Chemistry 121(01) Winter 2009 Introduction to Organic Chemistry and - PDF document

Chemistry 121(01) Winter 2009 Introduction to Organic Chemistry and Biochemistry Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@chem.latech.edu Office: 311 Carson Taylor Hall ; Phone: 318-257-4941; Chapter 14: Alcohols, Phenols and Ethers Chapter 14: Alcohols, Phenols and Ethers Office Hours: MTW 9:00 am - 11:00 am; TR 9::00 - !0:00 am & 1:00-2:00 pm. December 19, Test 1 (Chapters 12-14) Sections 14.1- Sections 14.1 -4.21 4.21 January 2 Test 1 (Chapters 15-16) February 6 (Chapters 17-19) February 27, (Chapters 20-22) March 2, 2009, Make Up Exam: Bring Scantron Sheet 882-E Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-1 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-2 Chapter 14: Alcohols, Phenols, and Ethers Alcohols, Phenols, and Ethers Chapter 5. Alcohols, Phenols, and Ethers Chapter 14: Chapter 5. Alcohols, Phenols, and Ethers 14.1 Bonding Characteristics of Oxygen Atoms in Organic Compound 14.1 Bonding Characteristics of Oxygen Atoms in Organic Compounds s 14.2 Structural Characteristics of Alcohols 14.2 Structural Characteristics of Alcohols Functional groups: Functional groups: 14.3 Nomenclature for Alcohols 14.3 Nomenclature for Alcohols 14.4 Isomerism for Alcohols 14.4 Isomerism for Alcohols alcohol: R- alcohol: R -O O- -H H 14.6 Physical Properties of Alcohols 14.6 Physical Properties of Alcohols phenols: phenols: Ar Ar- -OH OH 14.7 Preparation of Alcohols 14.7 Preparation of Alcohols 14.8 Classification of Alcohols 14.8 Classification of Alcohols ether: R- -O O- -R' R' ether: R 14.9 Chemical Reactions of Alcohols 14.9 Chemical Reactions of Alcohols thiol thiol: R : R- -S S- -H H 14.11 Structural Characteristics of Phenols 14.11 Structural Characteristics of Phenols 14.12 Nomenclature for Phenols 14.12 Nomenclature for Phenols 14.13 Physical and Chemical Properties of Phenols 14.13 Physical and Chemical Properties of Phenols Phenyl, Ar = C 6 H 5 Alkyl, R = CH 3 Mehtyl etc. 14.15 Structural Characteristics of Ethers 14.15 Structural Characteristics of Ethers 14.16 Nomenclature for Ethers 14.16 Nomenclature for Ethers 14.18 Physical and Chemical Properties of Ethers 14.18 Physical and Chemical Properties of Ethers 14.20 Sulfur Analogs and Alcohols 14.20 Sulfur Analogs and Alcohols 14.21 Sulfur Analogs of Ethers 14.21 Sulfur Analogs of Ethers Menthol: A Useful Naturally Occurring Menthol: A Useful Naturally Occurring Terpene Terpene Alcohol; Ethers as General Alcohol; Ethers as General Anesthetics; Marijuana: The Most Commonly Used Illicit Drug; Gar Anesthetics; Marijuana: The Most Commonly Used Illicit Drug; Garlic and lic and Onions: Odiferous Medicinal Plants Onions: Odiferous Medicinal Plants Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-3 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-4

Nomenclature of compounds Nomenclature of compounds Alcohol example Alcohol example containing functional groups containing functional groups The IUPAC system deals with functional The IUPAC system deals with functional C - C - C - C - C - C - C - O - O - H - H groups two different ways. groups two different ways. Modification of the hydrocarbon name to Modification of the hydrocarbon name to Base c contai ains ns 4 ca 4 carb rbon on indicate the presence of a functional group. indicate the presence of a functional group. - alka lkane nam ame is e is but butane alcohol, alcohol, - -OH OH use - use -ol ol ending. ending. - rem emove ove - -e e an and ad d add d - -ol ol ol ol ether: CH 3 CH 2 -O O- -CH CH 3 use methoxy methoxy ether: CH 3 CH 2 - use alcoho al cohol n name me - butan anol ol 3 methoxy ethane ethane methoxy OH is is on on t the firs first t ca carbon on so so - - thiol: R : R- -S S- -H H use - -thiol thiol ending. ending. thiol use 1 1- -bu bu butanol butanol Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-5 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-6 Alcohols - Alcohols - Structure Structure Alcohols - Alcohols - Nomenclature Nomenclature The functional group of an alcohol The functional group of an alcohol IUPAC names IUPAC names is an is an - -OH group bonded to an OH group bonded to an • the parent chain is the longest chain that contains the 3 hybridized carbon sp sp 3 hybridized carbon -OH group • number the parent chain in the direction that gives the • bond angles about the hydroxyl -OH group the lower number oxygen atom are approximately 109.5° • change the suffix -e e to -ol ol 3 hybridized Oxygen is also sp sp 3 hybridized Oxygen is also Common names Common names • two sp 3 hybrid orbitals form sigma • name the alkyl group bonded to oxygen followed by the bonds to carbon and hydrogen word alcohol alcohol • the remaining two sp 3 hybrid orbitals each contain an unshared pair of electrons Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-7 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-8

Alcohols Alcohols - - Nomenclature Nomenclature Alcohols - Alcohols - Nomenclature Nomenclature Problem: Write the IUPAC name of each alcohol Problem: Write the IUPAC name of each alcohol Compounds containing Compounds containing • two -OH groups are named as diols, (a) CH 3 ( CH 2 ) 6 CH 2 OH • three -OH groups are named as triols, etc. OH (b) OH CH 3 CHCH 2 CH 2 CHCH 2 CH 2 CH 2 (c) HO OH HO HO OH OH OH 1,2-Ethanediol 1,2-Propanediol 1,2,3-Propanetriol (Ethylene glycol) (Propylene glycol) (Glycerol, Glycerin) Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-9 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-10 Alcohols Alcohols - - Nomenclature Nomenclature Alcohols - Alcohols - Nomenclature Nomenclature Unsaturated alcohols Unsaturated alcohols Examples: Examples: OH • the double bond is shown by the infix -en en- OH OH • the hydroxyl group is shown by the suffix -ol ol Ethanol 1-Propanol 2-Propanol • number the chain to give OH the lower number (Propyl alcohol) (Isopropyl alcohol) (Ethyl alcohol) 6 4 2 OH OH 3 1 5 OH OH trans- 3-hexene-1-ol ( E )-3-hexene-1-ol 1-Butanol 2-Butanol 2-Methyl-1-propanol (Butyl alcohol) ( sec -Butyl alcohol) (Isobutyl alcohol) OH OH Cyclohexanol 2-Methyl-2-propanol (Cyclohexyl alcohol) ( tert -Butyl alcohol) Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-11 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-12

Name the alcohol Name the alcohol Common names Common names Ethyl alcohol Ethyl alcohol ethylene glycol ethylene glycol glycerol glycerol Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-13 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-14 Classification of alcohols Classification of alcohols Primary Primary Secondary Secondary Tertiary. Tertiary. Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-15 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-16

Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-17 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-18 Physical Properties Physical Properties Alcohols are polar compounds Alcohols are polar compounds • both the C-O and O-H bonds are polar covalent H δ - δ + C O δ + H H H Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-19 Chemistry 121, Winter 2008, LA Tech Chemistry 121, Winter 2008, LA Tech 1-20