Honors Chemistry
Unit 7A
Organic Chemistry
 Allotropes
 Isomers
 Hydrocarbons
o Alkanes
o Alkenes
o Alkynes
o Aromatics
 Alkyl Halides
1
2
3
4
Parent Chain:
Methane
CH4
Ethane
C2H6
Propane
C3H8
Butane
C4H10
Pentane
C5H12
Hexane
C6H14
Heptane
C7H16
Octane
C8H18
Nonane
C9H20
Decane
C10H22
Undecane
C11H24
Dodecane
C12H26
Branches (one less Hydrogen than Parent Chain):
all prefixes can be made into branches
Methyl
CH3
Ethyl
C2H5
5
Introduction of parent chain and branches
6
Organic Chemistry
 Hydrocarbons contain Carbon and Hydrogen only
 If all bonds on the carbons are single bondsdrocarbon
Alkanes


Have form CnH2n+2 (where n = # of carbons)
Ending of the name is “ane”
Name
Molecular
Structural Formula
Model
Formula
CnH2n+2
Methane
Ethane
Propane
Butane
2-Methylpropane
Example 1:
3-ethylheptane
7
Example 2:
2,7-dimethylnonane
Example 3:
4-ethyl-2,4,5-trimethyloctane
Example 4:
3,3,4,4-tetraethyl-2,2,5,5-tetramethylhexane
Cycloalkanes



All single bonds
Have form CnH2n
Ends of chain bond together (lose 2 hydrogens)
Examples:
8
More practice Naming Alkanes
Drawing Alkanes
9
Unsaturated Hydrocarbons
= not all carbons have 4 single bonds
(double or triple bonds)
Alkenes


Structure contains double bonds
Have form CnH2n
Name
Molecular
Structural Formula
Model
Formula
CnH2n
Ethene
Propene
2-Butene
Drawing and naming Alkene structures:
10
More drawing and naming alkenes
11
Alkynes

Structure contains triple bonds

Have form CnH2n-2
Name
Molecular Formula
Structural Formula
CnH2n-2
Ethyne
1-Propyne
1-Butyne
Naming and drawing Alkynes:
12
Aromatic Hydrocarbons
Mu
st contain at least one benzene ring

Naming Aromatics
13
Date__________
Name ____________________________________ Class ______
Modern Chemistry Lab Practical
Unit on "Organic Chemistry"
I. Problem: What are some of the differences between various organic compounds? You will be given some notes and
then asked to design a model of these organic compounds including: alkanes, isomers of alkanes, alkenes, alkynes,
alcohols, organic acids, aldehydes, ketones and some nitrogen containing organic compounds.
II. Background Information: Alkanes are saturated hydrocarbons with a formula of CnH2n+2. Isomers of alkanes
would have the same formula but different structures. Other information will be given at the beginning of each day
of this lab practical.
III. Hypothesis:
IV. Test The Hypothesis:
Materials: make certain your kit contains the following in the right location. If it does not, the previous user will be
marked at least 1 point off their next assignment grade each day there is a problem. Each day you work
with the kit, you are to sign the paper in the kit with your class numbers and date.
10 black spheres 2 blue spheres 28 yellow spheres 6 red spheres 4 green spheres 2 orange spheres 2 white spheres2 purple spheres-
carbon
\ place these on the small side of your kit
nitrogen /
hydrogen \
oxygen
\
chlorine
\ place these on the larger side
bromine
/ of your kit
fluorine /
(all colors are to be placed together)
iodine
/
30 small wooden pegs - H bonds only
\
10 large wooden pegs - other single bonds
\ place these in the
9 metal springs double or triple bonds
/ center of your kit
or stress bonds /
V. Observations: The first student lab team that has the structure correct will be initialed by the instructor and receive a
grade of 2 points out of 1 point. These students will then have their names placed on the board and will be
teaching assistants for that organic structure. They will be responsible to grade and initial the structures of
other lab teams. Each structure that is designed and named by you is worth 1 point. The following is the
grading criteria:
2 points
= graded by the instructor and perfect, this team assists in grading
1 point
= other perfect scores
0 points
= 1 or more mistakes in the structure and/or name
14
Assignment # ____
Name ____________________________________
Class Number ______
Date ________
Name ____________________________________
Class Number ______
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Alkanes – Straight and Branched
(If absent - write an I-search paper describing the major uses of each of the first 10 alkanes. This must be written in the first
person. Answer the 3 questions on page 16 using the criteria of an I-Search.)
(2 points, ½ point each)
Grade/Initials
_______________ 1.
hexane
_______________ 2.
3-methylpentane
_______________ 3.
2, 4-dimethylhexane
_______________ 4.
2, 2-dimethylpentane
_______________ Bonus ½ Point: 3-ethyl-2, 4-dimethylhexane
(only for 1st three teams who are correct, one attempt per team)
_______________ 1 point lost for problems with your kit
/2
_______________Total points for Straight and Branched Alkanes
15
Information on Doing an “I-Search” Paper to Make-Up a Missed Organic Chem Modeling Lab:
1. An "I-Search” paper is telling the story of what you did in your search, those happenings and
facts crucial to your hunt for information on your assigned topic.
You are to write 150 words (one page) for each modeling lab you miss.
2. The paper is to be typed and divided into three parts (each section is to be titled as below):
a. What I knew before I started my search.
b. The facts I found in my search and what I learned.
c. What I found the most interesting with what I learned.
3. If your make-up paper does not answer these questions, the best score you can receive
is half credit.
16
Name ______________________________________________
Alkane Worksheet
Based on the given IUPAC name, give the structural formula for each of the following
molecules (number the carbons):
Name
Structural Formula
1.
dodecane
2.
2-methylheptane
3.
2,3,4-trimethylhexane
4.
3-methylpentane
5.
3-ethyl,2,4,4-trimethylnonane
6.
3-butyl,2,4-diethyl,1-methyl cyclobutane
17
Give the IUPAC name for each of the following molecules (number the carbons):
Name
Structural Formula
1.
CH3-CH2-CH2-CH2-CH2-CH2-CH3
2.
CH3

