Download Carboxylic Acids

Organic Chemistry
Organic chemistry is the study of carbon compounds, their properties and their
interactions. ( except CO2 , CO , CO32-, CN-)
A) Sources:
i) living organisms - plants , animals, etc
ii) non-living material ( coal, oil , wood, natural gas)
B) Classification of Organic Compounds
Organic Compounds
Hydrocarbons
Aliphatic
Carbohydrates
Alcohols
Aromatic
Ketones
Carboxylic
acids Aldehydes
Alkanes
Alkenes
Alkynes
C)Bonding: covalent bonding with carbon as the main player
Carbon Hybrid
C
1s 2 2s1 2p1 2p1 2p 1
(sp3 hybrid)
Hydrocarbons- Compounds composed of carbon and hydrogen atoms
1) Alkanes: hydrocarbons with the general formula C nH2n+2
-saturated hydrocarbon ( all single covalent bonds- paraffins ) ending in "ane"
Homologous Series of Alkanes
Name
Molecula Properties ( MP, BP, State )
r
Formula
condensed structural formula
#
isomers
methane
CH4
MP = -182.48oC
BP= -164oC
CH4
1
ethane
C2H6
MP = -183.3oC
BP= -88.63oC
CH3CH3
1
propane
MP = -189.69oC
BP= -42.07oC
CH3CH2CH3
1
butane
MP = -138.35oC
BP= -0.5oC
CH3(CH2)2CH3
2
pentane
MP = -129.72oC
BP= 36.07oC
CH3(CH2)3CH3
3
hexane
MP = -95oC
BP= 68.95oC
CH3(CH2)4CH3
5
heptane
MP = -90.61oC
BP=98.42oC
9
octane
MP = -56.79oC
BP= 125.66oC
18
nonane
MP = -51oC
BP= 150.79oC
35
decane
undecane
dodecane
tridecane
The trend in boiling point is due to _________________________________________
Isomers:
different structure forms of the same molecule and therefore different properties
Examples of isomers for butane: (2)
n-butane
2-methylpropane
H H H H
H C C C C H
H H H H
H H H
H C C C H
H
H
H C H
H
Rules for naming alkanes;
1.
2.
3.
4.
5.
6.
Select the longest carbon chain. ( parent chain )
Identify the attached ( branched ) alkyl groups: CH3- methyl ,CH3CH2- ethyl, CH3CH2CH2- propyl
Identify halogens: fluoro , chloro , bromo , iodo
Number the carbon chain form the end that yields the lowest total of the numerical coefficients (
check numbering from both directions )
Name the attached groups in alphabetical order: chloro, ethyl, methyl . Use the prefix (di, tri, tetra )
to indicate the total number of groups )
Number the position on the carbon chain that the branched group is attached
Commas are used to separate location of groups and hyphens are used to separate numbers from
words.
( nothing between names )
Drawing and Naming Isomers
A) Isomers for Pentane (3)
B) Isomers of Hexane ( 5)
C) Isomers of Heptene ( 9 )
Practice Naming Alkanes
C C
C
C C
C
C
Write the name for each of the following
C
CH3CH3
C
C C
Br
C
C
C
C
C
C
C C
C C C
C
C
C
C C
C C
C
C C
C
I
C
C
C
C
C
C C C
C C C
C
C
C
C
C
C
C
C C C C
C
C
Br
C
C C
C C
I
C
C
C C C C
C
C C C C
Draw the skeletal formula for each of the following ( and write the molecular formula )
3-ethyl-3-methylhexane
n-tridecane
5-(2-methylpropyl)decane
3-ethylheptane
2,2,3-trimethyloctane
5-butyl-3-ethyl-6-methylundecane
3-chlorododecane
1-iodo-3-propyloctane
3-ethyl-2-methyl-4-propyldecane
4-propylnonane
2,3,4-trimethylpentane
C
Reactions of Alkanes (write balanced equations for each reaction )
1.
