chemistry 20 - sharpschoolcompositehighfmpsd.sharpschool.com/userfiles/servers... · web viewthe...

41
Chemistry 30 Organic Chemistry Notes A. Carbon Compounds 30-C1.1k define organic compounds as compounds containing carbon, recognizing inorganic exceptions such as carbonates, cyanides, carbides and oxides of carbon organic compounds are those in which carbon atoms are almost always bonded to each other, to hydrogen atoms and a few other atoms (O, N, S, P) inorganic exceptions are the oxides of carbon, carbonates, cyanides and carbides (no C-C bonds or C-H bonds) eg) CO 2 , CaCO 3 , NaCN, SiC there are millions of organic compounds and all contain covalent bonds carbon is unique for two reasons: a) it can bond with other carbon atoms to form long chains, rings, spheres, tubes, sheets etc. b) it can form combinations of single, double and triple bonds (no other element does this!!!!) recall polarity and intermolecular forces from the chemical bonding unit polar bonds are formed when there is an uneven pull on e polar compounds are formed when the polar bonds within a molecule do not cancel each other out the presence of dipole-dipole forces and hydrogen bonding will allow polar compounds to dissolve in water, since it is also polar non-polar compounds only have LD forces between molecules and will not dissolve in water

Upload: phungcong

Post on 01-May-2018

217 views

Category:

Documents


3 download

TRANSCRIPT

Page 1: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Chemistry 30Organic Chemistry Notes

A. Carbon Compounds30-C1.1k define organic compounds as compounds containing carbon, recognizing inorganic

exceptions such as carbonates, cyanides, carbides and oxides of carbon

organic compounds are those in which carbon atoms are almost always bonded to each other, to hydrogen atoms and a few other atoms (O, N, S, P)

inorganic exceptions are the oxides of carbon, carbonates, cyanides and carbides (no C-C bonds or C-H bonds)eg) CO2, CaCO3, NaCN, SiC

there are millions of organic compounds and all contain covalent bonds carbon is unique for two reasons:

a) it can bond with other carbon atoms to form long chains, rings, spheres, tubes, sheets etc.

b) it can form combinations of single, double and triple bonds (no other element does this!!!!)

recall polarity and intermolecular forces from the chemical bonding unit polar bonds are formed when there is an uneven pull on e

polar compounds are formed when the polar bonds within a molecule do not cancel each other out

the presence of dipole-dipole forces and hydrogen bonding will allow polar compounds to dissolve in water, since it is also polar

non-polar compounds only have LD forces between molecules and will not dissolve in water

30-C1.2s perform an experiment to compare the properties of organic compounds with inorganic compounds, considering properties such as solubility, viscosity, density, conductivity and reactivity

B. Structural Isomers30-C1.5k define structural isomerism as compounds having the same empirical formulas, but

with different structural formulas, and relate the structures to variations in the properties of the isomers

isomers are compounds with the same molecular formula but a different structure

Example 1Draw the three structural isomers for C5H12.

Page 2: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

1. 2. 3.

Example 2Draw three structural isomers for C4H8F2.

1. 2. 3.

30-C1.3s compile and organize data to compare the properties of structural isomers

different structures result in different properties the arrangement of the atoms determines the types of intermolecular

attractions which then determines properties such as boiling point and solubility in water

ExampleDraw two isomers of C3H8O. Which one would have a boiling point of 7.4C and which would have a boiling point of 82.5C? Explain why the boiling points are so different.

C. Formulas and Structural Diagrams organic molecules can be drawn in three different ways:

H

H

C

H

H

C C C C

H H

H

H H

H

H

H

H

H C H3 H

H

C C C C

H H

H

H

H

H

H C H3

C C C

CH3 H

H

H

H

H

H F

F

C C C C

H H

H

H H

H

H

F H

F

C C C C

H H

H

H H

H

H

H H

F

C C C C

H F

H

H H

H

H

H

C C C H

H H

H

OH H

H

H H

H

C O C C

H

H

H

H

82.5C – has HB between molecules which makes the boiling point quite high

7.4C – does not have HB between molecules therefore the boiling point is significantly lower