CH3-CH-CH2-CH3
3.
CH3
CH3 CH3



CH3-CH-CH2-CH-CH-CH3
4.
CH2-CH3

CH3
5.
6.
CH3
CH3


CH2
CH2


CH3-CH2-CH-CH2-CH2-CH-CH2-CH3
CH3
CH3
CH3



CH2 CH2
CH2



CH3-CH-CH-CH2-CH2-CH-CH2-CH3
18
Introduce Isomers
19
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Isomerism
(If absent - write an I-search paper on organic isomers. This must be written in the first person. Answer the 3 questions on
page 16 concerning an I-Search.)
(2 points, ½ point each)
Grade/Initials: Do not use –iso or –neo. Use the naming system found in 19.4.
_______________ 1. butane isomer #1
(simple)
(0.25 point)
name _____________________________________
(0.25 point)
_______________ 2. butane isomer #2
(one branch) (0.25 point)
name _____________________________________
(0.25 point)
_______________ 3. pentane isomer #2
(one branch) (0.25 point)
name _____________________________________
(0.25 point)
_______________ 4. pentane isomer #3
(two branches) (0.25 point)
name _____________________________________
(0.25 point)
_______________ Bonus ½ Point: any isomer of hexane Name ___________________________________
not done by another team
put the name on the board) (0.25 point)
(Teacher checks) (0.25 point)
_______________ 1 point lost for problems with your kit
/ 2
_______________ Total points for Isomerism
20
Name _____________________________________________
Draw and name the 18 isomers of Octane
Octane:
1.
Methyl heptane:
1.
2.
3.
Dimethyl hexane:
1.
2.
3.
4.
5.
6.
21
Ethyl hexane:
1.
Trimethyl pentane:
1.
2.
3.
4.
Methyl ethyl pentane:
1.
2.
Tetramethyl butane:
1.
22
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Unsaturated Hydrocarbons
(If absent - write an I-search paper unsaturated hydrocarbons. This must be written in the first person. Answer the 3 questions
on page 16 of your packet.)
(3 points, ½ point each)
Grade/Initials
_______________ 1.
1-butene
_______________ 2.
2-butyne
_______________ 3.
2-methylpropene
_______________ 4.
3-methylbutene
_______________ 5.
1, 3-pentadiene
_______________ 6.
4-methylpentyne
_______________ Bonus ½ Point: chloroethene (the monomer of polyvinyl chloride)
((1st three groups correct get bonus point) ( one attempt per team)
(Teacher checks)
_______________ 1 point lost for problems
/ 3
_____________ Total points for Unsaturated Hydrocarbons
23
24
Name ______________________________________________
Alkene Alkyne Assignment
Based on the given IUPAC name, give the structural formula for each of the following molecules
(number the carbons):
Name
Structural Formula
1.
3-heptene
2.
3-methyl-butyne
3.
4,5,5-trimethyl-1-hexene
4.
3-ethyl-2,4-dimethyl-2-pentene
5.
5-methyl-1,3-hexadiyne
6.
1,2,4-trimethyl-1-cyclopentene
7.
2,4,5-trimethyl-1,3-cyclohexadiene
25
Give the IUPAC name for each of the following molecules (number the carbons):
Name
Structural Formula
1.
C–C–C=C-C-C
2.
C