Combustion ( react with oxygen )
A) Complete combustion - produce water and carbon dioxide
C3H8 + O2 
C6H14 + O2 
B) Incomplete combustion - produce carbon , carbon monoxide, CO2 , H2O
C2H6 + O2 
C2H6 + O2 
2.
C
+ CO2 +
CO +
CO2
H 2O
+
H2 O
Substitution ( replacing hydrogen with another atom )
this is difficult because the C-H bond is very strong and therefore requires large
amounts of energy to break a hydrogen free.
CH3CH2CH3 + HBr 
3.
CH3CHBrCH3
+
H2
Alkanes are not reactive with acids or bases or chemicals that steal electrons. (
oxidizing agents )
Alkenes (unsaturated hydrocarbons)
-the presence of C=C (double) bonds results in less hydrogens bonded to the carbons
-functional group
C=C
general formula CnH2n
-this group tends to lower the FOA for other molecules
Name
Skeletal formula, Structural
and Molecular Formula
Properties ( MP, BP, State )
ethene
MP= -169.15oC
BP = -103.71oC
propene
( 1-propene )
MP = -185.25oC
BP = -47.4oC
1-butene
MP = -185.35oC BP = -6.3oC
2-butene (cis)
MP = -139.91oC
BP = 3.7oC
MP = -105.55oC
BP = 0.88oC
C5H10
MP =
BP = 121.5oC
C8H16
MP = -101.73oC
BP = 121.3oC
H
H
C=C
H
H
C2H4
2-butene (trans)
Naming Alkenes:
1.Select the longest C-chain containing the double bond.
2.Number the spaces between the carbon atoms so that the double bond is at the lowest possible number.
3. Name the branches as with alkanes. State the numbered space where the double bond appears in front of the
alkene name.
Two double Bonds
The location of both double bonds must be indicated and the suffix is changed to "diene ".
1,2-butadiene
1,3-butadiene
1,3,5,7-octatetrene ( Multiple Double Bonds )
C
C C C
C C
C C
C
C C C
C C
C C
Draw the skeletal ( structural ) formulae for each of the following:
1-pentene
2-hexene
3-methyl-2-pentene
3-ethyl-5-methyl-2,4-hexadiene
2,5-dimethyl-3-nonene
6-chloro-3-ethyl-1-heptene
Name the following :
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C C
C
Draw and name the 5 isomers of C5H10 which are alkenes:
C
C
C
Alkenes: Some Uses and Types of Reaction
Uses: Ethene is used as a bleach, an anesthetic, a fruit colouring agent ( causes ripening of fruit in sealed
box) , production of antifreeze, ethanol (alcohol) , ether , medicines and plastics
Polythene ( polyethylene ) is joined units of ethene that make garbage bags and zip lock bags
Alkene Reactions
1.
Addition Type:
a. Additions of Compounds will follow Markownikoff’s Rule ( The positive part of the
reagent that attacks the alkene across the double bond will bond onto the “C” at the
double bond that has the most “H” atoms already bonded.
Ex : CH3CH2CH=CH2 + HBr

CH2CH2 + HCl

propene + hydrogen chloride 
b. Halogenations: reaction of halogen across the double bond
Ex.
CH3CH=CH2 + Br2 
2-methyl-2-butene + bromine 
Since Br2 becomes decolourized by this reaction it can be used as a test for saturation.
Demo:
cyclohexane + Br2 
cyclohexene + Br2 
c. Hydrogenation: reaction of hydrogen across the double bond
Ex.
