Honors Chemistry
Unit 7B
Organic Chemistry continued
 Alcohols and Ethers
 Aldehydes, Ketones and carboxylic acids
 Esters
 Amines
1
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:
2
Ethers:

Organic compounds

General Formula:
- R and R’
 Naming:
o–
o–
o–
Examples:
3
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 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)
/ 2.5
_______________ Total points for Alcohols and Ethers
4
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
5
6
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
7
Ketones:
 Organic compound
 General Form:
O

R – C – R’
 Naming:
Example:
O

C–C-C
2-propanone
8
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
Example:
HOOC-C-C-COOH 1,4-butanedioic acid
9
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. 2 - propanone (acetone)
_______________ 2. 2-methylpropanal
_______________ 3. 2,2-dimethylpentanal
_______________ 4. methanal (formaldehyde)
_______________ 5. 2-pentanone
/ 2.5
_______________
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)
10
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
/ 2.5
_______________ 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)
11
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
12
13
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)
14
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
15
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
16
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)
17
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
18
19
Organic Compounds
Family
Functional Group
Ending
Naming
Alkane
Alkene
Alkyne
Aromatic
Alkyl halides
Alcohol
20
Family
Functional Group
Ending
Naming
Ether
Aldehyde
Ketone
Carboxylic Acid
Ester
Amine
21
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
22
23
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
24
25
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
26
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
27
28
29
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.
30
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.
31
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.
32
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.
.
33
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
34
polymer that can be used to improve grip.
35
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.
36
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.
37
Name ___________________________________________________________
Model Review
Draw and name each of the models:
#1
#2
Name
Name
#3
#4
Name
Name
#5
#6
Name
Name
38
#7
#8
Name
Name
#9
#10
Name
Name
#11
#12
Name
Name
39
Name ___________________________________________________________
Model Review
Draw and name each of the models:
#1
#2
Name
Name
#3
#4
Name
Name
#5
#6
Name
Name
40
#7
#8
Name
Name
#9
#10
Name
Name
#11
#12
Name
Name
41