Organic Chemistry Video 1

Organic chemistry is the chemistry of .

is the principle atom.

This is the chemistry of biological nature, both currently living and living.

Not all carbon containing molecules are organic. Two examples are:

1.

2.

Organic chemistry can also be called hydrocarbon chemistry because it focuses on carbon atoms bonded to

Nomenclature = Naming System

Formula

S t ruc tu ra l Formula

Condensed S t ruc tu ra l Formu la

Line D iagram

C2H6 e t h a n e

H H 1 I

H ~ C - C - H 1 I

H H

CH3CH3

o r CH3-CH3

Organic Chemistry Video 2- Aliphatics

ALKANES- Saturated hydrocarbons Nomenclature (Naming Rules)- end with "-ane" General Formula

CnH2n+2

Name rbons prefix Molecular

formula

1 Meth CH4 2 Eth C2H6 3 Prop C3H8 4 But C4H10

5 Penta C5H12

6 Hexa C6H14

7 Hept C7H]6

8 Oct

9 Non C9H20

10 Deca C10H22

The first 3 alkanes have no isomers (they can only be drawn 1 way).

H H H H H H

H - C - H H - C - C - H H - C - C - C - H I I I I I I H H H H H H

Isomers of Butane C4H10 Rule #1 -Name the longest continuous chain of carbon atoms (with group), and end it with -ane.

H H H H I • I I H - C - C - C - C - H I I I I

H H H H

Rule #2- Remaining side chains wi l l be given the ending -y l .

H

H - C - H

H - C — C " I I H H

H

- C - H I H

H

H ^ H

H H

C - i H

H

Organic Chemistry Video 3

Cyclic compoiiiids-Hydrocarbons in which the 2 ends of the chain are attached at the ends to form a ring The rule for naming is they all start with "cyclo-".

Name the carbon ring. Start it with "cyclo".

1,3- dimethylcyclopentane

C H -

H X

H

Halides-

Sometimes an organic compound will contain one or more halogen atoms.

Name the compound by using a prefix form for the halogen: fluoro, bromo, iodo, chloro.

Note which carbon has the halide if there is more than one C.

H I

H — C — F I H fluoromethane

CI I

H - C - O I

CI

H

CIS

r:l H

j : : : = C

H >:i

t r a n s

Organic Chemistry Video 7

Isomers of Pentane C5H12 H H H H H I I • I I

H - C - C - C - C - C - H I I I I I H H H H H H H

Rule #3- Multiple side chains wi l l use prefixes 2 is di- , 3 is tr i-, 4 is tetra- and so on.

H - C C C - C - H H I I I I

H H H H

H - C - H H H

H H H I H I I I

H - C - H h | ^ h

H - C C C - H H H H - C - H

H H

Isomers of Hexane C 6 H 1 4

H H H H H H I I I • I I

H - C - C - C - C - C - C - H I I I I • I

H H H H H H

H I H - C - H

H I H H H I I I I I H - C C C - C - C - H

I I I I I H H H H H

H I H - C -I

H

H I 'C' I H

H H - C - H

. C - C - C - H I I I

H H H

R u l e # 4 - G i v e t h e lowest number l o c a t i o n f o r e a c h s i d e c h a i n i f t h e r e is a n o t h e r p o s s i b l e l o c a t i o n i t c o u l d b e

l o c a t e d . G o b a c k a n d f i x t h e l a s t 2 i s o m e r s

H H - C - H

H I H H 1 1 I I

H - C C — C - C - H 1 1 I I

I H

Isomers of Heptane C 7 H 1 6

H H H H H H H I I I I I I • H - C - C - C - C - C - C - C - H I I I I I I I

H H H H H H H

H

H - C - H H I H H H H I I I I I I

H - C — C C - C - C - C - H I I I I I I H H H H H H

H

H - C - H H H I H H H I I I I I I

H - C - C C — C - C - C - H I I I I I I H H H H H H

H

H - C - H H I H H H I I I I I

H - C — C — C - C - C - H I I I I I H I H H H

H - C - H I H

H H I I H - C - C -I I

H H

H I H - C - H I H H I I I — C C - C - H

I H

H H I I

H - C - H H - C - H H H I I H I I I I I

H - C - C C C — C - H I I I , 1 H H I H H

H - C - H I H

H - C - H H - C - H H H I I H I I I I I

H-C'C—C C C - H

H I H H H H - C - H

I H

Rule #5- When there are 2 different side chains name them in alphabetical order usinj the carbon prefix (meth, eth..).

