organic notes 2011

5/12/2018 Organic Notes 2011 - slidepdf.com

http://slidepdf.com/reader/full/organic-notes-2011 1/99

A. Carbon Compounds

organic compounds are those in which atomsare almost always bonded to each other, toatoms and a few other atoms

Organic Chemistry

inorganic exceptions are the oxides of carbon,

and carbidescyanidescarbonates,

eg) CO2, CaCO3, NaCN, SiC

(O, N, S, P)

(no C-C bonds or C-H bonds)

carbonhydrogen



Sample Diploma QuestionUse the following information to answer the next

question.

Chemical Compounds1 CO(g) 5 C2H5OH(l)

2 Na2CO3(aq) 6 KCN(g)3 CH4(g) 7 CoCl2(aq)4 HOOCCOOH(aq) 8 CH3COOH(aq)

The chemical compounds numbered above thatrepresent organic compounds are _______,

_______, _______, and _______.



carbon is unique for two reasons:it can bond with atoms toform long chains, rings, spheres, tubes,sheets etc.

a)

b) it can form combinations of

single, double and triple bonds

(no other element does this!!!!)

other carbon

there are of organic compounds andall contain covalent bonds

millions



recall polarity and intermolecular forces from thechemical bonding unit

polar bonds are formed when there is anpull on e

compounds are formed when the polar bonds within a molecule each otherout

the presence of forces and will allow polar compounds to

, since it is also polar

compounds only have LD forces between molecules and dissolve in water

uneven

polardo not cancel

dipole-dipole

hydrogen bonding

dissolve in waternon-polar

will not



B. Structural Isomers

isomers are compounds with the same molecularformula but a different structure



Example 1

Draw the three structural isomers for C5H12.

H

H

C

H

H

C C C C

HH

H

HH

H

H

H

H

HCH3 H

H

C C C C

HH

H

H

H

H

HC H3

C C C

CH3H

H

H

H

1. 2.

3.



Example 2

Draw three structural isomers for C4H8F2 .

H

FH H

F

C C C C

HH

H

H

H

1. 2.

3. H

HF H

F

C C C C

HH

H

H

H

H

HH F

F

C C C C

HH

H

H

H



different structures result in different properties

the arrangement of the atoms determines the types of intermolecular attractions which then determinesproperties such as andin water

boiling point solubility



Example

Draw two isomers of C3H8O.

Which one would have a boiling point of 7.4 C and which would have a boilingpoint of 82.5rC? Explain why the boiling points are sodifferent.

H

H

C C C H

HH

H

OHH

H

H H

H

C O C C

H

H

H

H

has HB

between molecules

which makes the boiling

point quite high

does not have HB

between molecules

therefore the boiling point

is significantly lower

82.5rC ± 7.4rC ±



C. Formulas and Structural Diagrams

organic molecules can be drawn in three different ways:

1. complete structural diagram ± shows all bonds

eg) C3H8 H

H

C C C H

HH

H

HH

eg) C3H7F H

H

C C C F

HH

H

HH



2. condensed structural diagrams ± shows

but includes the e.

attached to each carbon

eg) C3H8

eg) C3H7F

CH3 CH2 CH3

CH3 CH2 CH2F

hydrogens

carbon to

carbon bonds



3. line structural diagrams ± shows only bonds

carbon tocarbon

eg) C3H8

eg) C5H12

eg) C4H8



Sample Diploma Question

The structural diagram below that is an isomer of pentane, C5H12, is

H

C

H

C C

H

H

C

H H

H

H

C

C

H

C

C

H

C

HH

H

H

H

H

C H

CH

C

H

C

C

H

C

HH

H

H

H

H

CH

H

H

H

C

H

C

H

C

H

H

H

H

CH

H

H

H

D.

B. A.

C.



