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/

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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
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Journal Activity 2

• In your journal fill in the data table below for
  the alkenes ( ethene octene)
• Name Structural Formula Molecular Formula Uses

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Alkynes

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

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Journal Activity 3

• Diagram the following hydrocarbons
• Propene b) Butyne
• c) 2 hexene d) 2 - octyne

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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.

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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

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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)

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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

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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.

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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.

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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)
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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.

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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.

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Alcohol Types

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

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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.

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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

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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.

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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

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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

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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.

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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.

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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
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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.

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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.
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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
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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.