H

H - C - H

H - C - H H H I H H I I I I I

H - C - C C C - C - H I I I

H I H H H " I H - C - H

I H

Organic Chemistry Video 8

The rule for naming is they all end with "benzene". The general formula is C n H 2 n - 6 , n i s the number of carbons is used to determine the number of hydrogen atoms. Example n=8 soH=(2(8)-6)=10 Rule # 1 -Name the benzene ring. End it with "benzene". Rule #2-When necessary use the lowest number to give the locations of side chains that come off the benzene.

C6H6

H

H

C I

H

o

CyHn

o

Organic Cliemistry Video 9 A l c o h o l s - are compounds in which one or more hydrogen atoms in an all<.ane have been replaced by a hydroxyl ( -0H) group.

OH- is hydroxide, but in organic chemistty side chains end with - p i .

R - O H

Types of Alcohols Monohydroxy Alcohols- contains 1 - O H group

- C -I i I

C - C - c -I I

\ # I I

Primary Secondary Tertiary ihiiTiaryl i j - the C-OH is attached to one other carbon (on the end) Secondary!2'\l- the C-OH is attached to two other carbons [ertiaryi3 )- the C-OH is attached to three other carbons

Primary Example

H H H I t I H - C - C - C - O H

I I I H H H

Secondary I

H O H I I 1

H - C - C - C - H I I I H H H

I r I t

- C - O H - C - C - C

X H O H H I I I I

H - C - C - C - C - H • I I I H H H H

Tertiary Example

H O H I I I

H - C - C - C - H I H

I H

H - C - H I H

Organic Chemistry Video 10 Carboxylic Acids

Organic Acids- An organic acid is an organic Q compound wi th acidic properties. The most common 11

organic acids are the carboxylic acids whose acidity is R— associated wi th their carboxyl group -COOH.

iOlTieilclatlire -carboxyhc acids have an -oic acid suffix (e.g. octadecanoic acid)

Name Expanded Structure

O II

. C — O H H ^

o

H C - O H

H - C ^ I H

H H O • I II

H - C — C — C — O H I I H H

Name Condensed Structure

H C O O H C H 3 C O O H

C H 3 C H 2 C O O H

C 4 H 9 C O O H

CsHiyCOOH

Organic Chemistry Video 11 Esters

Esters (R-CO-O-R') are named as alkyI derivatives of

carboxyfic acids. The alkyI (R') group is named first

(the carbon chain f rom the alcohol). The R-CO-0 part

is then named as a separate word based on the

carboxylic acid name, wi th the ending changed f rom -

oic acid to "-oate".

I S n Ri ICA riON-is the general name for a chemical reaction in which two chemicals (typically an acid and an alcohol) form an ester as the

reaction product (water).

S y n t h e s i s - " W h e n a carboxylic acid and an alcohol react, a water molecule is removed, and an ester molecule is formed.

Nomenclature™

o I I

R-C 0-R,

O 0

R - C - O H + H - O R " > R - C - C ) R " +

Caiboxj'lic acid Alcohol Ester Water

O H H H , 1 1 I I I • I I I

H H

O H H II I I

H H c - 0 — C - C - H * • X I I

H - C - C ^ H H

H H

O H H It I I

H c^O^c^C^Vi \ * < I H

H H

Organic Chemistry Video 12 Aldehyde/Ketone/Ether/Amine

o Aldehydes-A compound wi th a carbon atom which is

bonded to a hydrogen atom and double-bonded to an oxygen a tom. This

is found on the end of the chain, ketones have this carbon In the middle

(no H either).

Nomenclature-The name is formed by changing the suffix -e of the

parent alkane to -al, so that HCHO is named methanal, and

CH3CH2CH2CHO is named butanal.

Expanded Structure

Name Expanded Structure Name

H O I II H - C - C — H I

H

H H ^

H - C - C - C - H • t H H

K e t o n e s - A compound with a carbonyl group ( 0 = C ) hnl^ed to two other carbon atoms in the chemical compound. The C = 0 is found somewhere in the middle of the chain (not the end). Three carbons are needed to form a ketone.