Page 3: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

1. complete structural diagram – shows all bondseg) C3H8

C3H7F

2. condensed structural diagrams – shows carbon to carbon bonds but includes the hydrogens etc. attached to each carboneg) C3H8

C3H7F

3. line structural diagrams – shows only carbon to carbon bonds

eg) C3H8

C5H12

C4H8

30-C1.2s build molecular models depicting the structures of selected organic and inorganic compounds

Your Assignment: pg 1

D. Prefixes 1. Number of Functional Groups

H

H

C C C H

H H

H

H H

H

H

C C C F

H H

H

H H

CH3 CH2 CH3

CH3 CH2 CH2F

Page 4: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

6 = hexa2 = di 7 = hepta3 = tri 8 = octa4 = tetra 9 = nona5 = penta 10 = deca

2. Number of Carbons1 = meth 6 = hex2 = eth 7 = hept3 = prop 8 = oct4 = but 9 = non5 = pent 10 = dec

30-C1.2k identify and describe significant organic compounds in daily life, demonstrating generalized knowledge of their origins and applications

30-C1.3k name and draw structural, condensed structural and line diagrams and formulas, using IUPAC nomenclature guidelines, for saturated and unsaturated aliphatic (including cyclic) and aromatic carbon compounds

30-C1.1sts explain how science and technology are developed to meet societal needs and expand human capability

30-C1.2sts explain that science and technology have influenced, and been influenced by, historical development and societal needs

30-C1.3s follow appropriated IUPAC guidelines when writing the names and formulas of organic compounds

E. Alkanes CnH2n+2

eg) C5H12, C20H42, etc. hydrocarbons containing only single bonds ie) they are SATURATED can be long continuous chains, branched chains, ring structures

(cycloalkanes)

1. Properties nonpolar not soluble in water can be solid, liquid or gas depending on number of carbon atoms relatively unreactive because the single bonds are very stable

2. Uses natural gas, BBQ’s, lighter fluid, gasoline etc good for making plastics, lubricants

Page 5: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

3. Naming IUPAC = International Union of Pure and Applied Chemistry

i. Continuous Chains prefix + “ANE” (suffix)

eg)

ii. Branched Chains branches are called alkyl functional group 1 C = methyl; 2C = ethyl; 3 C = propyl etc find the longest carbon chain and number it so the branches get the

lowest possible numbers to name: name the groups first (in alphabetical order), including the

number of the carbon where each group is found, then name the longest chain (parent name)

eg)

H

H

H

H

H

C C C C

H H

H

H H

butane

H

CH2

C

H

H

C C C C

H H

H

CH3 H

H

H

H

CH3

methylethyl

541 323-ethyl-2-methylpentane

H

CH3

C

H

H

C C C C

H H

H

H H

H

H

H

methyl

541 323-methylpentane

H

C

H

C C C C

H H

H

H

H 541 32

2,3-dimethylpentane

Page 6: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Try These:1.

2.

3.

4.

Try TheseDraw the structure for each of the following compounds:

1. 2,2-dimethylpropane

2. 4-ethyl-2,3-dimethylhexane

CH3 H CH3 H H

methylmethyl

H

H

C

CH3

H

C C C C

H H

H

CH3 H

H

C

H H

H

H 2,4-dimethylhexane

H

H

C

CH3

H

C C C C

H H

H

CH2 H

H

CH3

H

H 2,4-dimethylhexane

CH3 CH CH2 CH

CH3

CH2

CH3 CH3 CH

CH3

2,4,6-trimethylheptane

CH3 C CH2 C

CH3

CH3

CH3 CH3

CH3

2,2,4,4-tetramethylpentane

CH3 C CH3

CH3

CH3

CH3 CH CH2 CH

C2H5

CH2

CH3

CH3

CH3

Page 7: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

3. 4-propyloctane

4. 3,5-diethyl-4-methylheptane

Your Assignment: pgs 2-3 in workbook

iii. Cycloalkanes use the ring structure as the “parent” name “cyclo” + prefix + “ANE”

eg)

if there are branches, number the carbons in the ring so the branches get the lowest possible number sequence

CH3 CH CH2 CH

C2H5

CH2

CH3

CH3

CH3

CH3 CH2 CH2 CH

C3H7

CH2 CH2 CH2 CH3

cyclobutane

cyclopropane

Page 8: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

eg)

Try These:

1.

