NRAN80323_ORGANICchemistry_FALL23.pptx

ORGANIC CHEMISTRY Gregory Collins, DNP, CRNA PHYSICAL SCIENCE IN NURSE ANESTHESIA NRAN 80323 1 ORGANIC CHEMISTRY READING: Nagelhout / Chapter 15 / 201-204 Shubert / Chapter 11 / 319350 OBJECTIVES: CARBON BONDING HYDROCARBON GROUPS ALCOHOLS ETHERS AMINES CARBONYL GROUPS Carbohydrates Esters Amide...

ORGANIC CHEMISTRY Gregory Collins, DNP, CRNA PHYSICAL SCIENCE IN NURSE ANESTHESIA NRAN 80323 1 ORGANIC CHEMISTRY READING: Nagelhout / Chapter 15 / 201-204 Shubert / Chapter 11 / 319350 OBJECTIVES: CARBON BONDING HYDROCARBON GROUPS ALCOHOLS ETHERS AMINES CARBONYL GROUPS Carbohydrates Esters Amides 2 CARBON Basis for all life • Form stable COVALENT bonds to other carbon atoms • Can form single, double, and triple bonds • Long carbon chains can be produced • • Will bond with many other elements • Large number of chemicals are possible • Most drugs are organic compounds with CARBON skeleton • CARBON skeleton can be linear, branched, cyclic • Contribute to overall shape of drug molecule 3 FUNCTIONAL GROUPS • ORGANIC molecule = CARBON backbone + FUNCTIONAL GROUP(S) • Non-carbon atoms are typically considered FUNCTIONAL GROUPS • FUNCTIONAL GROUPS are sets of atoms bonded in a particular fashion • FUNCTIONAL GROUPS largely define the chemical and physical properties of the compound 4 BONDING BOND LENGTH • Distances between two bonded atoms • single bonds > double bonds > triple bonds BOND STRENGTH • Based on energy necessary to break a chemical bond • triple bonds > double bonds > single bonds COVALENT BONDS • SHARED pair of electrons between 2 atoms • Electrons can originate from one atom or 1 electron from each atom • Can be thought of an an OVERLAP of ORBITALS surrounding the atomic nuclei • Atomic structure of an individual atom determines 5 CLASSIFYING Assigned by the FUNCTIONAL COMPOUNDS GROUP that is attached to the carbon or carbon chains FUNCTIONAL GROUPS: Hydrocarbons C & H only Alcohols R – OH Ethers R – O – R’ Amines R – NH2 Ketones R – (C=O) – R’ Aldehydes R – (C=O) – H Carboxylic Acids R – (C=O) – 6 HYDROCARBONS Contain only CARBON and HYDROGEN HYDROCARBON FUNCTIONAL GROUPS: ALKANES, ALKENES, ALKYNES, AROMATICS 7 ALIPHATIC Hydrocarbon compounds that COMPOUNDS DO NOT incorporate any AROMATIC RINGS in their molecular structure ALIPHA TIC Alkanes Alkenes Alkynes NONALIPHATIC Aromatics 8 ALKANES Also known as PARAFFINS SIMPLEST of the organic compounds Form structure or SKELETON for other functional groups Characterized by C-C SINGLE BONDS Provide an ideal starting point for studying and naming organic compounds PHYSICAL PROPERTIES: • Non-polar molecules • Not soluble in water Increase as # of C • Low density increase • Low melting point • Low boiling point METHANE ETHANE 9 ALKANES NAMING ALKANES USING I.U.P.A.C. RULES International Union for Pure and Applied Chemistry 1. Name the longest chain as the parent (The longest chain, not the longest horizontal chain!) 2. Name substituents (alkyl groups or halogens) in alphabetical order 3. Use multipliers to indicate the number of identical substituents with di = 2, tri = 3, tetra = 4, penta = 5, etc.) 4. Number the parent chain (begin at one end, not in the middle), and indicate substituent position with lowest possible numbers (numbers are called locants) 10 ALKANES ALKYL GROUPS: • ALKANE with HYDROGEN atom removed • Always connected to molecular “parent”, cannot exist alone • Sometimes represented by “R-” in chemical formula • Named by replacing “-ane” with “-yl” CYCLOALKANES: • Chain of carbon atoms (C-C SINGLE BOND) forms a RING STRUCTURE • Single bonds differentiate CYCLOALKANES from CYCLOPROPANE 11 ALKENES Also known as OLEFINS Characterized by at least one C=C DOUBLE BOND ETHENE Follow IUPAC naming rules, replace “-ane” with “-ene” HYDROGENATION: • Introduction of H, bonds in place of C=C DOUBLE BOND, produces ALKANE • Changes in physical characteristics; vegetable oil to vegetable shortening ETHENE ETHANE POLYMERIZATION: • Strength of C=C DOUBLE BOND used to form long, stable chains • 12 ALKYNES Characterized by at least one C C TRIPLE BOND Follow IUPAC naming rules, replace “ane” with “-yne” Rare in pharmacology applications 13 CIS/TRANS ISOMERISM GEOMETRIC ISOMERISM EXIST WHEN TWO OR MORE STRUCTURAL ARRANGEMENTS ARE POSSIBLE DUE TO THE TYPE OF BOND ALKANES - can rotate about all bonds, no geometric isomers ALKENES - rigid bond, can have geometric isomers ALKYNES - rigid bond but linear, no geometric isomers TRA CIS 14 AROMATICS Sometimes called ARENES