D. Prefixes1. Number of Functional Groups

6 = hexa

2 = di 7 = hepta

3 = tri 8 = octa

4 = tetra 9 = nona

5 = penta 10 = deca



2. Number of Carbons

1 = 6 =

2 = 7 =

3 = 8 =

4 = 9 =

5 = 10 =

meth

eth

prop

but

pent

hex

hept

oct

non

dec



E. Alkanes

hydrocarbons containing

CnH2n+2

eg) C5H12, C20H42, etc.

can be continuous chains, chains,structures

only single bonds

SATURATED

ring

ie) they are

long branched

(cycloalkanes)



1. Properties

can be depending onnumber of carbon atoms

relatively because the bondsare

nonpolar@not soluble

solid, liquid or gas

very stableunreactive single

in water



2. Uses

natural gas, BBQ¶s, lighter fluid, gasoline etc

good for making plastics, lubricants

3. Naming

IUPA C = International Union of Pure and A ppliedChemistry



i. Continuous Chains

prefix + ³ANE´ (suffix)

eg) H

H

H

H

H

C C C C

HH

H

HH

butane



ii. Branched Chains

branches are called functional group

1 C = ; 2C = ; 3 C = etc

alk yl

meth yl eth yl prop yl

find the andso the branches get the

longest carbon chain number it

lowest

to name: name the first (inorder), including the where

each group is found, then name the

groups alphabetical

number of the carbon

longest chain

possible numbers

(parent name)



eg)3-methylpentane

H

CH3

C

H

H

C C C C

HH

H

HH

H

H

H

1 2 3 4 5

methyl

H

CH2

C

H

H

C C C C

HH

H

CH3H

H

H

H

CH3

1 2 3 4 5

methyl

ethyl

3-ethyl-2-methylpentane



eg)

2,3-dimethylpentane

H

CH3

C

CH3

H

C C C C

HH

H

HH

H

H

H

54321

methylmethyl



Sample Diploma Question Which of the following line diagrams represents

2,3-dimethylpentane?

D.

B. A.

C.



iii. Cycloalkanes

use the as the name

+ +

eg)

ring structure ³parent´

prefix³cyclo´ ANE

cyclobutane

cyclopropane



if there are branches, number the carbons in the ring

so the branches get the lowest number sequence

CH3

CH3CH2

eg)

1

23

4 5

ethyl

methyl

1-ethyl-3-methylcyclopentane



F. Alkenes


CnH2n

eg) C5H10, C20H40, etc.

one or more double

bondsie) they are

can be continuous chains, chains,

structures

branchedlong

ring (cycloalkenes)

UNSATURATED



1. Properties

double bond has in the same area@ and

nonpolar@not soluble

than corresponding alkane because they have which makes theforces of attraction

eg) ethane BP =

88.6rC ethene BP =

103.8

rC

lower boiling pointfewer e LD

weaker

more e-

greater repulsion bond less stable

than alkanesmore reactive

in water



A B A BBr2(l) KMnO4(l)

alkene alkenealkane alkane

*** the alkenes will react causing the colour todisappear as the coloured substance is used up in

the reaction

diagnostic test: use KMnO4(aq) or Br2(l)

***alkenes with these

substances causing a noticeablealkanes will not

(double bond) will react

colour change,



2. Uses

plastics (PV C)

steroids

3. Naming

welding torches


prefix + double bond # + ³ENE´ (suffix)

number carbons to give the thedouble bond

lowest number the number where the double bond is to be

given as a ³ # ´ between the prefix and the suffixstarts



eg)

H

C

H

C C C C

HH

H

HH

H

C

H H

H

H

H

C

H

C C C

H

H

H

H

C

H H

H

H

H

C

H

C C

H

H

C

H H

H

H

hex-3-ene

pent-2-ene

but-1-ene



ii. Branched Chains

find the longest carbon chain and number it so thegets the lowest possible number

to name: name the first (inorder), including the of the carbon

where each is found, then theincluding the of the carbon wherethe double bond starts

double bond

groups alphabeticalnumber

parent name

number



CH2CH2 C CH2

CH2

CH2 CH2 CH3

CH3

eg)