2.

3.

4. 1,2-dimethylcyclopropane

5. 1,1,2,2-tetraethylcyclohexane

CH3

CH3 CH21

2

4

5

3

1-ethyl-3-methylcyclopentane

CH3

CH3

1,2-dimethylcyclobutane

CH2 CH3

CH2 CH3

1,1-diethylcyclohexane

CH2 CH2

CH2 CH3

CH2 CH2

CH3

CH3

4,6-diethyl-2-methyl-1-propylcyclooctane

CH3 CH3

CH2 CH3

CH2 CH3

Page 9: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

6. 3-butyl-1,1,2-trimethylcyclopentane

Your Assignment: pg 4 in workbook

C. Alkenes CnH2n

eg) C5H10, C20H40, etc. hydrocarbons containing one or more double bonds ie) they are

UNSATURATED can be long continuous chains, branched chains, ring structures

(cycloalkenes)

1. Properties30-C1.3s interpret the results of a test to distinguish between a saturated and an unsaturated

aliphatic, using aqueous bromine or potassium permanganate solutions

nonpolar not soluble in water lower boiling point than corresponding alkane because they have fewer

e which makes the LD forces of attraction weakereg) ethane BP = 88.6C ethene BP = 103.8C

more reactive than alkanes double bond has more e- in the same area greater repulsion and

bond less stable diagnostic test: use KmnO4(aq) or Br2(l) ***alkenes (double bond) will

react with these substances causing a noticeable colour change, alkanes will not

CH2 CH3

CH2 CH3

CH2 CH2 CH3

CH3

CH3

CH3

A B A BBr2(l) KMnO4(l)

alkene alkenealkane alkane

Page 10: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

***the alkenes will react causing the colour to disappear as the coloured substance is used up in the reaction

2. Uses plastics (PVC) steroids welding torches

3. Namingi. Continuous Chains prefix + “ENE” (suffix) number carbons to give the double bond the lowest number the number where the double bond starts is to be given as a “ # ”

between the prefix and the suffix

eg) H

C

H

C C C C

H H

H

H H

H

C

H H

H

H hex-3-ene‗

H

C

H

C C C

H

H

H

H

C

H H

H

H pent-2-ene‗

H

C

H

C C

H

H

C

H H

H

H but-1-ene‗

Page 11: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

ii. Branched Chains find the longest carbon chain and number it so the double bond gets the

lowest number to name: name the groups first (in alphabetical order), including the

number of the carbon where each is found, then the parent name including the number of the carbon where the double bond starts

eg)

Your Assignment: pgs 5-6 in workbook

iii. Cycloalkenes double bond is always numbered 1,2 branches get the lowest numbering sequence after the double bond “cyclo” + prefix + “ENE” list branches in alphabetical order with the number of the carbon they

are on

eg)

2-ethylhept-1-ene CH2 CH2 C CH2

CH2

CH2 ‗

CH2 CH3

CH3

CH CH3 CH CH

CH2

CH ‗

CH CH3

CH2

CH3

CH3 CH3

4,5,6-trimethylnon-2-ene

cyclohexene

cyclopropene

Page 12: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Your Assignment: pg 7 in workbook

D. Alkynes CnH2n-2

eg) C5H8, C20H38, etc. hydrocarbons containing one or more triple bonds ie) they are also

UNSATURATED can be long continuous chains, branched chains not plentiful in nature