C=C–C–C-C
3.
C
C


C-C-C - C-C=C
4.
5.
6.
C
C–C-C
C
C


C
C


C -C = C–C=C-C–C
C C
 
C C C
  
CΞC-C - C-C -C≡C
7.
C
C -C
26
Alkyl Halides:
 Organic compound with
 General Formula
o
o
o
o
–
–
–
–
 Naming:
o
Name as if the halogen is a branch
Examples:
27
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Mixed Aromatic Hydrocarbons, Alkyl Halides and Hydrocarbons
(If absent - write an I-search paper unsaturated hydrocarbons. This must be written in the first person and be 150 words.
Answer the 3 questions on page 16 of your packet concerning an I-Search.)
(3 points, ½ point each)
Grade/Initials
_______________ 1.
2-chloropropane
_______________ 2.
2-bromo-3,4 -dichloropentene
_______________ 3.
5-bromo-1- chloro-4,4-diiodo-5-methyl-2- hexyne
_______________ 4.
ethylbenzene
_______________ 5.
1-ethyl-3-methylbenzene
_______________ 6.
1,2,4-trimethylbenzene
_______________ 1 point lost for problems with your kit
/ 3
_____________ Total points for Aromatics and Alkyl Halides
28
Alkane, Alkene, Alkyne, Cyclos and Aromatic Review Sheet
Section 1: Draw the following structures:
1. 1-ethyl-2-methyl-cyclohexane
2. 2,3-dimethyl-1,5-heptadiene
3. 3-bromo-4,5-dichloro-6-iodo-undecane
4. 1-butyl-3-propyl-benzene
5. 3.3.4-trifluoro-1,6-octadiyne
6. 1-ethyl-4-methyl-1,3-cycloctadiene
7. 1-bromo-5,6-dichloro-3-fluoro-2,4-dimethyl-benzene
29
30
Assignment # ____
Date ________
Name ____________________________________ Class Number ________
Name ____________________________________ Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Mixed Hydrocarbons
_______________ 1. 2, 3, 4-trimethylhexane
_______________ 2. propylcyclobutane
_______________ 3. Methylbenzene
_______________ 4. 1,1-difluoro-2-butyne
_______________ 5. 1-iodi-2-methylpropene
_______________ 6. 1, 3-pentadiene
_______________ 7. 1-bromo-1-chlorobutyne
_______________ 8. 1-chloro-2-ethyl-3fluoro-cyclohexene
/ 8
_______________ Total points for Mixed Hydrocarbons
31
32
Petroleum
Oil and natural gas touch our lives in countless ways every day.
Together, they supply 65 percent of our nation’s energy. They fuel
our cars, heat our homes and cook our food. But did you know that
oil and natural gas also help generate the electricity that powers
our daily lives? Or that crude oil supplies the building blocks for
everything from dent-resistant car fenders to soft drink bottles to
camping equipment?
“Hy”-CARB
Crude oils are mixtures of many different substances, often difficult to separate, from which various
petroleum products are derived, such as: gasoline, kerosene propane, fuel oil, lubricating oil, wax, and
asphalt. These substances are called hydrocarbons. Hydrocarbons may be gaseous, liquid, or solid at
normal temperature and pressure, depending on the number and arrangement of the carbon atoms in their
molecules. Those with up to 4 carbon atoms are gaseous; those with 20 or more are solid; those in
between are liquid. Crude oils are liquid but may contain gaseous or solid compounds (or both) in
solution. The heavier a crude oil (i.e. the more carbon atoms its molecules contain) the closer it is to being
a solid and this may be especially noticeable as its temperature cools. Light oils will remain liquid even at
very low temperatures.
Crude “Development”
Oil is formed from the remains of tiny plants and animals (plankton) that died in ancient seas between 10
million and 600 million years ago. After the organisms died, they sank into the sand and mud at the bottom
of the sea. Over the years, the organisms decayed in the sedimentary layers. In these layers, there was
little or no oxygen present. So microorganisms broke the remains into carbon-rich compounds that formed
organic layers. The organic material mixed with the sediments, forming fine-grained shale, or source rock.
As new sedimentary layers were deposited, they exerted intense pressure and heat on the source rock.
The heat and pressure distilled the organic material into crude oil and natural gas. The oil flowed from the
source rock and accumulated in thicker, more porous limestone or sandstone, called reservoir rock.
Movements in the Earth trapped the oil and natural gas in the reservoir rocks between layers of
impermeable rock, or cap rock, such as granite or marble.
33
Black gold, Texas tea!
Crude oil is the term for "unprocessed" oil, the stuff that comes out of the ground. It is also known as
petroleum. Crude oils vary in color, from clear to tar-black, and in viscosity, from watery to almost solid.
Crude oils are such a useful starting point for so many different substances because they contain
hydrocarbons. Hydrocarbons are molecules that contain hydrogen and carbon and come in various lengths
and structures, from straight chains to branching chains to rings.
There are two things that make hydrocarbons exciting to chemists:
o
o
Hydrocarbons contain a lot of energy. Many of the things derived from crude oil like gasoline,
diesel fuel, paraffin wax and so on take advantage of this energy.
Hydrocarbons can take on many different forms. The smallest hydrocarbon is methane (CH4),
which is a gas that is a lighter than air. Longer chains with 5 or more carbons are liquids. Very long
chains are solids like wax or tar. By chemically cross-linking hydrocarbon chains you can get
everything from synthetic rubber to nylon to the plastic in tupperware. Hydrocarbon chains are
very versatile!
The major classes of hydrocarbons in crude oils include:
Alkanes: methane, ethane, propane, butane, pentane, hexane
Aromatics: benzene, napthalene
Cycloalkanes: cyclohexane, methyl cyclopentane
Alkenes: ethylene, butene, isobutene
Divide and Conquer
The problem with crude oil is that it contains hundreds of different types of hydrocarbons all mixed
together. You have to separate the different types of hydrocarbons to have anything useful. Fortunately
there is an easy way to separate things, and this is what oil refining is all about. Refining crude oil involves
two kinds of processes to produce the products so essential to modern society. First, there are physical
processes that simply refine the crude oil (without altering its molecular structure) into useful products
such as lubricating oil or fuel oil. Second, there are chemical or other processes that alter the molecular
structure and produce a wide range of products, some of them known by the general term petrochemicals.
Chain Gang
The oil refining process starts with a fractional
distillation column.
Different hydrocarbon chain lengths all have
progressively higher boiling points, so they can all be
separated by distillation. In an oil refinery, crude oil is
heated and the different chains are pulled out
according to their vaporization temperatures. Each d
ifferent chain length has a different property that
makes it useful in a different way.
34
“Piece” Out
To understand the diversity
contained in crude oil, and to
understand why refining crude oil is
so important in our society, look
through the following list of products
that come from crude oil:
Petroleum gas - used for heating, cooking,
making plastics
small alkanes (1 to 4 carbon
atoms)
o boiling range = less than 104
degrees Fahrenheit / 40
degrees Celsius
o often liquefied under pressure
create LPG (liquefied petroleum gas)
Naphtha or Ligroin - intermediate that will be further processed to make gasoline
o
to
o mix of 5 to 9 carbon atom alkanes
o boiling range = 140 to 212 degrees Fahrenheit / 60 to 100 degrees Celsius
Gasoline - motor fuel
o liquid
o mix of alkanes and cycloalkanes (5 to 12 carbon atoms)
o boiling range = 104 to 401 degrees Fahrenheit / 40 to 205 degrees Celsius
