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Organic Chemistry : Ch. 19

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Title: Organic Chemistry : Ch. 19


1
Organic 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.

2
Carbon 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.

3
Story 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.

4
Story 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)
5
Story 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
6
Story 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.

7
Story 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.)

8
Hydrocarbons
  • Hydrocarbons are a class of organic compounds
    which contain only carbon and hydrogen.
  • Hydrocarbons are characterized as carbon chains,
    branched chains, and rings.

9
Hydrocarbons
  • 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/

10
Journal 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

11
Hydrocarbons 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
12
Journal Activity 2
  • In your journal fill in the data table below for
    the alkenes ( ethene octene)
  • Name Structural Formula Molecular Formula Uses

13
Alkynes
  • Alkynes are hydrocarbons which contain a triple
    bond between carbons.
  • Alkynes end in yne.
  • Ethyne, Propyne, Butyne, etc.

14
Journal Activity 3
  • Diagram the following hydrocarbons
  • Propene b) Butyne
  • c) 2 hexene d) 2 - octyne

15
Journal 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.

16
Branched 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.

17
Journal 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

18
Branched 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
19
Isomers
  • 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)

20
Journal Activity 6
  • Diagram a pentane molecule, and two isomers of
    this molecule. Name each isomer.

21
Aromatic 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.

22
Journal Activity 7
  • Diagram the following cyclic hydrocarbons and
    give the molecular formula of each.
  • Cyclopentane b) cyclobutene
  • c) Benzene d) cyclohexane

23
Benzene
  • 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.

24
Journal 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).

25
Hydrocarbon 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

26
Hydrocarbon 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.

27
Organic 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.

28
Organic Compounds
  • The organic compounds we will study include
  • Alcohols sugars
  • Aldehydes starches
  • Amines lipids
  • Carboxylic Acids (Organic Acids)
  • Esters proteins
  • Ethers
  • Ketones

29
Alcohols
  • 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)
30
Alcohol 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.

31
Types 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.

32
Alcohol Types
  • Diagram a primary alcohol below ( ethanol)
  • Diagram a secondary alcohol below (2 butanol)
  • Diagram a tertiary alcohol below
    2-methyl-2-propanol

33
Naming 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.

34
Diols/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.

35
Naming and Classifying Alcohols
  • Draw the structural formula for the following
    alcohols and classify them
  • 3-hexanol b) methanol
  • c) 1,2,3-propanetriol (glycerol)

36
Alcohol 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.

37
Alcohol 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.

38
Helpful Websites for Alcohols
  • http//dl.clackamas.cc.or.us/ch106-03/nomencla.htm
  • http//jchemed.chem.wisc.edu/JCESoft/CCA/CCA5/MAIN
    /HOME.HTM

39
Halocarbons
  • 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.

40
Halocarbon 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
41
PCBs
  • 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.

42
Naming Halocarbons
  • Draw the structure for the following
  • Trichloromethane (chloroform)
  • b) Tetraiodomethane c) 2-fluoro pentane

43
Ethers
  • 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.

44
Naming Ethers
  • Draw the structural diagram for the following
  • Dimethyl ether b) methoxypentane
  • c) Diethyl ether d) Diphenyl ether

45
Aldehydes
  • 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

46
Uses 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.

47
Ketones
  • 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.

48
Organic 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.

49
Naming Organic Acids
  • Draw the structure for the following organic
    acids
  • Methanoic acid b) Ethanoic acid
  • c) Butanoic acid d) Propanoic acid

50
Properties 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)

51
Esters
  • 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.

52
Esters
  • Diagram the reaction of ethanoic acid with
    methanol. Name the ester which forms.

53
Esters
  • Draw the structural formula for the following
    esters
  • a) Ethyl butanoate b) pentyl ethanoate

54
Amines
  • 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.

55
Amines
  • 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.

56
Amines
  • 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
57
Naming Amines
  • Draw the structure for the following amines.
  • a) Butanamine b) pentylamine

58
Amides
  • 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.

59
Amides
  • Amides are found in biological compounds and in
    some synthetic polymers such as nylon.

Nylon a polymer with an amide group in the
chain.
60
Naming Amides
  • Draw the structure of ethanamide.

What is the name of the amide above?
61
Organic 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

62
Polymers
  • 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)

63
Polymers
  • 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
64
Polymers
  • Other polymers include
  • Teflon
  • Polystyrene
  • Proteins
  • Lipids
  • Starches

Polytetrafluoroethene teflon monomer
65
Polymers
  • 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.
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