1. Properties nonpolar very reactive (more than alkanes and alkenes) triple bond has 6 e- in the same area high force of repulsion boiling points are higher than corresponding alkanes and alkenes

because of their linear structure and the nature of triple bonds

2. Uses welding torches

3. Namingi. Continuous Chains

CH2 CH3

3-ethylcyclobutene

CH2 CH3

CH3

CH3

3-ethyl-1,3-dimethylcyclobutene

Page 13: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

prefix + “YNE” number carbons to give the triple bond the lowest number the number where the triple bond starts is to be given as a “ # ”

between the prefix and the suffixeg)

ii. Branched Chains find the longest carbon chain and number it so the triple bond gets the

lowest number to name: name the groups first (in alphabetical order), including the

number of the carbon where each is found, then the parent name including the number of the carbon where the triple bond starts

eg)

Your Assignment: pg 8 in workbookReview

alkanes – branches, rings – least reactive alkenes – branches, rings alkynes – branches – most reactive all called aliphatics

C C C C C

H H

H

H H

H

C

H H

H

H hex-3-yne≡

C C C C

H

H

H

H

C

H H

H

H pent-2-yne

C CH3 CH C

CH2

CH ≡ CH CH3

CH3

CH3 CH3

2,5,6-trimethyloct-3-yne

3-propyloct-1-yne CH2 CH C CH

CH2

CH2 ≡ CH2 CH3

CH2 CH2

CH2

Page 14: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

all nonpolar and not soluble in water major intermolecular forces are LD boiling points are low

E. Aromatics hydrocarbons containing one or more benzene rings

all bonds are the same length and strength we draw benzene like this:

1. Properties nonpolar the benzene ring structure is very stable aromatics are characterized by strong aromas

2. Uses ASA, amphetamines, adrenaline, benzocaine (anesthetic) moth balls, TNT wintergreen, menthol, vanilla, cinnamon SPF in sunscreen

3. Namingi. Benzene as a Branch if you have a really long carbon chain, it is easier to call the benzene

ring a “phenyl” group

eg)

OR

CH3 CH2 CH2 CH CH2 CH3 CH2 4-phenyloctane

CH2 CH2 CH CH C ‗

CH2 CH2

CH3

CH3 3-methyl-5,5-diphenyloct-1-ene

Page 15: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

ii. Benzene as the Main Compound if only one group is attached, give the alkyl name attached to

“benzene” (no number is necessary)

eg)

if there is more than one branch, number them so they get the lowest sequence and name alphabetically (just like before)

eg)

***watch out for this!

CH3 methylbenzene

CH3

CH3

CH3

CH3

C2H5

CH3

CH3

CH2 CH2

CH2

1-ethyl-3-methylbenzene

1,3-dimethyl-5-propylbenzene

1-ethyl-3-methylcyclohexane

Page 16: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Your Assignment: pgs 9-10 in workbook

30-C1.4k identify types of compounds from the hydroxyl, carboxyl, ester linkage and halogen functional groups, given the structural formula

F. Alcohols R - OH

organic compounds with one or more OH (hydroxyl) groups

1. Properties have much higher boiling points than corresponding aliphatics

because of hydrogen bonding!eg) methane (CH4) BP = 162C

methanol (CH3OH) BP = 65C polar the –OH end of the alcohol is polar while the carbon chain end is

not small alcohols are soluble in water and large alcohols are not

2. Uses antifreeze, rubbing alcohol, beverages, moistening agent

3. Naming number the longest carbon chain containing the hydroxyl group so

the –OH group gets the lowest number aliphatic name (without “e” at end) + “OL” give the number for the carbon where the –OH group is found

between the parent name and the suffix if there is more than one hydroxyl group, use a prefix (di, tri,

tetra) to indicate the number of OH groups and place the numbers between the parent name and the suffix***Note, if the suffix starts with a vowel, drop the “e” on the parent name; if the suffix starts with a consonant, keep the “e” on the parent name

eg) H

OH

H

H

H

C C C C

H H

H

H H

butan-2-ol

Page 17: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

an unusual case:

Your Assignment: pg 11 in workbook

H

OH

H

H

H

C C C C

CH3 H

H

H H

3-methylbutan-2-ol

OH

phenol

H

OH

H

H

H

C C C C

CH3 H

H

OH H

2-methylbutane-2,3-diol

Page 18: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

G. Organic Halides R - X where R is carbon chain and X is a halogen organic compounds where hydrogen has been replaced by one or

more halogens (F, Cl, Br, I) do not readily occur in nature

1. Properties can be polar or nonpolar, depending on the placement of the halogen

groups many are toxic and dangerous

2. Uses manufactured for human use eg) DDT, PCB, CFC anesthetics dry cleaning fluid plastics, polymers (Teflon)

3. Naming same rules as before…name branches (halogens included now)

alphabetically F = fluoro Cl = chloro Br = bromo I = iodo

eg)

Your Assignment: pg 12 in workbook

Cl

H

H

H

H

C C C C

Cl H

H

H H

2,3-dichlorobutane

F

CH3

I

2-fluoro-4-iodo-1-methylbenzene

Page 19: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

H. Carboxylic Acids

where R is carbon chain organic compounds containing the carboxyl functional group

(COOH)

1. Properties polar dissolve in water high boiling points due to hydrogen bonding weakly acidic diagnostic test: use litmus paper (will turn red), readily react with

metals, neutralize bases

2. Uses recycling rubber – methanoic acid vinegar – ethanoic (acetic) acid rust remover – oxalic acid fruits – citric acid

3. Naming count the longest carbon chain including the carbon in the carboxyl

group the carbon in the carboxyl group is always number 1 drop “e” and add “OIC ACID”

eg)

OH

O

CH

methanoic acid

ethanoic acidOH

O

CC

H

H

H

OH

O

Cbenzoic acid

OH║O

R C

Page 20: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Your Assignment: pg 13 in workbook

I. Esters

where R can be a carbon chain or hydrogen and R’ can be a carbon chain

combination of a carboxylic acid and an alcohol

1. Properties polar small esters dissolve in water, large esters do not boiling points slightly lower than corresponding carboxylic acids and

alcohols due to lack of hydrogen bonding very volatile which allows them to generate aromas

2. Uses flavouring agents

3. Naming identify the alcohol used to make the ester change the alcohol name to the corresponding alkyl name

eg) methanol would become methyl identify the carboxylic acid the ester was made from drop the “oic acid” and replace with “oate”

eg) butanoic acid would become “butanoate” put the two names together with a space in between

eg) methyl butanoate you can have branches on esters…they follow the alphabetical rule,

numbering begins at the O end of the alcohol and the C=O end of the carboxylic acid

OH

O

CC

H

H

CC

H

H H

H

I4-iodobutanoic acid

O R’║O

R C

Page 21: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

eg)

Your Assignment: pg 14 in workbook

J. Boiling Points and Solubility30-C1.6k compare, both within a homologous series and among compounds with different

functional groups, the boiling points and solubility of examples of aliphatics, aromatics, alcohols and carboxylic acids

we can compare the boiling points of various organic compounds using their polarity and the intermolecular attractions between the molecules

Example 1Put the following organic compounds in order from highest boiling point to lowest boiling point.

alcohol, alkane, alkene, aromatic, carboxylic acid

alcohol, carboxylic acid, aromatic, alkane, alkene

O

O

CC

H

H

CC

H

H H

H

H C

H

C

H

H

H

H ethyl butanoate

O

O

CC

H

H

C

H

H

H C

H

C

CH3

H

H

Hpropyl propanoate

O

O

CC

H

CH3

C

H

CH3

H C

H

C

H

H

H

H ethyl 2-methylbutanoate

highest lowest

Page 22: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Example 2Put the following homologous series of organic compounds in order from highest boiling point to lowest boiling point.

C2H6, C2H5OH, CH3COOH, C2H4

C2H5OH, CH3COOH, C2H6, C2H4

we can also compare the solubility of various organic compounds using their polarity

Insoluble Organic Compounds Soluble Organic Compoundsaliphatics – alkanes, alkenes, alkynes

carboxylic acids

aromaticsalcohols – large (7 or more carbons)

alcohols – small (less than 7 carbons)

esters – large esters – small organic halides organic halides

K. Organic Reactions30-C2.1k define, illustrate and provide examples of simple addition, substitution, elimination,

esterification and combustion reactions30-C2.2k predict products and write and interpret balanced equations for the above reactions30-C2.4k relate the reactions described above to major reactions that produce thermal energy

and economically important compounds from fossil fuels30-C2.3s use IUPAC conventions when writing organic chemical reactions