CH2CH2 + H2 (Pt catalyst) 
2-methyl-2-butene + hydrogen
Pt


This reaction is used for converting unsaturated hydrocarbons into saturated
hydrocarbons
unsaturated (liquids or oils ) + hydrogen  saturated (solids or fats)
Liver converts saturated into cholesterol. Unsaturated reverse cholesterol build up
d. Oxidations : [O] -atomic uncombined oxygen comes from KMnO4 , K2CrO4 , K2Cr2O7
and other solutions. The simplified reaction is:
O
H
H
H
H
H [O]
H
H2O
C
C
H
C
C
C
C
H
H
H
H
H
OH OH
1,2-ethonediol
Unstable
(ethylene glycol)
3-methyl-1-butene + [O]  epoxy
+ H 2O 
1-butene + [O] 
+ H2O 
e. Hydrolysis: a reaction that involves adding water across the double bond
C
C
+
H2SO4
C
C
catalyst
H
OH
H - OH
4-methyl-2-pentene + H2O 
ethanol
Alkyne Verification Experiment
Purpose: to produce an alkyne and to observe both its chemical and its physical properties
Apparatus: test tubes, stoppers, pneumatic trough, splints, Bunsen burner
Method:
1. Fill the pneumatic trough with water to the overflow line. Submerge 4 test tubes in the water.
2. Add a piece of calcium carbide (CaC2) to the water and collect the ethyne (acetylene ) gas by the
downward displacement of water. Collect 3 full test tubes of the ethyne and one test tube that is 1/12
full of ethyne. Observe
3. To one of the full test tubes , add a small amount of bromine water, shake and observe.
4. To the second full test tube add KMnO4 (aq) , shake and observe.
5. Conduct an ignition test on the two remaining test tubes. Observe
Observations:
Reactant description:
CaC2
H2 O
Product Description
C 2 H2
Ca(OH)2
Reaction Descriptions:
A) Bromine water:
B) Potassium permanganate solution
C) Ignition test
full: 1/12 full:
Conclusions:
1. Write a balanced equation for the production of ethyne.
2. Write formula equations (4) for each of the ethyne reactions. Explain the purpose of each of the
reactions.
3. Explain the intramolecular and the intermolecular bonding that occurs in ethyne.
4. Draw and name the isomers of C5H8 ( some may not be alkynes)
5. Construct a model of an acetylene lamp that could have been used as a lantern for early automobiles.
Explain how your model works to make the light and direct the light down the road.
6. Write the formula equations for each of the following: A) hydrogenation of ethyne, B) hydrolysis of
ethyne , C) chlorination of propyne, D) bromination of 2-pentyne.
7. Explain the method you would use to identify the contents of three vials, containing propane,
propene, and propyne.
8. Calculate the volume of ethyne produced at 27.0oC and 95.0kPa, when 20.0g of calcium carbide reacts
with excess water. Calculate the volume of air (21% O2) required for the complete combustion of the
ethyne.
Reactions of Alcohols
Type 1 Oxidation (gentle)
A strong oxidizer (source of [O] ) is necessary for the reaction with different types of alcohols.
A) Oxidation of a Primary alcohol ( 1-butanol )
Write the structural equation for 1-butanol with [O] from KMnO4(aq)
+ [O] 
KMnO4(aq)
Note:
1-butanol (an alcohol ) was oxidized to 1-butanal ( an aldehyde.
-atomic oxygen [O] takes the H from the OH group and a second H from the
carbon that holds the OH group
B) Oxidation of a Secondary Alcohol ( 2-butanol , sec. butyl alcohol )
Write the structural equation for the reaction with KMnO4
2-butanol was oxidized to ________________ ( ______________________)
C) Oxidation of a Tertiary Alcohol 2-methyl-2-propanol
Write the structural equation for the reaction with KMnO4
Tertiary alcohols do_______react because _____________________________
Type 2 Strong Oxidations
An aldehyde made by gentle oxidation is reacted with another [O]
ethanal + [O] ---> ethanoic acid
Summary:
Primary alcohols + [O]
Secondary alcohols + [O]
Tertiary alcohols + [O] 
Aldehyde + [O]

 ____________ + _____________
____________ + ______________
Alcohol Worksheet
Draw the following and indicate whether they are primary, secondary, or tertiary.
