Title: Organic Chemistry : Ch. 19
1Organic Chemistry Ch. 19
- Organic chemistry is the branch of chemistry
which deals with carbon based compounds. - Carbon is an element which has the unique ability
to bond long chains, rings, and react with other
elements to form a variety of compounds.
2Carbon Compounds
- Carbon compounds are found in many forms gases,
aqueous, and solids. - Carbon is recycled in nature by the carbon cycle.
- Carbon chains can be modified by reactions to
form different type of carbon based (organic)
compounds.
3Story of Carbon
- Carbon is a major component of living things.
- Lipids (fats and oils), sugars, starches,
proteins, DNA, etc. are composed of carbon,
hydrogen, oxygen, nitrogen, and other atoms. - Lipids, sugars, and starches are composed of
carbon, hydrogen, and oxygen. - Proteins are composed of carbon, hydrogen,
oxygen, nitrogen, and sometimes sulfur.
4Story of Carbon
- When organisms die and decompose in a low oxygen
environment, these carbon compounds(with the aide
of anaerobic bacteria) will break off the oxygen,
nitrogen, and other atoms bonded to the compounds.
Animal Fat (one molecule)
5Story of Carbon
- When the oxygen, nitrogen, sulfur, and other
atoms are removed by bacteria, what is left is a
hydrocarbon ( Carbon and hydrogen only) - These hydrocarbons are of mixed sizes, and are
known as crude oil when recovered from the
earth.
Hydrocarbons C H atoms
6Story of Carbon
- Carbon atoms have four electrons in their outer
energy level, and will want to covalently bond
(share electrons) with itself and other atoms to
form more stable chain and ring compounds. - The crude oil contains a mixture of hydrocarbons
including butane(lighter fluid), gasoline,
diesel, candle wax, etc.
7Story of Carbon
- The hydrocarbons found in crude oil can be
separated based upon their boiling points and
refined or distilled. - By adding substances to them a host of other
organic compounds can be produced (alcohols,
esters, ethers, plastic, styrofoam, etc.)
8Hydrocarbons
- Hydrocarbons are a class of organic compounds
which contain only carbon and hydrogen. - Hydrocarbons are characterized as carbon chains,
branched chains, and rings.
9Hydrocarbons
- Carbon has 4 valence electrons and will form 4
covalent bonds with hydrogen. A line between
carbon and another atom represents the sharing of
2 electrons. Therefore every carbon in an
organic compound needs 4 lines around it. - Hydrocarbons with all single carbon bonds are
described as the Alkanes. - http//www.nyu.edu/pages/mathmol/library/hydrocarb
ons/
10Journal Activity 1
- In your journal prepare a data table which shows
the following Fill in the information for
methane through decane. Use the website given to
find the uses for. - Alkane Name Structural Formula Molecular
Formula Uses For
11Hydrocarbons Alkenes
- Carbon atoms have the ability to bond with other
atoms with single, double, or even triple bonds. - When carbon bonds to another carbon with a double
bond, and only carbon and hydrogen atoms are in a
compound its termed an alkene. - Ethylene(ethene) is the simplest alkene.
http//users.rcn.com/jkimball.ma.ultranet/BiologyP
ages/E/Ethylene.html
12Journal Activity 2
- In your journal fill in the data table below for
the alkenes ( ethene octene) - Name Structural Formula Molecular Formula Uses
13Alkynes
- Alkynes are hydrocarbons which contain a triple
bond between carbons. - Alkynes end in yne.
- Ethyne, Propyne, Butyne, etc.
14Journal Activity 3
- Diagram the following hydrocarbons
- Propene b) Butyne
- c) 2 hexene d) 2 - octyne
15Journal Activity 4
- http//www.ausetute.com.au/ethene.html
- Using the website above to answer the questions
below in regards to ethene or ethylene. - Explain how ethene can be made into ethanol.
- Explain how ethene can be made into ethylene
glycol (antifreeze). - What is ethene extracted from?
- Describe one other chemical which can be produced
from ethyene.
16Branched Hydrocarbons
- Hydrocarbons come in a variety of forms.