Kerosene - fuel for jet engines and tractors; starting material for making other products
o
o
o
Gas oil
liquid
mix of alkanes (10 to 18 carbons) and aromatics
boiling range = 350 to 617 degrees Fahrenheit / 175 to 325 degrees Celsius
or Diesel distillate - used for diesel fuel and heating oil
o liquid
o alkanes containing 12 or more carbon atoms
o boiling range = 482 to 662 degrees Fahrenheit / 250 to 350 degrees Celsius
Lubricating oil - used for motor oil, grease, other lubricants
o
o
o
Heavy
liquid
long chain (20 to 50 carbon atoms) alkanes, cycloalkanes, aromatics
boiling range = 572 to 700 degrees Fahrenheit / 300 to 370 degrees Celsius
gas or Fuel oil - used for industrial fuel; starting material for making other products
o liquid
o long chain (20 to 70 carbon atoms) alkanes, cycloalkanes, aromatics
o boiling range = 700 to 1112 degrees Fahrenheit / 370 to 600 degrees Celsius
Residuals - coke, asphalt, tar, waxes; starting material for making other products
o
o
o
solid
multiple-ringed compounds with 70 or more carbon atoms
boiling range = greater than 1112 degrees Fahrenheit / 600 degrees Celsius
35
Break it Down!
Very few of the components come out of the fractional distillation column ready for market. Many of them must be
chemically processed to make other fractions. For example, only 40% of distilled crude oil is gasoline; however,
gasoline is one of the major products made by oil companies. Rather than continually distilling large quantities of
crude oil, oil companies chemically process some other fractions from the distillation column to make gasoline; this
processing increases the yield of gasoline from each barrel of crude oil.
Chemical Processing
You can change one fraction into another by one of three methods:
o
o
o
Cracking - breaking large hydrocarbons into smaller pieces.
Unification - combining smaller pieces to make larger ones.
Alteration - rearranging various pieces to make desired
hydrocarbons.
Cracking up
Cracking breaks large chains into smaller chains.
There are several types of cracking:
Thermal - you heat large hydrocarbons at high temperatures
(sometimes high pressures as well) until they break apart.
Coking - residual from the distillation tower is heated to
temperatures above 900 degrees Fahrenheit/482 degrees
Celsius until it cracks into heavy oil, gasoline and
naphtha. When the process is done, a heavy, almost
pure carbon residue is left (coke); the coke is cleaned
from the cokers and sold.
Catalytic - uses a catalyst to speed up the cracking reaction.
Catalysts include zeolite, aluminum hydrosilicate,
bauxite and
silica-alumina.
After various hydrocarbons are cracked into smaller hydrocarbons, the
products go through another fractional distillation column to separate them.
Come together
Sometimes you need to combine smaller hydrocarbons to make larger ones - this process is called unification. The major unification process is called
catalytic reforming and uses a catalyst (platinum) to combine low weight
naphtha into aromatics, which are used in making chemicals and in blending
gasoline. Sometimes, the structures of molecules in one fraction are
rearranged to produce another. Commonly, this is done using a process
called alkylation. In alkylation, low molecular weight compounds, such as
propylene and butylene, are mixed in the presence of a catalyst such as
hydrofluoric acid or sulfuric acid. The products of alkylation are high
octane hydrocarbons, which are used in gasoline blends.
36
Take it to the Cleaners
Distillated and chemically processed fractions are then treated to remove impurities, such as organic compounds
containing sulfur, nitrogen, oxygen, water, dissolved metals and inorganic salts. Treating is usually done by passing
the fractions through the following:
A column of sulfuric acid - removes unsaturated hydrocarbons (those with carbon-carbon double-bonds),
nitrogen compounds, oxygen compounds and residual solids (tars, asphalt)
o An absorption column filled with drying agents to remove water
o Sulfur treatment and hydrogen-sulfide scrubbers to remove sulfur and sulfur compounds
After the fractions have been treated, they are cooled and then blended together to make various products, such as:
o
o
o
o
o
o
o
o
Gasoline of various grades, with or without additives
Lubricating oils of various weights and grades (e.g. 10W-40, 5W-30)
Kerosene
Jet fuel
Diesel fuel
Heating oil
Chemicals of various grades for making plastics and other polymers
Burn Baby Burn!
Alkanes are less reactive than other hydrocarbons because of the stability of
their single covalent bonds. One reaction alkanes do undergo is combustion. Because alkanes make up a large portion
of gaseous and liquid fossil fuels, combustion is their most important reaction. Complete combustion of
hydrocarbons produces energy, CO2, and H2O. The reaction for combustion of methane produces 890kJ/mol of
energy.
CH4 + 2 O2  CO2 + 2 H2O
One concern about the combustion of fossil fuels is their possible contribution
to the greenhouse effect. CO2 is one of the atmospheric molecules that absorbs
infrared radiation. Increased levels of CO2 through the combustion of fossil fuels may
increase the amount of infrared energy absorbed by the atmosphere to a level that
can increase the average temperature of Earth.
Engines can be powered by gasoline combustion. When fuel ignites
spontaneously before it is reached by the flame front, there is a decrease in the
amount of power gained, and engine knocking results. Straight-chain hydrocarbons are
more likely to ignite spontaneously than branched-chain hydrocarbons. This tendency
is the basis for the octane rating scale. The octane rating of a fuel is a measure of
its burning efficiency and its antiknock properties. The octane rating scale is based on
mixtures of 2,2,4-trimethylpentane, a highly branched alkane, and heptane, a straightchain alkane. The term octane comes from the common name of 2,2,4trimethylpentane, isooctane. Pure 2,2,4-trimethylpentane is very resistant to knocking
and is assigned an octane number of 100. Pure heptane has an octane number of 0 and
burns with a lot of knocking. Increasing the percentage of branched-chain alkanes in gasoline is one way to increase
octane rating. The octane rating on gasoline pumps is shown in the figure to the right
37
38
Name ____________________
“Fuel” for Thought!
1. Indentify/sort the hydrocarbons that are gas, liquid, or solid at room temperature.
Gas
Solid
Liquid
2. Describe the conditions necessary to form crude oil.
3. Identify the components of gasoline (or petrol as the Australians say).
4. Describe different methods used to increase the amount of gasoline obtained from crude oil.
5. Describe how various impurities are removed from the fractions of crude oil.
39
6. Identify and describe how you use 5 products made from crude oil.
7. What does the octane rating mean?
8. What does a high octane number indicate about the composition (the hydrocarbons)?
40
Other Organic Compounds
 Functional Group –
 Same Functional Group
o
o
-
Alcohols:
 Organic compound that
 General Formula
 Naming:
o
If no number is present in front of the name – presume the –OH is on carbon number 1.
o
If 1 -OH group
 -
Examples:
o
If two or more -OH groups
 2=
 3=
 4=
 Keep the ane; add the appropriate ending listed above:
Examples:
41
Classification of Alcohols:
For classification –
If that carbon is attached to one other carbon, it is called a
______________
 C - C - C - OH
If that carbon is attached to two other carbons, the compound is called a ________________________

