Organic Chemistry I Review of Functional Groups I. Functional Groups With Carbon-Carbon Multiple Bonds Alkenes and aromatic compounds contain sp2 hybridized carbon atoms and have pi bonds associated with them. Alkenes contain only double bond. Aromatic compounds can contain both double bonds and triple bonds. Alkynes contain only triple bonds an can be classified as terminal or internal. Enynes are organic molecules that contain both double and triple bonds. Alkenes Alkynes Alkene Diene Triene Arenes (Aromatic Compounds) Enynes N Benzene Pyridine Naphthalene Example drug molecules: O O O O HN OH O O O O Pyrethrin II CH3 Compound found in marigolds Potent Insecticide Dynemicin A Causes skin allegeries in some people Antibacterial and anticancer activity II. Functional Group with Carbon Singly Bonded To An Electronegative Element A. Alkyl Halides: Alkyl halides contain a halogen atom bonded to an sp3 carbon. They may be 1°, 2° or 3° depending on the substitution of the carbon atom bonded to the halogen. Vinyl halides are organic compounds which contain a halogen bonded to the sp2 carbon of an alkene. Aryl halides are organic compounds which contain a halogen bonded to the sp2 carbon of an aromatic system. Alkyl Halides CH H H 3 Cl C H C CH C CH 3 Cl Cl 3 Cl Cl CH 3 CH 3 CH 3 Vinyl halide Aryl Halide 1° 2° 3° 1 Organic Chemistry I Review of Functional Groups B. Alcohols: Alcohols contain an -OH group bonded to an sp3 carbon. Alcohols are designated as primary (1°), secondary (2°) or tertiary (3°) depending on the substitution of the carbon atom to which the hydroxyl group is bonded. secondary alcohol OH C H H H C C OH C C OH H C OH H H C C C HO secondary alcohol primary alcohol teriary alcohol phenol C. Ethers: Ethers are organic compounds which contain an oxygen bonded to two carbon atoms. The carbons may be sp, sp2 or sp3 hybridized. ether Cl CH sp3 3 N O sp2 COC COC CH3 D. Amines: Amines are organic compounds which contain a nitrogen atom bonded to one or more sp3 carbons. Amines may be designated as primary, secondary or tertiary depending on the number of carbon atoms the N atom of the amine is bonded to. tertiary amine N O N C C X Cl N CNH CNH2 CN CN F C C C primary secondary tertiary quarternary salt Flurazepam E. Thiols: Thiols are organic compounds which contain an -SH group bonded to an sp3 carbons. Thiols are related structurally to alcohols. aromatic sp 3 SH sp sp2 CSH CSH CSH 2 Organic Chemistry I Review of Functional Groups F. Sulfides: Sulfides are organic compounds which contain a sulfur atom bonded to two carbon atoms. The carbons may be sp, sp2 or sp3. Sulfides are structurally related to ethers sp3 sp2 CSC CSC . Example Drug Molecules: H CH 3 O S N F 3C ON S CH 3 O HO HO Br N O H Letosteine (Mucolytic) CH 3O O O Oxycodone III. Functional Groups with A Carbon-Oxygen Double Bond A. Aldehydes: Aldehydes contain a carbon oxygen double bond. The carbon atom of the carbonyl group is also bonded to one hydrogen and one carbon atom O O C H C H B. Ketones: Ketones contain a carbon oxygen double bond. The carbon atom of the carbonyl is also bonded to two other carbon atoms. Ketones may be acyclic or cyclic. CH3 OH CH3 O O O Testosterone Acyclic Cyclic ketone 3 Organic Chemistry I Review of Functional Groups C. Carboxylic Acids: Carboxylic acids contain a carbonyl group. The carbon atom of the carbonyl group is bonded to another carbon atom and a hydroxyl group. carboxylic acid O O F OH O O N N HN C OH C OH Ciprofloxacin (antibiotic) D. Esters: contain a carbonyl group. The carbon atom of the carbonyl group is bonded to another carbon atom and an ether type oxygen, i.e., an oxygen bonded to another carbon. Esters are considered to be derivatives of carboxylic acids. Cyclic esters are called lactones. O OCH3 N esters H3C O O O O O CH3 O O O Acyclic esterCyclic ester Acyclic ester Cocaine E. Amides: contain a carbonyl group. The carbon atom of the carbonyl group is bonded to another carbon atom and a nitrogen atom. Amides can be primary secondary or tertiary. The nitrogen atom of the primary amide is bonded to the carbonyl carbon and two hydrogens. The nitrogen atom of a secondary amide is bonded to the carbonyl carbon, one hydrogen and another carbon. The nitrogen atom of a tertiary amide is bonded to the carbonyl carbon and two other carbons. Cyclic amides are called lactams. Amides are derivatives of carboxylic acids. O O HO O O OO O NH N N NH 2 N N H H O Primary Secondary Tertiary Lactam Enalapril (antihypertensive) amide F. Acid Chlorides Acid chlorides are organic compounds which contain a carbonyl group bonded to a chlorine atom. Other halogens may also be bonded to carbonyl groups. These compounds are acid bromides, acid chlorides...Acid chlorides are derivatives of carboxylic acids. O O C Cl C Cl 4 Organic Chemistry I Review of Functional Groups G. Anhydrides Anhydrides are organic compounds which contain two carbonyl groups. The carbonyl groups are separated from each other by an oxygen atom. Anhydrides may be acyclic or cyclic and are derivatives of carboxylic acids. O OO O O O IV. Hetereocycles and Biologically Important Functional Groups Nitrogen Containing Functional Groups &Heterocycles N H N O N N N N O N H H H H Pyrrolidine Pyrazole Pyrrole Imidazole Succinimide H N N O N N H NNH NN N N 2 2 H H Piperidine Pyridine Pyrimidine Pyrazine Piperazine Urea N N CH3NO2 N N N N N H H Quinoline Isoquinoline Indole Purine Nitromethane O NH2 O OH NH2 NH H3C N N NH NNN N O N O N O N N N NH2 N H H H H H Cytosine Uracil Thymine Adenine Guanine (RNA only) (DNA only) Pyrimidine Bases Purine Bases 5.