Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; Office Hours: MTW 9:00 am - 11:00 am; TR 9: :00 am & 1:00-2:00 pm. December 21, Test 1 (Chapters 12-14) January 18 Test 2 (Chapters 15-16) February 8 Test 3 (Chapters 17-19) February 25, Test 4 (Chapters 20-22) February 26, 2009, Make Up Exam: Bring Scantron Sheet 882-E Chemistry 121(01) Winter 2013 CHEM 121 Winter

Chapter 14 and GHW#4 Questions Introduction Alcohols, Phenols, and Ethers:

Chapter 12. Saturated Hydrocarbons 12.1 Organic and Inorganic Compounds, Bonding Characteristics of the Carbon Atom, Hydrocarbons and Hydrocarbon Derivatives, Alkanes: Acyclic Saturated Hydrocarbons, Structural Formulas, Alkane Isomerism, Conformations of Alkanes, IUPAC Nomenclature for Alkanes, Line-Angle Structural Formulas for Alkanes, Classification of Carbon Atoms, Branched-Chain Alkyl Groups, Cycloalkanes, IUPAC Nomenclature for Cycloalkanes, Isomerism in Cycloalkanes, Sources of Alkanes and Cycloalkanes, Physical Properties of Alkanes and Cycloalkanes, Chemical Properties of Alkanes and Cycloalkanes, Halogenated Alkanes and Cycloalkanes, 371

1. Bonding Characteristics of Oxygen Atoms in Organic Compounds

Structural Characteristics of Alcohols

1. Identify the Alcohols, Phenols, and Ethers from the following and give their common and/or IUPAC names.

2. Circle the constitutional isomers of 1- hexanol among following alcohols.

3. Classify each of the following as 1', 2', or 3' alcohols. a) b) c) d)

Chemical Reactions of Alcohols 1) Combustion: Alcohol are very flammable and the combustion products are carbon dioxide and water. 2) Substitution Reactions: OH group is replaced by a another group such as halogen. a) Elimination Reactions : Intramolecular dehydration : Water is removed from a alcohol molecule and a alkene is produced. ( H 2 SO 4 at 180  ) Intermolecular dehydration : Water is removed from two alcohol molecules and an ether is produced. ( H 2 SO 4 at 140  ) Williamson Ether synthesis.

4a. Complete the following reactions of alcohol. a) Dehydration:

4b) What is Zaitsev Rule?

Zaitsev’s rule (or the opposite of Markovnikov’s rule) Dehydration of an alcohol can result in more than one alkene product, because hydrogen loss can occur from either of the neighboring carbon atoms. Hydrogen is removed from the carbon with lowest hydrogen atoms ( poor get poorer)

5) Complete the following reactions of alcohol oxidation:

6) Draw condensed formula of each of the following: a.3-Hexanol b.1,2,3-Pentanetriol c.2-Methyl-2-pentanol d. Cyclohexanol e. 3,4-dimethyl-3-heptanol

6) Draw the alkene products of the dehydration of the following alcohols: a.3-Hexanol b.1,2,3-Pentanetriol c.2-Methyl-2-pentanol d. Cyclohexanol e. 3,4-Dimethyl-3-heptanol

7) Draw the alkene products of the dehydration of the following alcohols: a)2-Pentanol: b)3-Methyl-1-pentanol: c)2-Butanol: d)4-Chloro-2-pentanol: e)1-Propanol:

8) Give the oxidation products of the following alcohols. If no reaction occurs, write N.R.