OH

C-C-C-C
If that carbon is attached to three carbons, it is called a ____________________
OH

C-C-C–C

C
42
Ethers:

Organic compounds

General Formula:
- R and R’
 Naming:
o–
o–
o–
Examples:
43
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Alcohols and Ethers
(If absent:- Write an I-search paper describing an alcohol or ether and how it is used in everyday life. This must be written in
the first person. See page 16 of the packet for questions to answer.)
(5 points)
Grade/Initials
_______________ 1. 2-methylpropanol
_______________ 2. 2-propanol (rubbing alcohol)
_______________ 3. 1,2,3-propanetriol
______________ 4. Butyl ethyl ether
_______________ 5. Dicyclopentyl ether
+1 Bonus:
_______________ design an alcohol
with 5 carbons total
name _____________________________
(can not be straight chain)
put the name on the board, others may not use
(must be done today)
_______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above.
(Your total will change if the above is not done)
/ 5
_______________ Total points for Alcohols and Ethers
44
Name__________________________________________
Other Organic Compounds – WS I
Draw the following compounds (number the parent chain and circle any branches):
1. 1,8 nonanediol
4. dibutyl ether
2. 1, 3, 5 trimethylbenzene
5. 4-decanol
7. 1,2dibromo -1-chloroethane
3. 2-bromo-2-fluoro prppane
6. 1-iodocyclobutane
8. 4-ethyl -3,6-difluoro-5-propyl-1-cyclohexene
9. 2,3-dichloro-7,8,9-triiodo-6,7,8-tripropyl-4-dodecene
10. 1,2,3,4,5,6-hexafluoro-1-hexanol
11. Decyl octyl ether
45
46
Other Organic Compounds
Continued
Carbonyl group is C=O
Aldehydes:
 Organic compounds
 General Form:
O

R–C–H
 Naming:

-
Example
O

C-C-H
lanthte
47
Ketones:
 Organic compound
 General Form:
O

R – C – R’
 Naming:
Example:
O

C–C-C
2-propanone
48
Carboxylic Acids:
O

- C – OH
Carboxyl group is
Organic compounds

 General Form:
O

R – C - OH
 Naming:
o If one carboxyl group
o If more than one carboxyl group
 For 2 = dioic acid
 For 3 = trioic acid
 For 4 = tetraoic acid
Example:
HOOC-C-C-COOH 1,4-butanedioic acid
49
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Aldehydes and Ketones
(If absent:- Write an I-search paper describing an aldehyde or ketone and how it is used in everyday life. This must be written
in the first person. See page 16 for details of an I-search.)
(5 points)
Grade/Initials
_______________ 1. propanone (acetone)
_______________ 2. 2-methylpropanal
_______________ 3. 2,2-dimethylpentanal
_______________ 4. methanal (formaldehyde)
_______________ 5. 2-pentanone
+1 Bonus Point:
_______________ design an aldehyde or ketone
with 5 carbons total
name ____________________________________
(can not be straight chain)
put the name on the board, others may not use
(must be done today)
/ 5
_______________ Total points for Aldehydes and Ketones
______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above. (Your
total will change if the above is not done)
50
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Carboxylic Acids
(If absent:- Write an I-search paper describing a carboxylic acid and how it is used in everyday life. This must be written in
the first person. See page 16 for details of an I-search.)
(5 points)
Grade/Initials
_______________ 1. butanoic acid
_______________ 2. 3-methylpentanoic acid
_______________ 3. 3, 3-difloro-4-ethylhexanoic acid
_______________ 4. 2-butylpropanedioc acid
_______________ 5. 4-ethyl-2-methylheptanoic acid
_______________ Bonus Point: design an acid
with 5 carbons
name __________________________
(put the name on board, others may not use)
(cannot be straight chain, must be done today)
/ 5
_______________ Total points for Carboxylic Acids
_______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above.
(Your total will change if the above is not done)
51
52
Name__________________________________________
Other Organic Compounds – WS II
Draw the following compounds (number the parent chain and circle any branches):
1. 1,5 pentanedioic acid
4. 1,2,4 tributyl benzene
7. 1,2-dichlorocyclohexane
9. 3-iodo-1-propanal
2. 1 heptanal
3. 3-hexanone
5. 3,5 dimethyl- 4 propyl octane
6. Butyl methyl ether
8. Dicyclopentylmethanone
10. 4,5,6,7-tetrabromo -3,8 dichloro -5,6-diethyl-3,8-dimethyl-1,10-decanedioic acid
53
54
More Organic Compounds
Continued (again)!
Esters:
Organic compounds
O

