chapter 25 The Chemistry of Life: Organic Chemistry general characteristics of organic molecules introduction to hydrocarbons alkanes unsaturated hydrocarbons functional groups: alcohols and ethers compounds with a carbonyl group chirality 25.1 Some General Characteristics of Organic Molecules Organic chemistry is The structures of organic molecules The shapes of organic and biochemical molecules are important in determining their physical and chemical properties. Consider carbon: The stabilities of organic substances The stability of organic substances varies e.g. benzene has special stability due to the delocalization of π electrons. 1

2 Solubility and acid-base properties of organic substances The prevalence of C-C and C-H bonds results in low overall polarity for many organic molecules, and such molecules are soluble in nonpolar solvents Introduction to Hydrocarbons The simplest class of organic molecules is the hydrocarbons 25.3 Alkanes Single bonds only; saturated hydrocarbons (saturated with hydrogen). 2

3 Structures of Alkanes VSEPR theory predicts each C atom is tetrahedral: Structural Isomers In straight-chain hydrocarbons the C atoms are joined in a continuous chain. Branched-chain hydrocarbons are possible for alkanes with four or more C atoms. Structures with different branches can be written for the same formula: Structural isomers are compounds with the same molecular formula but different bonding arrangements. 3

4 Nomenclature of Alkanes Organic compounds are named according to rules established by the International Union for Pure and Applied Chemistry (IUPAC). Names have three parts: prefix base suffix To name a compound 1. Find the longest chain in the molecule: 2. Number the chain from the end nearest the first substituent encountered 4. When two or more substituents are present, list them in alphabetical order. Cycloalkanes Carbon can also form ringed structures. 5- and 6-membered rings are most stable: Reactions of alkanes Rather unreactive due to presence of only C C and C H σ-bonds Unsaturated Hydrocarbons Alkenes Alkenes are unsaturated hydrocarbons that contain C and H atoms and at least one C-C double bond. 4

5 Alkenes are named in the same way as alkanes with the suffix -ene replacing the -ane in alkanes. The location of the double bond is indicated by a prefix Alkenes cannot rotate freely about the double bond (π bond = side-to-side overlap) No rotation means geometric isomers are possible in alkenes Structure affects physical properties of alkenes. Cis and trans do not interconvert. Alkynes Unsaturated hydrocarbons that contain at least one carbon carbon triple bond. Naming is analogous to alkenes Addition Reactions of Alkenes and Alkynes The dominant reactions for alkenes and alkynes are addition reactions: Common additions include H 2 (hydrogenation), H 2 O or hydrogen halides. Alkynes are also capable of addition reactions: 5

6 Mechanism of Addition Reactions A mechanism is an explanation of how a reaction proceeds. Aromatic Hydrocarbons Aromatic structures are formally related to benzene (C 6 H 6 ): Highly unsaturated: very reactive? Even though they contain π bonds, aromatic hydrocarbons undergo substitution reactions more readily than addition reactions. 6

7 25.5 Functional Groups: Alcohols and Ethers Hydrocarbons are relatively unreactive; for an organic molecule to be reactive it needs something additional. Alcohols, R OHR Named from parent hydrocarbon; suffix changed to -ol The O H bond is polar and can participate in hydrogen bonding, so alcohols are more water soluble than alkanes. Ethers, R O R R Compounds in which two hydrocarbons are linked by an oxygen are called ethers. 7

8 25.6 Compounds with a Carbonyl Group The carbonyl group, C=O, plus the type of atoms attached to the carbonyl carbon defines the particular kind of compound. Aldehydes and Ketones Aldehydes must have at least one H atom attached to the carbonyl C Ketones have two carbons bonded to carbonyl carbon Carboxylic Acids Carboxylic acids contain a carbonyl group with an OH attached Esters Esters can be prepared by condensation reactions involving a carboxylic acid and an alcohol; the products are the ester and water Amines and amides Amines are organic bases with general formula R 3 N. 8

9 Amides are composites of carbonyl and amine functionalities 25.7 Chirality in Organic Chemistry Recall that molecules whose mirror images are nonsuperimposable are chiral. Chemists use the labels R and S to distinguish between enantiomers. Many pharmaceuticals are chiral; often only one enantiomer is clinically active. A mixture of two enantiomers in the same quantity is called a racemic mixture. 9

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