CHCH3 CH CH

CH2

CH

CH CH3

CH2

CH3

CH3CH3

2-ethylhept-1-ene

4,5,6-trimethylnon-2-ene



iii. Cycloalkenes

double bond is always numbered

+ +prefix³cyclo´ ENE

1, 2

get theafter the branches lowest numbering sequence

double bond

list branches in with the

number

alphabetical order

of the carbon they are on



CH2 CH3

CH2 CH3

CH3

CH3

3-ethylcyclobutene

3-ethyl-1,3-dimethylcyclobutene

1

1

2

2

3

3

4

4

eg) cyclohexene

cyclopropene



G. Alkynes


CnH2n-2

eg) C5H8, C20H38, etc.

can be continuous chains, chains

one or more triple bonds

ie) they are also

not plentiful in nature

UNSATURATED

long branched



1. Properties

bond has in the same area @ forceof repulsion

very reactive

boiling points are than correspondingalkanes and alkenes because of theirand the of triple bonds

2. Uses

welding torches

nonpolar

(more than alkanes and alkenes)

higherlinear structure

nature

triple 6 e- high




prefix + triple bond # + ³ Y NE´

number carbons to give the thetriple bondlowest number

3. Naming

the number where the triple bond is to be given as a ³ # ´ between the prefix and thesuffix

starts



eg)

hex-3-yneCC C C C

HH

H

HH

H

C

H H

H

H

CC C C

H

H

H

H

C

H H

H

H pent-2-yne



ii. Branched Chains

find the and number it so thegets the lowest number

to name:name the first (in order),including the of the carbon where each isfound, then the including the

of the carbon where the triple bond starts

triple bond

longest carbon chain

groups alphabeticalnumber

parent name

number



eg)CH

2CH C CH

CH2

CH2

CH2 CH3

CH2 CH3

CH2

3-propyloct-1-yne

CCH3 CH C

CH2

CH CH CH3

CH3

CH3CH3

2,5,6-trimethyloct-3-yne



Review

alkanes ± branches, rings ± least reactive

alkenes ± branches, rings

alkynes ± branches ± most reactive

all called

major intermolecular forces are@ boiling points are

aliphatics

LDlow

all and in waternonpolar not soluble



H. Aromatics

hydrocarbons containing one or more

all bonds are the

benzene rings C6H6

OR

same length and strength

@ we draw benzene like this:



1. Properties

the benzene ring structure is

aromatics are characterized by strong aromas

very stable

nonpolar



2. Uses

A S A , amphetamines, adrenaline, benzocaine(anesthetic)

moth balls, TNT

wintergreen, menthol, vanilla, cinnamon

SPF in sunscreen



3. Naming

i. Benzene as a Branch

if you have a really long carbon chain, it is easierto call the benzene ring a ³phenyl´ group

eg)

CH3 CH2CH2 CH CH2 CH3CH2

CH2CH2 CH CH C

CH2 CH2

CH3

CH3

4-phenylheptane

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



ii. Benzene as a the Main Compound

if only one group is attached, give theattached to alkyl name³benzene´

(no number is necessary)

eg)

CH3 methylbenzene



if there is more than one branch, number them sothey get the and name

eg)1-ethyl-3-methylbenzene

1,3-dimethyl-5-propylbenzene

lowest sequence

alphabetically

CH3

CH3CH2

CH3

CH3

CH3

CH2CH2



I. Alcohols

organic compounds with one or more

R -OH

OH (hydroxyl) groups

1. Properties

have much thancorresponding aliphatics because of

eg) methane (CH4) BP =methanol (CH3OH) BP =

-162rC

65rC

higher boiling pointshydrogen

bonding!