1. Combustion Reactions occurs when a hydrocarbon reacts with oxygen products are always carbon dioxide and water (vapour or liquid) these are economically important reactions for they are the major

reactions that produce thermal energy required for fuelling our vehicles, heating our homes, and producing electricity

eg) 1 C5H12(l) + 8 O2(g) 5 CO2(g) + 6 H2O(g)

+ 6.5 O2(g) 4 CO2(g) + 5 H2O(g) H

H

H

H

H

C C C C

H H

H

H H

highest lowest

Page 23: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

2. Addition Reactions a double or triple bond in an alkene or alkyne is broken and a group

or element is added

eg)

Try These:1.

H H

C C

H H

‗ Cl Cl +

H

Cl

H C C H

H

Cl

H H

C C

H H

‗ H OH +

H

OH

H C C H

H

H

H H

C C

H H

‗ H H +

H

H

H C C H

H

H

H H

C C

H H

‗ + H Br

H

Br

H C C H

H

H

C C H H ≡ 1 Cl2 +

C C H H ≡ 2 Cl2 + Cl

Cl

H C C H

Cl

Cl

H H

C C

Cl Cl

H

C

H

C C

H

H

C

H H

H

H ‗

Br2 + Br

H

H C C C

Br

H

H

H

C

H

H

H

Page 24: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

2.

3.

Your Assignment: pg 15

H

C

H

C C C

H

H

H

H

C

H H

H

H ‗

HCl + H

H

H C C C

H

H

Cl

H

C

H

H

C

H

H

H

C C C C

H

H

H

H

H

H ≡ 1 Cl2 + Cl

C

Cl

C C C

H

H

H

H

H

H

Page 25: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

3. Substitution Reactions the replacement (substitution) of a hydrogen on an alkane or aromatic

with another atom (eg. F, Cl etc) commonly used to make organic halides

Examples:

C H

H

H

H Cl – Cl

+ cat

C H

H

Cl

H H - Cl +

Br – Br

+ cat H - Br +

Br

I – I + cat H - I +

I

1.

2.

3.

4.

H

H

H C C C

H

H

H

H

C

H

H

H

Br

H

H C C C

H

H

H

H

C

H

H

H Br2 + cat H - Br +

Page 26: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

4. Esterification Reactions30-C2.1s predict the ester formed from an alcohol and an organic acid

the reaction of a carboxylic acid with an alcohol to form an ester the catalyst is sulphuric acid

Examples:

5. Elimination Reactions an alcohol has water removed, forming and alkene plus the water organic halides can react with a base (hydroxide) to produce an

alkene, a halide ion and water

Examples:

1.

2.

OH

O

CH H

H

H

HO C + H2SO4(aq)O

O

CH H

H

H

C + H – OH

H2SO4(aq)+ H – OH OH

O

CCH C

H

H

H

H

+ C

H

H

HO C

H

H

H C

H

H

C

H

H

H O

O

CCH C

H

H

H

H

H

H

OH

H

H

H C C cat H H

C C

H H

‗ + H – OH

1.

2. H

H

H

H

H

C C C C

H H

H

H OH

cat H

C

H

C C

H

H

C

H H

H

H ‗ H – OH +

Page 27: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

3.

Your Assignment: pgs 16 - 17

6. Polymerization Reactions30-C1.2sts explain that science and technology have influenced, and been influenced by,

historical development and societal needs30-C2.3k define, illustrate and provide examples of monomers, polymers and polymerization

in living systems and nonliving systems30-C2.3s draw or use models to illustrate polymers

a monomer is a simple molecule that forms the base unit for a polymer

a polymer is a very, very long molecule formed by the covalent bonding of bazillions of monomers

depending on the polymer, the monomers that make it up can be the same or different

polymers can be natural eg) carbohydrates, proteins, DNA

polymers can be synthetic eg) nylon, PVC, Teflon, polyester

polymers that can be heated and molded into specific shapes are commonly called plastics

plastics are one type of synthetic compound that has been of great benefit to society (although there are also problems associated with then)

the names of polymers are the monomer name with “poly” in front many have classical names instead of IUPAC names

Addition Polymers formed when the electrons in double or triple bonds in the monomer

units are rearranged the polymer is the only product formed

H

H

Cl

H

H

H C C + OH cat H H

C C

H H

‗ + H – OH + Cl

Page 28: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Examples:

2.