- Not all hydrocarbons are linear, some are
branched and some are cyclic. - Branched hydrocarbons have a carbon backbone
with groups attached to this backbone. - To name these compounds you need to follow the
basic rules below (IUPAC) - Find the longest carbon chain (backbone) and
write its corresponding name. - Identify the groups attached to this chain.
- Assign the carbons in the chain numbers, which
make the group have the lowest number. - Identify any double or triple bonds with the
corresponding carbon number.
17Journal Activity 5
- Diagram the following branched hydrocarbons
- 2 methyl, hexane b) 2,2, dimethyl pentane
- c) 2,3 dimethyl octane d) 2,4 dimethyl 3-decene
18Branched Hydrocarbons
- Branched hydrocarbons are found in crude oil and
can also by synthesized by chemical reactions. - Hydrocarbons with only single bonds are termed
saturated hydrocarbons. - Hydrocarbons with a double or triple bond are
called unsaturated hydrocarbons.
Saturated hydrocarbon Pentane
19Isomers
- Diagram the following hydrocarbons
- Butane b) 2-methyl propane
- The molecular formula for both of these is C4H10
- Even though the formula is the same the
properties of these compounds is very different. - This is an example of isomers. Isomers are
compounds with the same formula but different
chemical and physical properties. (Boiling point,
etc)
20Journal Activity 6
- Diagram a pentane molecule, and two isomers of
this molecule. Name each isomer.
21Aromatic Hydrocarbons
- Hydrocarbons can also form ring structures.
- The simplest would be cyclopropane, cyclobutane,
and cyclopentane. - When six carbons form a ring we enter a new class
of hydrocarbons called aromatic hydrocarbons. - Benzene is the first member of aromatic
hydrocarbons.
22Journal Activity 7
- Diagram the following cyclic hydrocarbons and
give the molecular formula of each. - Cyclopentane b) cyclobutene
- c) Benzene d) cyclohexane
23Benzene
- Benzene is a member of the aromatic (ring)
hydrocarbons. - These hydrocarbons have a variety of uses as
pesticides, flavorings, and a host of other uses.
24Journal Activity 8
- http//www.uyseg.org/greener_industry/pages/benzen
e/2BenzeneUses.htm - Use the website above to describe how benzene
is used to produce styrene, nylon rope,
dynamite (TNT), and 2,4 D( weed killer).
25Hydrocarbon Summary
- At this point weve concluded our study of
hydrocarbons. Below is a summary of the
hydrocarbon compounds weve studied - Alkanes
- Alkenes
- Alkynes
- Branched alkanes, alkenes, alkynes
- Cyclic hydrocarbons
- Aromatic hydrocarbons
26Hydrocarbon Tutorial Websites
- http//chemed.chem.purdue.edu/genchem/topicreview/
bp/1organic/organic.html - Provides a good overview of hydrocarbons with
naming practice. - http//www.ausetute.com.au/namsanes.html
- Great web-site for all concepts of chemistry.
Choose a tutorial from the drop down on alkanes,
alkenes, etc.
27Organic Compounds
- Hydrocarbons are used to synthesize a large
amount of different organic compounds. - In addition some of these organic compounds are
naturally produced in living things. - By adding substances and breaking bonds the
hydrocarbon can become a new class of organic
compound.
28Organic Compounds
- The organic compounds we will study include
- Alcohols sugars
- Aldehydes starches
- Amines lipids
- Carboxylic Acids (Organic Acids)
- Esters proteins
- Ethers
- Ketones
29Alcohols
- Alcohols can be produced 3 different ways.
Alcohols are compounds with an OH functional
group (Hydroxyl) on a carbon skeleton. - C - C
- OH
Hydroxyl Group (Alcohol)
30Alcohol Properties
- Alcohols with up to 4 carbon atoms are soluble in
water as a result of the OH group on the carbon
chain. - As more carbon atoms are added to the chain the
solubility decreases. - Alcohols have higher boiling points than do the
hydrocarbons from which they are formed from.