2. Uses

antifreeze, rubbing alcohol, beverages, moisteningagent

the end of the alcohol is while theend @ small alcohols are

in water and large alcohols are

±OH polarcarbon chain is not

soluble not

polar



3. Naming

number the longest carbon chain containing the

so the group gets thehydroxyl group

name at end

give the where theis found between the parent name and

the suffix

number for the carbon±OH group

±OH

lowest number

+ ³OL´aliphatic (without ³e´ )



if there is hydroxyl group, use a

prefix ( ) to indicate theof OH groups and place the numbers between theparent name and the suffix

***Note, if the suffix starts with a vowel, drop the ³e´on the parent name; if the suffix starts with aconsonant, keep the ³e´ on the parent name

more than onedi, tri, tetra number



H

OH

H

H

H

C C C C

HH

H

HH

eg)

H

OH

H

H

H

C C C C

CH3H

H

HH

butan-2-ol

3-methylbutan-2-ol



H

OH

H

H

H

C C C C

CH3H

H

OHH

simplest aromatic alcohol: OH

2-methylbutane-2,3-diol

phenol



J. Organic Halides

where is and

R - X

R carbon chain or ring Xhalogen

organic compounds where has been

replaced by one or more halogens (F, Cl, Br, I)

do not readily occur in nature

hydrogen



1. Properties

can be or , depending onthe placement of the halogen groups

many are

2. Uses

toxic and dangerous

anesthetics

dry cleaning fluid

plastics, polymers (Teflon)

manufactured for human use eg) DDT, PCB, CFC

polar nonpolar



3. Naming

same rules as before« name branches (included now)

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

eg) Cl

H

H

H

H

C C C C

ClH

H

HH

2,3-dichlorobutane

halogensalphabetically



F CH3

I

2-fluoro-4-iodo-1-methylbenzene



K. Carboxylic Acids

where isR carbon chain or ring

organic compounds containing the

OHO

R C

carboxylfunctional group (-COOH)

1. Properties

polar@ dissolve in water

boiling points due to

weakly acidic

diagnostic test: use (will turn ),

metals, neutralize bases

high hydrogen bonding

litmus paper red

readily react with

considered since double bonds in

functional groups are not taken into account

saturated



2. Uses

vinegar ± ethanoic (acetic) acid

rust remover ± oxalic acid

fruits ± citric acid

recycling rubber ± methanoic acid

3. Naming

count the longest carbon chain including the

drop and add

carbon in the carboxyl group

the carbon in the carboxyl group is always number 1

³e´ ³OIC ACID´



OH

O

CH

OH

O

CC

H

H

H

eg)

methanoic acid

ethanoic acid



benzoic acid

4-iodobutanoic acid

OH

O

C

OH

O

CC

H

H

CC

H

H H

H

I

O



L. Esters

where can be a carbon chain or hydrogen andcan be a carbon chain

combination of a and an

1. Properties

esters in water, esters

boiling points slightly lower than correspondingcarboxylic acids and alcohols due to lack of hydrogen

bonding

OO

R C R¶

R R¶

carboxylic acid alcohol

small dissolve largedo not

polar

considered since double bonds infunctional groups are not taken into accountsaturated



2. Uses

flavouring agents

3. Naming identify the used to make the ester

identify the the ester wasmade from

change the alcohol name to the correspondingname

eg) methanol would become

alcohol

alkyl

methyl

carboxylic acid

very which allows them to generate volatilearomas



put the together with a in between

eg)

you can have on esters«they follow the alphabetical rule, numbering begins at the

of the alcohol and the C=O end of thecarboxylic acid

two names space

methyl butanoate

branches

O end

drop the ³oic acid´ and replace with

eg) butanoic acid would become

³oate´

³butanoate´



eg)

O

O

CC

H

H

CC

H

H H

H

H C

H

C

H

H

H

H

O

O

CC

H

H

C

H

H

H C

H

C

CH3

H

H

H

ethyl butanoate

propyl propanoate



eg)

O

O

CC

H

CH3

C

H

CH3

H C

H

C

H

H

H

H

ethyl 2-methylbutanoate




The structural diagrams that represent the aromatic, the

carboxylic acid, the unsaturated aliphatic and the halogenated

hydrocarbon, respectively, are ________, ________,

________, and ________.



M. Boiling Points and Solubility

we can compare the boiling points of various organiccompounds using their and the between the

molecules

Example 1

Put the following organic compounds in order fromhighest boiling point to lowest boiling point.

alcohol, alkane, alkene, aromatic, carboxylic acid

alkenecarboxylic acid alcohol aromatic alkane

highest lowest

polarity intermolecular attractions



Example 2

Put the following homologous series of organic

compounds in order from highest boiling point tolowest boiling point.