R - C - OH
(Acid)
O

 R - C - O - R’
(Ester)
Naming:
 Parent Chain
o
o
o
o
 Branches
o
o
Example:
O

C - C - O - C - C-C
2 1
1 2 3
(Parent)
(Alkyl branch)
55
Parent Chain:
Branch:
Final Name:
Example:
O

C - C - C - C - O - C - C
4 3 2 1
1 2
Parent Name:
Branch:
Final Name: ____________________
Draw: Pentyl Hexanoate
56
Amines:
Organic compounds based on NH3
R - N - R”

R’
Naming:


Primary amine:
(______ hydrogen is replaced by an alkyl group)
C–N–H

H
Name: ___________________________
Secondary amine:
(____ hydrogens are replaced by alkyl groups)
C–N–C - C

H
Name: _____ ______ _______________
Tertiary amine:
(____ hydrogens are replaced by alkyl groups)
C–N–C - C

C–C-C
57
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
Esters and Amines
(If absent:- Write an I-search paper describing an ester or amine and how it is used in everyday life. This must be written in
the first person. See page 16 for details of an I-search.)
(5 points)
Grade/Initials
_______________ 1. butylamine
_______________ 2. ethylpropylamine
_______________ 3. ethylmethanoate (an ester)
Design one of the following for 2 points, if right it is placed on the board and other teams may not use it:
_______________ 4. design an ester
with 5 carbons total
name _____________________________________
(can not be straight chain)(Instructor checks)
_______________ 5. design an ester
with 7 carbons total
name _____________________________________
(can not be straight chain)(Instructor checks)
_______________ +1 Bonus Points: pentylethanoate (banana flavoring)
(must be done today)
/ 5
_______________ Total points for Esters/Amines
_______________ 1 point lost for pieces missing from your kit, above not filled-in completely or not totaled on the line above.
(Your total will change if the above is not done)
58
Name: __________________________________________________
Ester and Amine Worksheet
Draw each of the following compounds:
1. ethyl butanoate
4. diethylamine
2. propyl-benzoate
5. butylethylpropylamine
7. methyl-2-methylhexanoate 8. propyl pentanoate
3. propylamine
6. hexyloctylamine
9. phenyl butanoate
59
60
Organic Compounds
Family
Functional Group
Ending
Naming
Alkane
Alkene
Alkyne
Aromatic
Alkyl halides
Alcohol
61
Family
Functional Group
Ending
Naming
Ether
Aldehyde
Ketone
Carboxylic Acid
Ester
Amine
62
Assignment # ____
Name ____________________________________
Class Number ________
Date ________
Name ____________________________________
Class Number ________
Kit # _______
Honors Chemistry Lab Practical
"Organic Chemistry"
ALL Mixed Up
Grade/Initials
_______________ 1. 4-methyl-2,3-octanediol
_______________ 2. 3-chloro-3-ethyl-2,2,4-trimethylpentane
_______________ 3. 3-propylhexanoic acid
______________ 4. Butyl methyl propyl amine
_______________ 5.
Pentyl propyl ether
_______________ 6. 1-bromo-4-iodo-2-propylbenzene
_______________ 7. 6,6-difluoro-3-methyl-3-propyl-1,4-hexadiyne
_______________ 8. 3-methyl-2,2-difluorobutanal
_______________ 9. 4-ethyl-6-iodo-3,3-dimethyl-1-cyclohexene
_______________ 10. Propylbenzoate
_______________ 11. 5-fluoro-2-methyl-3-hexanone
_______________ 12. 1-fluoro-2-methyl-3-hexanone
Total Points =
/ 6
63
64
Name: __________________________________________________
Mixed Worksheet
Draw each of the following structures:
1. 1-chloro-2-pentyl-4-propyl benzene
3. 2-iodo-3-methyl butanedial
5. propyl undecyl ether
7. 2,5-dimethyl-1-cyclopentanone
9. 1,4,9,11-dodecanetetrol
2. 5-fluoro-2-octyne
4. 5,5-dibromo-1,1,1-trifluoro-8-ethyldecane
6. 1,3,6-heptatriene
8. 2,3,4,5,6-pentafluoro-1-nonanal
10. 4-bromo-5-butyl-3-ethyl-1-cycloheptyne
65
66
Name ___________________________________________________________
Review for Organic Quest
Part 1: Draw and name each of the six models:
#1
#2
Name
Name
#3
#4
Name
Name
#5
#6
Name
Name
67
Part 2: Draw the following structures:
1. 1,4,7-octanetriol
2. 2,4-dibromo-3-fluoro-1-hexene
3. heptyl hexyl ether
4. butyl pentanoate
5. 3-chloro-5-ethyl heptanal
6. dodecane
7. 4-bromo-5,5-difluoro-3-decanone
8. butyl ethyl pentyl amine
9. 2,3-dimethyl 4-nonene
10. 1-bromo-4-butyl-2-ethyl-3 propyl benzene
11. 1,4,5,trichloro-2-pentyne
12. 2,3,5,7,9 pentabromo-1,4,8-trichloro-6,6 diiodo undecane
68
69
70
Polymers
The word comes from the Greek polumeres, which means `having many
parts. Polymers are large molecules consisting of repeated chemical
units (‘monomers') joined together, usually in a line, like beads on a
string. Each `mer' is typically made up of more than 5 and less than
500 atoms; the word `polymer' is applied when you have more than
about 50 `mers' stuck together. Your body is made of polymers. Amino
acids (proteins) and nucleic acids (RNA and DNA), the genetic blueprint
that defines people and other living things, are polymers, as well as
cellulose and starches in the foods we eat. The most powerful
computers - our brains - are mostly just a polymer glob soaking in salty
water! The wheels on our skateboards and in-line skates, tires on our
bikes and cars, various plastic containers, and clothing are just a few
other examples. In fact, polymers surround us every day everywhere
we go.
Two important polymeric materials are plastics and elastomers. Plastics are a large and varied group of
synthetic materials, which are processed by forming or molding into shape. We have many types of plastics
such as polyethylene and nylon. Plastics can be divided into two classes, thermoplastics and thermosetting
plastics, depending on how they are structurally and chemically bonded. Elastomers or rubbers can be
deformed when a force is applied to them and can return to their original shape (or almost) when the force
is released.
Some Naturally Occurring Polymers
Lac
The insect Laccifer lacca—or just plain “lac”—lives on trees in India and Southeast Asia. It secretes a resin,