31Types of Alcohols
- There are three types of alcohols Primary,
Secondary, and tertiary. These types of alcohols
are determined by where the OH is on the carbon
chain. - Primary OH is at the end of a carbon chain.
- Secondary OH is in the middle, with 2 C atoms
attached to the C with the OH. - Tertiary OH is in the middle with 3 C atoms
attached to the C with the OH.
32Alcohol Types
- Diagram a primary alcohol below ( ethanol)
- Diagram a secondary alcohol below (2 butanol)
- Diagram a tertiary alcohol below
2-methyl-2-propanol
33Naming Alcohols
- Alcohols are named by finding their hydrocarbon
skeleton and ending this with ol. - The OH group is identified to which carbon in the
chain it is attached to. - Name the following alcohol and identify it as
primary, secondary, or tertiary. -
34Diols/Triols
- Alcohols can have more than one OH group on a
hydrocarbon chain. - Alcohols with two OHs are called diols, and the
prefix di is added before the ol in naming. - Alcohols with three OHs are called triols, and
the prefix tri is added before the ol in
naming. - Write the structural formula for 1,2-ethanediol.
This is also known as ethylene glycol or
antifreeze.
35Naming and Classifying Alcohols
- Draw the structural formula for the following
alcohols and classify them - 3-hexanol b) methanol
- c) 1,2,3-propanetriol (glycerol)
36Alcohol Formation
- Alcohols can be produced three ways
- 1) From using bacteria or yeast in the process of
fermentation. (ethanol and carbon dioxide are
the waste products of yeast as they eat sugar)
12 - 2) Addition of water to an alkene. (with an acid
catalyst) - 3) Hydrolysis of a halocarbons.
37Alcohol Formation
- Diagram the formation of ethanol from ethene
water ( with an acid catalyst H2SO4) - Diagram the formation of ethanol from the
hydrolysis (splitting by water) of chloroethane.
38Helpful Websites for Alcohols
- http//dl.clackamas.cc.or.us/ch106-03/nomencla.htm
- http//jchemed.chem.wisc.edu/JCESoft/CCA/CCA5/MAIN
/HOME.HTM
39Halocarbons
- Halocarbons are organic compounds in which
halogens have replaced hydrogen. - Halocarbons are named as to where the halogens
are attached, and how many halogens there are. - The halogen prefix is used fluoro, chloro,
bromo, etc.
40Halocarbon Uses
- Halocarbons are used extensively as pesticides,
insecticides, dry cleaning, and other areas. - Many of the most toxic chemicals have been
halocarbons. - PCBs poly chlorinated biphenols, are toxic
synthesized halocarbons.
DDT a halocarbon which was banned in 1972
DDT 1,1,1-trichloro-2,2-bis(p-chlorophenyl)
ethane
41PCBs
- PCBs are halocarbons which contain two phenols
with chlorine on them. - PCBs have been shown to be accumulative in fatty
tissue, and bioaccumulate. - The biphenols typically can persist in soil for
15-25 years.
42Naming Halocarbons
- Draw the structure for the following
- Trichloromethane (chloroform)
- b) Tetraiodomethane c) 2-fluoro pentane
43Ethers
- Ethers are organic compounds which have an oxygen
atom bonded to two different carbons. - Ethers are named by naming the compound on each
side and ending in ether. Or by writing the
short version of each with oxy in the middle. - Ethers were used anesthetics, but safer gases
have been found. - Small ethers are soluble in water, but larger
ethers are insoluble. - Applications of ethers are solvents, gasoline
additive, etc.
44Naming Ethers
- Draw the structural diagram for the following
- Dimethyl ether b) methoxypentane
- c) Diethyl ether d) Diphenyl ether
45Aldehydes
- Aldehydes are organic compounds which have a
carbonyl group(CO) at the end of a carbon chain. - Aldehydes are named by ending the molecule with
an al. - Diagram ethanal, and propanal below
46Uses of Aldehydes
- Aldehydes are used as preservatives, flavorings,
perfumes, etc. - Vanilla flavoring and cinnamon are natural
aldehyde flavors. - Ethanol is converted to acetaldehyde (propanal)
in the human body.