F F

C C

F F

‗ +

F F

C C

F F

‗ cat

F

F F

F

C C C C

F F

F F n

Teflon

∙∙∙ ∙∙∙

1. H H

C C

H H

‗ +

H H

C C

H H

‗ cat

H

H H

H

C C C C

H H

H H n

polyethene

∙∙∙∙∙∙

H Cl

C C

H H

‗ +

H Cl

C C

H H

‗ cat

H

H H

Cl

C C C C

Cl H

H H n

3.

polyvinylchloride (PVC)

∙∙∙ ∙∙∙

4.

H H

C C

H

‗ +

H H

C C

H

‗ cat

H

H

H

C C C C

H H

H n

polystyrene (Styrofoam)

∙∙∙∙∙∙

Page 29: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

Condensation Polymers polymerization reactions that involve the formation of a small

molecule (commonly water) as well as the polymer each monomer must have two functional groups two common linkages formed:

1. ester linkage – between carboxyl group (COOH) and hydroxyl group (OH)

2. amide linkage – between amino group (NH2) and carboxyl group (COOH)

Examples:

1.

polyethylene terephthalate PET

n

∙∙∙∙∙∙ C C O

O ║

O

O ║

C C

H H

H H

+ H2O

C C cat

C C OH

O O

HO

║ OH HO

H H

H H

+ ║

ester linkage

cat

2.

C C H

O H

HO N ║

H

H

C C H

O H

HO N ║

H

H

+

n

∙∙∙∙∙∙ + H2O C C

O H

N ║

H

H

C C

O H

N ║

H

H

protein

amide linkage

Page 30: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

L. Petroleum Refining30-C1.7k describe, in general terms, the physical, chemical and technological processes used

to separate organic compounds from natural mixtures or solutions30-C2.1sts explain how science and technology are developed to meet societal needs and

expand human capability

Alberta has vast reserves of petroleum in the form of natural gas, crude oil and oil sand deposits

most of this petroleum is refined and then burned as fuel petrochemicals, basic hydrocarbon raw materials such as ethane and

propene, are also used in the production of plastics refining of petroleum separates the crude mixture into purified

components fractional distillation is used to separate the components distillation works because of the different boiling points of the

components of petroleum the lighter the molecule and the lower the boiling point, the higher it

rises in the tower (asphalt, fuel oil, wax at bottom; gasoline at top) there are two types of reactions in petroleum refining:

1. Cracking breaks long chain hydrocarbons into smaller units cracking requires heat and pressure there are many different types of cracking reactions, forming different

products (alkanes, alkenes)eg) catalytic cracking, steam cracking, hydrocracking

hydrocracking requires H2(g)

Examples:1. C17H36 + H2 C9H20 + C8H18 cat

2.

CH3 CH2 CH2 CH3 + cat

+ CH3 CH2 CH3 H2CH3 CH2 CH2 CH2 CH3 CH2 CH2

Page 31: Chemistry 20 - SharpSchoolcompositehighfmpsd.sharpschool.com/UserFiles/Servers... · Web viewthe same molecular formula but a different structure Example 1 Draw the three structural

2. Reforming small hydrocarbons are joined to make larger molecules requires heat and pressure there are several types of reforming reactions

eg) alkylation to produce “high octane” gasoline all reforming reactions produce H2(g)

Examples:

1. C7H16 + C12H26 C19H40 + H2

2. ethane + octane decane + hydrogen gas

30-C1.1s design a procedure to separate a mixture of organic compounds, based on boiling point differences

Your Assignment: pgs 18-19Separate an Organic Mixture – pg 581

cat

cat