Chemistry 121(01) Winter 2013
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;
Office Hours: MTW 9:00 am - 11:00 am;
TR 9:00 - 10:00 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
CHEM 121 Winter 2013
1
Chapter 14 and GHW#4
Questions
Introduction Alcohols, Phenols, and
Ethers:
Chapter 12. Saturated Hydrocarbons
12.1 Organic and Inorganic Compounds, 341
12.2 Bonding Characteristics of the Carbon Atom, 342
12.3 Hydrocarbons and Hydrocarbon Derivatives, 342
12.4 Alkanes: Acyclic Saturated Hydrocarbons, 343
12.5 Structural Formulas, 344
12.6 Alkane Isomerism, 346
12.7 Conformations of Alkanes, 348
12.8 IUPAC Nomenclature for Alkanes, 350
12.9 Line-Angle Structural Formulas for Alkanes, 356
12.10 Classification of Carbon Atoms, 358
12.11 Branched-Chain Alkyl Groups, 359
12.12 Cycloalkanes, 361
12.13 IUPAC Nomenclature for Cycloalkanes, 362
12.14 Isomerism in Cycloalkanes, 363
12.15 Sources of Alkanes and Cycloalkanes, 365
12.16 Physical Properties of Alkanes and Cycloalkanes, 367
12.17 Chemical Properties of Alkanes and Cycloalkanes, 368
12.18 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.
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)
d)
b)
c)
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. ( H2SO4 at 180)
Intermolecular dehydration : Water is removed from two alcohol
molecules and an ether is produced. ( H2SO4 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.