also called lac, a polymer from which people make lacquer and shellac. They use these varnishes to coat
ships, houses, furniture, fruit, pills, and candy.
Rosin
Dead wood and pulp from pine trees contain a polymer called rosin, which is used to make varnish and soap.
Violinists rub rosin on the horsehairs in their bows to make them slide smoothly across the strings.
Gymnasts and baseball players use rosin to improve their grips.
71
Latex
South American Indians slash the bark of trees in the
rain forest to obtain a milky white fluid called latex. They
discovered that it could form a solid that was elastic; you
could stretch it and it would snap back to its original
shape. If you rubbed it on penciled words, the writing
would disappear, so Europeans called it rubber. They
molded it into tires for carriages and automobiles.
Milk
Drink up! Cow’s milk is loaded with the polymer casein, a
protein. Without this polymer, cheese would come unglued.
Glue would come unglued too, since casein from milk
provides its sticking power. Casein also winds up in
buttons, as well as rhinestones and other artificial
In 1839 Charles Goodyear discovered
that latex heated with sulfur—or
“vulcanized”—would remain elastic at a
wide range of temperatures. Although
Goodyear didn’t know why his invention
worked, we do today: The sulfur made
bridges between the long chain polymers
in rubber to keep them from sliding past
one another or contracting into knots.
gemstones.
Amber
Fossilized tree sap made of resin polymers can become yellow, orange, or brown amber.
Ancient Greeks called amber “elektron,” and its ability to give a static electrical shock
gave electrons and electricity their names. Scientists have retrieved intact genetic
polymers, DNA, from ancient insects trapped in amber. Some even think the tiny
bubbles in amber might hold the last remaining samples of air breathed by dinosaurs
more than 60 million years ago.
Silkworm
Silkworms, which are actually caterpillars, are raised on silk farms and fed mulberry leaves.
People in China discovered more than 4,500 years ago that they could unravel silk, a polymer,
from the worms’ cocoons and weave it into soft fabrics. Incredibly, a single cocoon yields
330 to 980 yards (300 to 900 meters) of silk. For centuries, silk was so prized that
exporting mulberry seeds or silkworm eggs from China was punished by death.
Styrofoam
Polystyrene foam can be made into cartons to protect eggs or into packing “peanuts” to cushion
fragile objects for shipping. It insulates, so folks put drinks in foam cups and coolers to keep
the warm ones warm and the cold ones cold.
72
Types Of Polymers
Polymers are formed by chemical reactions in which a large number of molecules called monomers
are joined sequentially, forming a chain. In many polymers, only one monomer is used. In others,
two or three different monomers may be combined. Polymers are classified by the characteristics
of the reactions by which they are formed. If all atoms in the monomers are incorporated into the
polymer, the polymer is called an addition polymer. If some of the atoms of the monomers are
released into small molecules, such as water, the polymer is called a condensation polymer.
Copolymers
The synthesis of macromolecules composed of more than one monomeric repeating unit has been explored
as a means of controlling the properties of the resulting material. In this respect, it is useful
to distinguish several ways in which different monomeric units might be incorporated in a polymeric
molecule. The following examples refer to a two component system, in which one monomer is designated A
and the other B.
Statistical Copolymers
Also called random copolymers. Here the monomeric units are distributed
randomly, and sometimes unevenly, in the polymer
chain: ~ABBAAABAABBBABAABA~.
Alternating Copolymers
Here the monomeric units are distributed in a regular periodic fashion, with nearly
equimolar amounts of each in the chain: ~ABABABABABABABAB~.
Block Copolymers
Instead of a mixed distribution of monomeric units, a long sequence or block of one
monomer is joined to a block of the second monomer:
~AAAAA-BBBBBBB~AAAAAAA~BBB~.
Graft Copolymers
As the name suggests, side chains of a given monomer are attached to the main
chain of the second monomer: ~AAAAAAA(BBBBBBB~)AAAAAAA(BBBB~)AAA~.
Polymer Properties
While they all contain molecules with very long chains, there are some important differences
between the properties of different types of polymers. Most polymers are formed into the desired shapes
after softening or melting by heating. Some, like the familiar polyethylene and polystyrene, may be melted
and reshaped again and again. These are called thermoplastic polymers. Many of these polymers are
recycled.
Thermosetting polymers char or burn when reheated. Examples include Bakelite and vulcanized rubber. Due
to the fact that these polymers can not be reheated, it makes it much more difficult to recycle them.
The major problem with recycling plastics is that they must be sorted by polymer composition. If the
polymers were just mixed, called commingled plastic, they would not be able to be shaped into
useable objects. The reason for this is the physical properties such as the melting point would be
too variable in commingled plastic.
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Plastic Recycling
Over the past few decades, the use of polymers in disposable consumer goods has grown tremendously. This
growth is proving to be taxing on the waste disposal system, consuming a large fraction of available landfill
space. Furthermore, the raw materials for these polymers are obtained from petroleum, a limited, nonrenewable resource. To reduce the demand for landfill space and the consumption of limited petroleum
