Follow Up Questions from Chapter 13: Natural Polymers
Natural precursor
Natural Latex Rubber
Industrial precursor
Cellulose
Spider Silk
CHAPTER 14
Oxygen, Halogens, & Sulfur
General, Organic, & Biological Chemistry
Janice Gorzynski Smith
CHAPTER 14: Oxygen, Halogen, & Sulfur
Learning Objectives:
Name organic compounds with carbon-heteroatom single
bonds (oxygen, halogens, sulfur)
Identify 1°, 2°, 3° alcohols and alkyl halides
Predict the products or reactants for following reactions:
Alcohol dehydration
Alcohol oxidation
Sulfur oxidation
Sulfur reduction
3
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Functional
Groups
Overview
Alkyl
halides
Single Bond
to a
Heteroatom
Functional
Groups
Alcohols
Ethers
Thiols
4
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Alcohols
& Alkyl
Halides
1°, 2°, 3°
Alcohols
Nomenclature
#
1
2
3
4
5
6
7
8
9
10
OH
1
prefix +
prefix
6
4
2
3
5
parent +
suffix
Greek Straight Chain
Root Alkane Name
methane
meth
ethane
eth
propane
prop
butane
but
pentane
pent
hexane
hex
heptane
hept
octane
oct
nonane
non
decane
dec
First give location and type of substituents
Second give location of double bond
parent
How many carbons in longest chain?
suffix
How many of the functional group and
what is it? Alcohol = “ol”
2-methyl 4-
hexan
ol
#
Carbons
1
2
3
4
5
6
Alkyl Group
Structure
Name
CH3methyl
CH3CH2ethyl
CH3CH2CH2propyl
CH3CH2CH2CH2butyl
CH3CH2CH2CH2CH2pentyl
CH3CH2CH2CH2CH2CH2hexyl
*Note: after the greek root of the parent use “an”, ie hexan
* Second Note: when we have more then 1 multiple bond the parent name has an “a” after the greek root: hexa 6
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Functional
Groups
Alcohols
Fermentation
7
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Rxns of
Alcohols
Elimination Reaction: Dehydration
Zaitsev Rule:
The major product in
elimination is the
alkene that has more
alkyl groups bonded
to it.
Rxns of
Alcohols
Oxidations
Oxidation requires breaking C-H bonds and forming new C-O bonds. When
alcohol is the starting material the products always have a carbonyl group.
Rxns of
Alcohols
Alcohol Metabolism
Find notes from arthur’s explaination
Ethers
Nomenclature
#
1
O
prefix +
prefix
4
2
parent +
1
2
3
4
5
6
7
8
9
10
3
suffix
Use alkyl substitutant naming roots, but drop
the “yl” and use “oxy” for the simplest alkyl
group bonded to the ether oxygen.
parent
How many carbons in longest chain?
suffix
Use alkane ending: ane
2-ethoxy but ane
#
Carbons
1
2
3
4
5
6
Greek Straight Chain
Root Alkane Name
methane
meth
ethane
eth
propane
prop
butane
but
pentane
pent
hexane
hex
heptane
hept
octane
oct
nonane
non
decane
dec
Alkyl Group
Structure
Name
CH3methyl
CH3CH2ethyl
CH3CH2CH2propyl
CH3CH2CH2CH2butyl
CH3CH2CH2CH2CH2pentyl
CH3CH2CH2CH2CH2CH2hexyl
11
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Functional
Groups
Ethers
Diethyl Ether
The first anesthetic administered
in 1842 by Crawford Long
Heterocycles
O
12
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Thiols
Nomenclature
#
5
3
prefix +
parent +
prefix
SH
2
4
1
2
3
4
5
6
7
8
9
10
1
suffix
Greek Straight Chain
Root Alkane Name
methane
meth
ethane
eth
propane
prop
butane
but
pentane
pent
hexane
hex
heptane
hept
octane
oct
nonane
non
decane
dec
Give location and type of substituents, then
give location of thiol group.
parent
How many carbons in longest chain?
suffix
Hydrocarbon functional group suffix
+ “thiol”
2,4-dimethyl 1-
hept anethiol
#
Carbons
1
2
3
4
5
6
Alkyl Group
Structure
Name
CH3methyl
CH3CH2ethyl
CH3CH2CH2propyl
CH3CH2CH2CH2butyl
CH3CH2CH2CH2CH2pentyl
CH3CH2CH2CH2CH2CH2hexyl
13
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Functional
Groups
Thiols
Insulin
Jean-Philippe Cartailler, Ph.D. The Beta Cell Consortium
Smith. General Organic & Biolocial Chemistry 2nd Ed.
14
Rxns of
Thiols
Oxidation & Reduction
Alkyl Halides
Nomenclature
#
1
1
2
3
4
5
6
7
8
9
10
2
6
4
Cl
prefix +
prefix
3
5
parent +
suffix
Give location and type of substituents.
Replace “ine” in halide name with “o”, ie
Chlorine = chloro
parent
How many carbons in longest chain?
suffix
What is the hydrocarbon functional
group? If alkane then “ane” suffix
2-chloro 4-methyl
hex
ane
#
Carbons
1
2
3
4
5
6
Greek Straight Chain
Root Alkane Name
methane
meth
ethane
eth
propane
prop
butane
but
pentane
pent
hexane
hex
heptane
hept
octane
oct
nonane
non
decane
dec
Alkyl Group
Structure
Name
CH3methyl
CH3CH2ethyl
CH3CH2CH2propyl
CH3CH2CH2CH2butyl
CH3CH2CH2CH2CH2pentyl
CH3CH2CH2CH2CH2CH2hexyl
16
Smith. General Organic & Biolocial Chemistry 2nd Ed.
Functional
Groups
Alkyl Halides
Rxns of Alkyl
Halides
Substitution Reactions with Alkyl Halides
Substitution Reactions at 1° Carbons
Halides (Cl, Br) are good leaving groups (L) because they form very
polar covalent bonds with carbon.
Nucleophiles (Nu-) include negatively charged molecules or amines
(RNH2). Common Nucleophiles: NaOH ( OH-), NH3, RS-, I-.
Rxns of Alkyl
Halides
Substitution Reactions
Substitution Reactions at 1° Carbons
Substitution Reactions at 3° Carbons
Rxns of Alkyl
Halides
Substitution Reactions