Functional group is BENZENE RING BENZENE Characterized by 3 C-C single bonds and 3 C=C double bonds Bonds are not alternating, but DELOCALIZED, allowing entire molecule to share strength of double bond Very stable arrangement, frequent use in pharmacology Use “BENZENE” in naming skeleton Called a PHENYL group when added to another compound KETAMINE PROPOFOL MIDAZOLAM 15 ORGANOHALOGENS Organic compounds that contain one or more HALOGEN atoms If parent compound is alkane, also known as AKYL HALIDES and HALOALKANES If parent compound is benzene, also known as ARYL HALIDES Common in anesthetic agents CHLOROFOR M HALOTHANE BROMOBENZ ENE 16 FUNCTIONAL GROUPS BASED ON WATER Replacing ONE hydrogen atom on water with an organic group affords an ALCOHOL (R-O-H) Replacing BOTH hydrogen atoms on water with organic 17 ALCOHOLS Replacing one HYDROGEN atom on water molecule with an ALKYL GROUP produces ALCOHOL HYDROXYL GROUP (-OH) is functional group Generic formula is R – OH METHANOL Water soluble, larger R groups decrease solubility, additional –OH groups increase solubility Named using IUPAC rules, adding “-ol” suffix Aromatic alcohols are called PHENOLS 2,6 – diisopropylphenol PROPOFOL 18 ETHERS Replacing BOTH of the HYDROGEN atoms with ALKYL GROUPS or CARBON CHAINS produces an ETHER Creates OXYGEN BRIDGE functional group DIETHYL ETHER Generic formula is R – O – R’ Relatively INERT, do not react with oxidizing or reducing agents Common compound in INHALED VOLATILE ANESTHETICS ISOFLURANE PHYSICAL PROPERTIES: • Less polar than alcohols • Lower boiling temperature than alcohols • Not soluble in water DESFLURANE • Chemically inert SEVOFLURANE 19 AMINES Functional groups derived from AMMONIA (NH3) NITROGEN is very electronegative, results in N-H bond being very polar, high boiling points Organic BASES with substituted AMMONIA Can form hydrogen bonds, SOLUBLE in water Many biologically significant amines: amino acids, nucleic acids (DNA/RNA), catecholamines AMINOSTEROID General formulas: • Primary amine R – NH2 • Secondary amine R2 – NH • Tertiary amine R3 – N • Quaternary amine R4 – N+ NON-DEPOLARIZING MUSCLE RELAXANT ROCURONIUM 20 CARBONYL GROUPS Based on carbon DOUBLE BONDED to OXYGEN (C=O) STRONG bond, common occurrence in chemistry CARBONYL GROUP CARBONYL-BASED Functional Groups: ALDEHYDE Aldehydes (-H) KETONE Ketones (-R) CARBOXYLIC ACID Carboxylic Acids (-OH) ESTER Esters (-OR) AMIDE 21 CARBONYL GROUPS ALDEHYDES: • ALKYL group and HYDROGEN atom bonded to CARBONYL GROUP • Easily oxidized to carboxylic acid • Common factors on biochemistry KETONES: • TWO ALKYL groups bonded to CARBONYL GROUP • Abundant in nature, biology, pharmacology CARBOXYLIC ACID: • CARBOXYL GROUP (CARBONYL group + HYDROXYL group) • Negatively charged at physiologic pH (CARBOXYLATE ANIONS) 22 CARBONYL GROUPS ESTERS: • Condensation products between CARBOXYLIC ACIDS and ALCOHOLS • Metabolized by opposite reaction of HYDROLYSIS (faster than amides) • Often used as PRO-DRUG, lipophilic and masked H groups • HYDROLYSIS produces carboxylic acid (active drug) and alcohol • Biologically bonds fatty acids to glycerin to form triglycerides AMIDES: • Condensation products between CARBOXYLIC ACIDS and AMINES • Amides create PEPTIDE BONDS, bonding AMINO ACIDS together to form PROTEINS PROCAINE LIDOCAINE 23 SUMMARY UNDERSTANDING: Describe carbon chains in terms of bonds and shapes. Describe the composition and importance of functional groups. How does carbon bonding contribute to bond length & strength? List the 4 basic hydrocarbon groups. Define & differentiate alkanes from other hydrocarbons. Define & differentiate alkenes from other hydrocarbons. Define & differentiate alkynes from other hydrocarbons. Define & differentiate aromatics from other hydrocarbons. What is geometric isomerism; which hydrocarbon is affected and why? Differentiate CIS from TRANS configuration. Describe the relationship between halogens and hydrocarbons. Define and describe alcohols in terms of structure, properties, and reactivity. Define and describe ethers in terms of structure, properties, and reactivity. Define and describe amines in terms of structure, properties, and reactivity. What are the common characteristics among the members of the carbonyl group? What are the differences among the members of the carbonyl group? MASTERY: Hydrocarbons C Alcohols R Ethers R Amines R Ketones R Aldehydes H Carboxylic Acids OH Esters R Amides R & H only – OH – O – R’ – NH2 – (C=O) – R’ R – (C=O) – R – (C=O) – – (C=O) – OR’ – (C=O) – NH2 24