Chapter 25 Organic and Biological Chemistry

Chemistry, The Central Science, 10th edition Theodore L. Brown; H. Eugene LeMay, Jr.; and Bruce E. Bursten Chapter 25 Organic and Biological Chemistry Organic and Biological Chemistry

Organic Chemistry The chemistry of carbon compounds. Carbon has the ability to form long chains. Without this property, large biomolecules such as proteins, lipids, carbohydrates, and nucleic acids could not form. Organic and Biological

Chemistry Structure of Carbon Compounds There are three hybridization states and geometries found in organic compounds: sp3 Tetrahedral sp2 Trigonal planar sp Linear Organic and Biological

Chemistry Hydrocarbons Four basic types: Alkanes Alkenes Alkynes Aromatic hydrocarbons Organic and Biological

Chemistry Alkanes Only single bonds. Saturated hydrocarbons. Saturated with hydrogens. Organic and Biological Chemistry

Formulas Lewis structures of alkanes look like this. Also called structural formulas. Often not convenient, though Organic and Biological Chemistry Formulas so more often condensed formulas are used.

Organic and Biological Chemistry Properties of Alkanes Only van der Waals force: London force. Boiling point increases with length of chain. Organic and

Biological Chemistry Root Names The roots of basic alkane names are used to name more complex molecules

Organic and Biological Chemistry Structure of Alkanes Carbons in alkanes sp3 hybrids. Tetrahedral geometry. 109.5 bond angles. Organic and Biological

Chemistry Structure of Alkanes Only -bonds in bonds in alkanes Free rotation about CC bonds. Organic and Biological Chemistry

Isomers Have same molecular formulas, but atoms are bonded in different order. Organic and Biological Chemistry

Cycloalkanes Carbon can also form ringed structures. Five-bonds in and six-bonds in membered rings are most stable. Can take on conformation in which angles are very close to tetrahedral angle. Smaller rings are quite strained. Organic and Biological Chemistry

Reactions of Alkanes Rather unreactive due to presence of only CC and CH -bonds in bonds. Therefore, great nonpolar solvents. Organic and Biological Chemistry Alkenes

Contain at least one carboncarbon double bond. Unsaturated. Have fewer than maximum number of hydrogens. Organic and Biological Chemistry Structure of Alkenes Unlike alkanes, alkenes cannot rotate freely about the double bond.

Side-bonds in to-bonds in side overlap makes this impossible without breaking -bonds in bond. Organic and Biological Chemistry Structure of Alkenes This creates geometric isomers, which differ from

each other in the spatial arrangement of groups about the double bond Organic and Biological Chemistry Properties of Alkenes Structure also affects physical properties of

alkenes Organic and Biological Chemistry Reactions of Alkenes Addition Reactions Two atoms (e.g., bromine) add across the double bond. One -bonds in bond and one -bonds in bond are replaced by two

-bonds in bonds; therefore, H is negative. Organic and Biological Chemistry Alkynes Contain at least one carboncarbon triple bond. Carbons in triple bond sp-bonds in hybridized and have linear geometry Also unsaturated

Organic and Biological Chemistry Reactions of Alkynes Undergo many of the same reactions alkenes do. As with alkenes, impetus for reaction is replacement of -bonds in bonds with -bonds in bonds. Organic and

Biological Chemistry Aromatic Hydrocarbons Cyclic hydrocarbons. p-bonds in Orbital on each atom. Molecule is planar. Odd number of electron pairs in -bonds in system. Organic and

Biological Chemistry Reactions of Aromatic Compounds Unlike in alkenes and alkynes, -bonds in electrons do not sit between two atoms Electrons are delocalized; this

stabilizes aromatic compounds Organic and Biological Chemistry Reactions of Aromatic Compounds Due to stabilization, aromatic compounds do not undergo addition reactions; they undergo substitution Hydrogen is replaced by substituent

Organic and Biological Chemistry Structure of Aromatic Compounds Two substituents on a benzene ring could have three possible relationships ortho-: On adjacent carbons. meta-: One carbon between them. para-: On opposite sides of ring.

Organic and Biological Chemistry Reactions of Aromatic Compounds Halogenation Friedel-Crafts Reaction

Reactions of aromatic compounds often require a catalyst. Organic and Biological Chemistry Functional Groups Term used to refer to parts of organic molecules where

reactions tend to occur mass spectroscopy nmr spectroscopy ir spectroscopy Spectroscopy App Organic and Biological Chemistry Organic and Biological

Chemistry Alcohols Contain one or more hydroxyl groups, OH Named from parent hydrocarbon; suffix changed to -ol and number designates carbon to which hydroxyl is attached.

Organic and Biological Chemistry Ethers Tend to be quite unreactive. Therefore, they are good polar solvents. Organic and Biological

Chemistry Carbonyl Compounds Contain Carbon / Oxygen double bond Include many classes of compounds Organic and

Biological Chemistry Aldehydes -bonds in CHO, -bonds in al At least one hydrogen attached to carbonyl carbon Organic and Biological

Chemistry Ketones C-bonds in CO-bonds in C, -bonds in one Two carbons bonded to carbonyl carbon Organic and Biological Chemistry

Carboxylic Acids -bonds in CO2H, -bonds in oic acid Have hydroxyl group bonded to carbonyl group Tart tasting Carboxylic acids are weak acids CH3COOH

Organic and Biological Chemistry Carboxylic Acids Organic and Biological Chemistry Esters

Products of reaction between carboxylic acids and alcohols. Found in many fruits Organic and and perfumes. Biological Chemistry Amides Formed by reaction

of carboxylic acids with amines. Organic and Biological Chemistry Amines Organic bases. Generally have strong, unpleasant odors.

Organic and Biological Chemistry Chirality Carbons with four different groups attached to them are handed, or chiral. Optical isomers or stereoisomers If one stereoisomer is right-bonds in handed, its enantiomer is left-bonds in handed.

Organic and Biological Chemistry Chirality S-ibuprofen Many pharmaceuticals are chiral. Often only one enantiomer is clinically active.

Organic and Biological Chemistry Amino Acids and Proteins Proteins are polymers of -bonds in amino acids. A condensation reaction between the amine end of one amino acid and the

acid end of another produces a peptide bond. Organic and Biological Chemistry Amino Acids and Proteins Hydrogen bonding in peptide chains causes

coils and helices in the chain. Kinking and folding of the coiled chain gives proteins a characteristic shape. Organic and Biological Chemistry Amino Acids and Proteins

Most enzymes are proteins. The shape of the active site complements the shape of the substrate on which the enzyme actshence, the lock-bonds in and-bonds in key model. Organic and Biological Chemistry

Carbohydrates Simple sugars are polyhydroxy aldehydes or ketones. Organic and Biological Chemistry Carbohydrates

In solution they form cyclic structures. These can form chains of sugars that form structural molecules such as starch and cellulose. Organic and Biological Chemistry

Nucleic Acids Two of the building blocks of RNA and DNA are sugars (ribose or deoxyribose) and cyclic bases (adenine, guanine, cytosine, and thymine or uracil). Organic and Biological Chemistry

Nucleic Acids These combine with a phosphate to form a nucleotide. Organic and Biological Chemistry Nucleic Acids

Nucleotides combine to form the familiar double-bonds in helix form of the nucleic acids. Organic and Biological Chemistry

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