Alcohols are named by numbering the longest chain containing the OH group from the end that will
give the position of the alcohol group the lowest possible number. An "ol" ending indicates an
alcohol.
3-methyl-2-pentanol
2-methyl-2-butanol
1.
2,5,5-trimethyl-1-hexanol
2. A)
B)
3.
4-methyl-2-pentanol
Why is methanol called "wood alcohol" and ethanol called "grain alcohol"?
List the physical properties of methanol and ethanol.
formula, MP , BP, density, colour, odour, state
Explain using bonding concepts which should have the lower boiling point:
A) 1-butanol or 1-chlorobutane
B) 1-butanol or 2-butanol
4. Write structural equations for the following: [O] source KMnO 4(aq)
A)
ethanol + [O] 
B)
2-propanol + [O] 
C)
1-propanol + [O] 
D) 3-pentanol + [O] 
E)
2-methyl-2-propanol + [O] --->
F)
____________ + [O]  pentanal + water
G) ___________ + [O]  butanone + water
H) ethanol + [O] acidified K2CrO4  ________ + H2O
Cr3+(aq)
yellow colour
pale green colour
Explain how this reaction could be used in a breathalyzer.
Substance
Aldehydes and Ketones
Functional Group
General Formula
Aldehyde
Ketone
1.
2.
Draw the structural formulae for each of the following
2-methyl-3-pentanone
2-methyl-3-ethylhexanal
4,5-dimethyl-2-hexanone
4-methyl-2-bromopentanal
Write the structural equations for the preparation of:
A) 2,3-dimethylbutanal
B) 5,5,8-trimethyl-4-nonone
C) Ethanal, starting with calcium carbide. Use 4 separate equations to achieve this final substance)
3.
Complete this oxidation reaction equation:
Copper oxide + 2-propanol 
4.
+
Draw 4 isomers of C4H8O ( aldehydes and ketones )
+
Carboxylic Acids
substances made by the oxidation of an ____________________
Functional Group
General Formula
Molecular formula
Structural Formula
carboxylic acid
Name
methanoic acid
ethanoic acid
(acetic acid )
propanoic acid
Esters
Compounds derived from a reaction between a carboxylic acid and an alcohol.
Functional Group
General Formula
Ester linkage (key)
Production: alcohol + carboxylic acid  ester + water
O
O
C OH
+ C C
C O C C
+ H2O
HO
Complete the following as structural equations:
1. propanol + ethanoic acid 
2.
propanoic acid + ethanol 
List (A) Characteristics of esters.
(B) Uses of Ester ( include specific flavours )
Amines, Amino acids, Amides ( peptides ) & Polyamides
Amines:
1. Production
CH3CH2I +
2NH3  CH3CH2NH2 + NH4I
ethyl iodide + ammonia  ethylamine + ammonium iodide
2. General formula and functional group:
Names and Structural Formulae
methylamine
1propylamine
R-NH2
-NH2
3.
4. Uses: dyes ( congo red and methyl orange )
1-octylamine
plastics ( Melmac- melamine )
5. Primary amine occurs when _________________________________
Secondary amine occurs when______________________________
Tertiary amine occurs when _________________________________
Amino Acids - amine links to a carboxylic acid
1. Amino acid formation:
glycine
alanine
H
O
N-C-C-O-H
H
H
O
H-C-C-C-O-H
H
H N H
2.
Amino acids are essential both in plants and animals ( usually for synesizing
polyamides (polypeptides) called Proteins.
eg. skin, hair, muscles nails etc
3. Amine + acid  amide (peptide) linkage + water
H
O
O
H
H2O
-C-C-N
-C-C-N-C-C-C- +
+
C-C-CH
H
O
4. Condensation Polymerization- of AMINO ACID monomers
4
H
O
H
C-C-N
H
O
+
H2O