C2H6, C2H5OH, CH3COOH, C2H4

highest lowest

CH3COOH C2H4C2H6C2H5OH



we can also compare the of variousorganic compounds using their polarity

solubility

Insoluble Organic

Compounds

Soluble Organic

Compounds

organic halides

aliphatics ± alkanes,

alkenes, alkynes

aromatics

alcohols ± large (7 or

more carbons)

esters ± large

carboxylic acids

alcohols ± small (less

than 7 carbons)

esters ± small

organic halides



N. Organic Reactions

occurs when a reacts with

1. Combustion Reactions

hydrocarbon oxygen

products are always carbon dioxide and water

these are economically important reactions for they are

the major reactions that producerequired for fuelling our vehicles, heating our homes,and producing electricity

thermal energy

eg) C5H12(l) + O2(g) p +CO2(g) H2O(g)5 681



eg) 1 C5

H12(l)

+ 8 O2(g)

p 5 CO2(g)

+ 6 H2

O(g)

H

H

H

H

H

C C C C

HH

H

HH

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

***balance these reactions



a or bond in an alkene or alkyne

is and a group or element is

2. Addition Reactions

eg)

H H

C C

H H

Cl Cl+

p

H

Cl

H C C H

H

Cl

double triple

broken added



H

OH

H C C H

H

H

H

H

H C C H

H

H

H H

C C

H H

H OH+p

H H

C C

H H

H H+

p



H

Br

H C C HH

H

H HC C

H H

H Br+

p

C CH H 1 Cl2+ p

C CH H 2 Cl2+ p

H H

C C

Cl Cl

Cl

Cl

H C C H

Cl

Cl



the replacement ( ) of a hydrogen on

an alkane or aromatic with (eg. F, Cletc)

3. Substitution Reactions

commonly used to make

Examples

organic halides

CH

H

H

H Cl ± Cl+ p

catCH

H

Cl

H H - Cl+

1.

substitution

another atom



Br ± Br+ p

catH - Br+

Br2.

I ± I + p

catH - I+

I

3.

4.

H

H

H

C C C

H

H

H

H

C

H

H

H H

Br

H

H C C C

H

H

H

H

C

H

H

Br2+ p

catH - Br+



the reaction of a with an

4. Esterification Reactions

Examples

carboxylic acid alcohol

1.

OHO

CH H

H

H

HO C+ p

H2SO4(aq)

O

O

CH H

H

H

C + H ± OH

the catalyst is sulphuric acid



p

H2SO4(aq)

OH

O

CCH C

H

H

H

H

+ C

H

H

HO C

H

H

H

2.

+ H ± OHC

H

H

C

H

H

HO

O

CCH C

H

H

H

H

Eli i i R i



an has water removed, forming an

plus the

5. Elimination Reactions

Examples

H

H

OH

H

H

H C C

1.

p

catH H

C C

H H

+ H ± OH

can react with ato produce an , a

and

alcohol alkene

waterorganic halides base(hydroxide) alkene

halide ion water



H

H

H

H

H

C C C C

HH

H

HOH

pcat

2.

H ± OH

H

C

H

C CH

H

C

H H

H

H +

3.H

H

Cl

H

H

H C C + OH p

catH H

C C

H H

+ H ± OH + Cl




CommonOrganic Reactions

1 C2H4(g) + H2(g) p C2H6(g)

2 C2H5OH(l) p C2H4(g) + H2O(l)

3 C6H6(l) + Br2(l) p C6H5Br(l) + HBr(g)

4 CH3COOH(l) + CH3OH(l) p CH3COOCH3(l) + H2O(l)

The esterification, addition, substitution and eliminationreactions respectively are ________, ________,