47Ketones
- Ketones are a class of organic compounds with a
carbonyl group (CO) in the middle of a carbon
chain. (Ketones are never alone) - Propanone is the simplest ketone and is known as
acetone. Acetone is a top 50 industrial chemical. - Acetone is a common solvent for nonpolar
substances. (fingernail polish remover) - To name ketones end the carbon chain in one.
48Organic Acids (Carboxylic Acids)
- Carboxylic acids are a group of organic compounds
which have a (COOH) functional group. - Carboxylic or organic acids are weak acids.
- Examples are acetic acid, citric acid, benzoic
acid, etc. - To name these acids use the carbon chain root
and add the suffix oic and the word acid.
49Naming Organic Acids
- Draw the structure for the following organic
acids - Methanoic acid b) Ethanoic acid
- c) Butanoic acid d) Propanoic acid
50Properties of Organic Acids
- Methanoic acid (formic acid) is the acid in bee
and ant stings. - Ethanoic acid is acetic acid, found in vinegar
- Small chain organic acids are soluble in water.
- Lactic acid is an organic acid which builds up in
body cells. - Ascorbic acid (Vitamin C) is found in citrus
fruits and tomatoes. - Bacteria reacts butter into butanoic acid.
(rancid butter)
51Esters
- Esters are organic compounds formed when an
alcohol is added to an organic acid. - Esters have distinctive odors.
- Esters have the functional group (COOC)
- Esters are named by naming the alcohol name first
ending in yl, then the acid name is given
ending in oate. - When an ester is synthesized from an alcohol and
organic acid, the alcohol gives off the (O) atom
, and the acid gives two (H) atoms to form water.
52Esters
- Diagram the reaction of ethanoic acid with
methanol. Name the ester which forms.
53Esters
- Draw the structural formula for the following
esters - a) Ethyl butanoate b) pentyl ethanoate
54Amines
- An amine is an organic compound which contains an
amino functional group. - An amino functional group is NH2
- Amines can contain several amino functional
groups.
55Amines
- Amines are named by adding the suffix amine to
the root name of the hydrocarbon. - Amines are also named by naming the hydrocarbon
ending in yl with the suffix amine.
56Amines
- Amines are important biological compounds.
- Amino acids which make up proteins contain an
amino group along with an organic acid group. - Amines are found in DNA.
- Amines are the basis of several addictive drugs
nicotine, cocaine, and amphetamines.
Amino Group
Methamphetamine
57Naming Amines
- Draw the structure for the following amines.
- a) Butanamine b) pentylamine
58Amides
- Amides are produced when amines are added to an
organic acid. - Amides have an amino group and a carbonyl group
attached to an end carbon. - Amides are by adding the suffix amide to the
end of the hydrocarbon root.
59Amides
- Amides are found in biological compounds and in
some synthetic polymers such as nylon.
Nylon a polymer with an amide group in the
chain.
60Naming Amides
- Draw the structure of ethanamide.
What is the name of the amide above?
61Organic Compound Summary
- The following are the organic compounds weve
studied. They are identified by their
functional group. - Hydrocarbons Esters
- Alcohols Organic Acids
- Ethers Amines
- Ketones Amides
- Aldehydes Halocarbons
62Polymers
- Small organic molecules (monomers) can be reacted
to form long organic molecules (polymers) - Example of polymers are polyethylene (plastic),
polyvinylchloride (PVC), nylon, polyester, etc. - Polymers can be formed by a condensation reaction
(water is produced)
63Polymers
- Polymers can be formed by an elimination
reaction, where a simple molecule (water, etc.)
is removed and a new compound is formed.
PVC polyvinyl chloride polymer
64Polymers
- Other polymers include
- Teflon
- Polystyrene
- Proteins
- Lipids
- Starches
Polytetrafluoroethene teflon monomer
65Polymers
- Nylon is a polymer involving an amide monomer.
- Nylon was synthesiszed in the 1930s and named
after the cities of New York and London. - Nylon is produced by adding an organic acid to an
amine. - Nylon has many uses.