reserves, the recycling of polymers has become a subject of concern. One of the problems faced in
recycling polymers is the great variety of polymers in use. To help sort wastes by type of polymer, most
disposable polymeric goods are labeled with a recycling code: three arrows around a number above the
polymer's acronym. These are intended to help consumers separate the waste polymers according to type
before disposing of them.
What can be Recycled?
Do NOT Recycle This Plastic
1. Automotive Product
Plastic Code Number
Recyclable Containers
Soda Bottles
Water Bottles
Juice Bottles
Cooking Oil Bottles
Soap/Detergent Bottles
Shampoo Bottles
Clear Liquor Bottles
Food Jars (Peanut Butter etc.)
Degradable Polymers
Plastic Code Number
Containers Including:
Recyclable Containers
Motor Oil Bottles
Milk Bottles
Gasoline and Oil Additive
Water Bottles
Juice Bottles
Cooking Oil Containers
Washer Fluid Bottles
Shampoo Bottles
Anti-Freeze Containers
Bottles
2. Brown Liquor Bottles
3. All Containers Marked With
The Following Codes:
Butter/Margarine Tubs
Cottage Cheese Containers
Ice Cream Containers
Baby Wipe Containers
Code
Polymer
Degradation of polymers can be accomplished by
microorganisms or by photodegradation. Many polymers are
1 PETE
polyethylene terphthalate
made to degrade more readily by the addition of additives.
2 HDPE
high density polyethylene
Thermosetting polymers are an important target for these
3 V (PVC)
polyvinyl chloride
additives because they cannot be recycled. Photodegradable
4 LDPE
low density polyethylene
plastics can have an additive that is sensitive to ultraviolet
5 PP
polypropylene
light. Biodegradable plastics can have starch or cellulose
6 PS
polystyrene
incorporated into the resin at the time of manufacture.
Microorganisms would consume the starch or cellulose and
7 OTHER all other
the plastic would be broken down into small pieces.
Photodegradation depends on light and oxygen, both of which are excluded in landfills. Biodegradation
depends on moisture and that also is limited in landfills. Newspapers have been found in landfills relatively
unchanged after 20 years.
.
74
POLYMERS
Down
1. This is another name
for Styrofoam.
2. A milky white polymer
from rubber trees.
3. This refers to the break down of
polymer with light and oxygen.
4. These are a large and varied group
of synthetic materials, which are processed
by forming or molding into shape.
6. This polymer make up Spandex.
7. If all atoms in the monomers are
incorporated into the polymer, the polymer
is called a(n) ________ polymer.
9. Milk contains this biopolymer.
11. In this type of copolymer the monomeric
units are distributed in a regular periodic
fashion.
12. This is the abbreviation for the polymer
designated by Plastic Code Number 1.
13. Latex heated with sulfur to make bridges
between the long chain polymers in rubber.
15. This class of polymers can be elastically
deformed a large amount when a force is
applied to them and can return to their
original shape when the force is released.
22. This type of copolymer is also called a
random copolymer.
Across
4. Common name of HDPE and LDPE that has the monomer
CH2=CH2.
5. Polymers that make up living organisms such as amino
acids, nucleic acids, and starch.
8. ~AAAAA-BBBBBBB~AAAAAAA~BBB~ is an example of
this type of copolymer.
10. These are the “units” that are chained together to
form polymers.(plural)
14. This category of polymers cannot be recycled because
they just decompose if they are heated.
16. Trees secrete this resin which is used to make lacquer
and shellac.
17. This polymer can form Fossilized tree sap.
18. This category of polymers may be melted and reshaped
again and again.
19. This organism eats mulberry leaves and produces a
polymer.
20. If some of the atoms of the monomers are released
into small molecules, such as water, the polymer is called
a(n) ________ polymer.
21. Dead wood and pulp from pine trees contain this
75
polymer that can be used to improve grip.
76
Name: __________________________________________
Polymer Activity
We are going to investigate two types of polymers in this activity. There are many types of polymers – all with unique
properties.
Flubber
Borate Solution:
1.
2.
3.
4.
5.
Put 85 ml of warm water into 100/150 ml beaker
Add 2.5 grams of powdered Borax
Add 3 drops of food coloring
Stir with a wooden stick
Describe this solution:
Glue Solution:
1.
2.
3.
4.
Put 115 grams of white glue into the Rubber Maid Bowl provided
Quickly add 90 ml of warm water to the bowl.
Stir with a wooden stick
Describe this solution:
Pour the Borate solution into the Rubber Maid bowl containing the Glue Solution. Mix together using a wooden stick.
When it is too thick to stir, use your hands to mix it. When most of the liquid is gone remove the Flubber from the bowl.
Let any excess liquid drip off onto paper towels. Enjoy!!
List 5 properties of this polymer:
a.
b.
c.
d.
e.
77
Guar Gum Polymer “Slime”
1.
2.
3.
4.
5.
6.
7.
Add 100 ml of distilled water to a plastic cup
Add 1 drop of food coloring and stir
Slowly and with constant stirring, add .75 grams of guar gum.
YOU DO NOT WANT LARGE CLUMPS TO FORM
Stir for 2 minutes – the solution will thicken slightly
Add 5 ml of .1M sodium borate solution.
Stir until the polymer gels.
8. List 5 properties of this polymer:
a.
b.
c.
d.
e.
78
Name ___________________________________________________________
Model Review
Draw and name each of the models:
#1
#2
Name
Name
#3
#4
Name
Name
#5
#6
Name
Name
79
#7
#8
Name
Name
#9
#10
Name
Name
#11
#12
Name
Name
80
Name ___________________________________________________________
Model Review
Draw and name each of the models:
#1
#2
Name
Name
#3
#4
Name
Name
#5
#6
Name
Name
81
#7
#8
Name
Name
#9
#10
Name
Name
#11
#12
Name
Name
82