________, and ________.



a is a that forms

the for a polymer

6. Polymerization Reactions

a is a formed by the of

depending on the polymer,the monomers that makeit up can be or

monomer simple molecule

base unit

polymer very, very long molecule

covalent bonding

the same

different

bazillions of

monomers



polymers can be

eg)

natural

carbohydrates, proteins, DNA



polymers can be

eg)

synthetic

nylon, PVC, Teflon, polyester

l th t b h t d d ld d i t ifi



polymers that can be heated and molded into specificshapes are commonly called

the names of polymers are the monomer name within front

many have classical names instead of IUPA C names

plastics

³poly ́

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



Addition Polymers

formed when the electrons in double or triple bonds in

the monomer units are rearranged

the polymer is the formedonly product

Examples

H H

C C

H H

+

H H

C C

H H

p

cat

1.H

H H

H

C C C C

HH

HH n

polyethene

« «

2.



F F

C C

F F

+

F F

C C

F F

p

cat

Teflon

H Cl

C C

H H

+

H Cl

C C

H H

p

cat

3.

polyvinyl chloride (PVC)

F

F F

F

C C C C

FF

FF n

« «

H

H H

Cl

C C C C

ClH

HH n

« «

H

C C

H H

+

H

C C

H H

p

cat

4.

polystyrene (styrofoam)

H

H H

C C C C

H

HH n

« «



Condensation Polymers

polymerization reactions that involve the formation of

a (commonly ) as well asthe

each monomer must have functional groups

two common linkages formed:

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

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

small molecule waterpolymer

two

ester

amide

E l



Examples

1.

polyethylene terephthalate

PET

C Cpcat

CC OH

O O

HO

OHHO

H H

HH

+

n

······ CC O

O

O

O

C C

H H

HH

+H

2O

ester

linkage



p

cat

2.

CC H

O H

HO N

H

H

CC H

OH

HO N

H

H

+

n

······ + H2OCC

O H

N

H

H

CC

O H

N

H

H

protein

amidelinkage




R ow i ii

A. CH2

CF2

CH2

CF2

addition

B. CH2CF2CH2CF2 condensation

C. CH2!CF2 addition

D. CH2

!CF2

condensation

CH2 C CH2 C

F F

ÂÂÂ

F F

ÂÂÂ

Use the following information to answer the next question

The monomer for the polymer in the structural diagram above is

____i____, and it was produced by a _____ii____ polymerization reaction.

O Petroleum Refining



A lberta has vast reserves of petroleum in the form of

natural gas, crude oil and oil sand deposits

O. Petroleum Refining

most of this petroleum is refined and then burned as

petrochemicals are also used in the production of

fuel

plastics



refining of petroleum separates the crude mixture into

purified components is used to separate the

componentsfractional distillation

distillation works because of the differentof the components of crude oil boiling points

the the molecule and the the boiling point, the it rises in the tower

(asphalt, fuel oil, wax at bottom; gasoline at top)

lighter lower

higher

Fractional Distillation Tower



Fractional Distillation Tower

light hydrocarbons ± low molar

mass

heavy hydrocarbons ± highmolar mass

two types of reactions in petroleum refining:



two types of reactions in petroleum refining:

long chain hydrocarbons into

cracking requires heat and pressure

1. Cracking

there are many different types of cracking reactions,

forming different products (alkanes, alkenes)

eg) catalytic cracking, steam cracking, hydrocracking

hydrocracking requires

breaks smaller units

H2(g)



Examples

CH3 CH2 CH2 CH2 CH3 CH2 CH2 + H2(g)

cat

p

2.

CH3 CH2 CH2 CH3 + CH3 CH2 CH3

cat

p CH3 (CH2)6 CH3

1.

+ H2(g)CH3 (CH2)15 CH3

+ CH3 (CH2)7 CH3



small hydrocarbons are to make

2. Reforming

Example

requires heat and pressure

C7H16 + C12H26 p +C H H219 40

there are several types of reforming reactions

eg) alkylation to produce ³high octane´ gasoline

all reforming reactions produce

joinedlarger molecules

H2(g)

Examples



Examples

C7H16 + C12H26 p +C H H219 40

1.

2.

ethane + octane decane + hydrogen gas

organic notes 2011

Documents