N o m e o c l a t l i r e - changing the suffix -e of the parent alkane to "-one"'

O

Name Expanded Structures Name Condensed Structures

H ° H 1 1

CH3COCH3

H - C - C - C - H 1 1 H H

CH3COCH2CH3

H 0 H H 1 II 1 1

H - C - C - C - C - H 1 1 1 H H H

CH3COCH2CH2CH3

H 0 H H H 1 II 1 1 1

H - C - C - C - C - C - H 1 I I I H H H H

CH3CH2COCH2CH3

C H 3 C O C H 2 C H 2 C H 2 C H 3

r . r U i N a chemica l c o m p o u n d whe re and D _ ^ — D

oxygen a tom connec ts two subst i tu ted g roups i 2

Nonie i lc la tLI re-Ethers can be named by naming each of the two carbon groups as a separate word followed by a space and the word ether.

Name Expanded Structure

H H I I H - C - O - c - H I I H H

H H H I I I H - C - O - C - C - H • I I H H H

H H H H I I I I H - C - C — 0 - C - C - H I I I I H H H H

C H 3 - C H 2 - O - C H 2 - C H 2 - C H 3 C H 3 - C H 2 - C H 2 - O - C H 2 - C H 2 - C H 3

\mines- ln amines , the hydrogen

a t o m s in the a m m o n i a have been rep laced one at a t ime by hydrocarbon g roups . On this page, w e are only look ing | at cases w h e r e the hydrocarbon g roups are s imple alkyI g roups .

R - N - R

R

H

N - C - H H H - C - H

H H

Petroleum Reactions Fractional Distillation- The various components of crude oil have different sizes, weights and boiling temperatures; so, the first step is to separate these components. Because they have different boihng temperatures, they can be separated easily by a process called fractional distillation.

Distillation of Crude Oil

1 L

m Fjira.;^

LesE: : - c , ' - i 40 Hydrocarbons with 1 to 4 carbon atoms

L 1 1 | P i_j ii

•j "Lh lilLp li-

i!_iLirai| l-J i-jj-

J IS tliLiu i_j iL

1

Fi J Jiiotialina iower

Hydrocarbons with 5 to 12 carbon atoms

Hydrocarbons with 12 lo 16 carbon atoms

:̂ - 360 C

Hvdr©«arfacitts wih '/ 15 to 18 carbon a»o«ss

- 370 c

Hydrocarbons with 16 io 20 carbon atoms

Greate? t han 3 7 0 C

fnore thars 20 carbon atoms

Types of Polymers:

1) Addition Polymers - formed by addition polymerization reaction: the monomer's double bond opens, allowing the monomer units to join end to end. The name of the polymer is found by putting a "poly" in front of the monomer's name. For example, propylene monomer forms polypropylene.

a) P o l y v i n y l C h l o r i d e 1. Formed from Vinyl Chloride monomer (chloro ethane) 2. The double bond breaks, and VC monomer units join end to end. 3. Used for water pipes, record albums, raincoats, shower curtains, wire insulation, vinyl siding

H H H H H H 1 1 1 1 1 1

H H H H H H I I 1 I 1 1

H 1

H 1

H 1

H 1 I I I I I 1

C = C C = : C C r ^ C 1 1 1 1 1 1

I 1 1 1 1 1

c = c c = c c = c I I 1 1 1 1

1

c = 1

1

C 1

1

C = 1

1

c 1 1 1 1 1 1 1

• H n H n H 1 1 1 1 1 1

n H • H • H 1

n 1

H 1

• 1

H V i n y l ch lor ide m o n o m e r s , separa te f rom each other

H H H H H H 1 1 1 1 1 1

H H H H H H I I 1 1 1 1

H 1

H 1

H 1

H 1 1 1 1 1 1 1

.c — c- c — c c — c 1 1 1 1 1 1

I I 1 1 1 1

• .c —c- -c —c- .c —c-I I 1 1 1 1

1

. c — 1

t C 1

1

•C — 1

1

C 1 1 1 1 1 1 1

n H • H • H 1 1 1 1 1 1 • H n H a H

i

• 1

H 1

n 1

H 2) A ca ta l ys t b reaks the doub le bonds , open ing up a free unpai red va lence e lec t ron on each C

H H H H H H H H H H H H H H H H I I I I I I I i I I I I I I I I

H — C — C — C — C — C — C — C — C — C — C — C — C — C — C — C — C — H I I I I I I I I I I I I I I I I

a H C i H C T H n H n H a H n H n n 3) The v inyl ch lor ide r-nonomers j o i n end to end. The react ion is t e rm ina ted by the addi t ion of hyd rogen g a s , which adds on to the end of the polyv iny l ch lor ide m o l e c u l e , s topp ing any fur ther p o l y m e n z a t i o n .

b) P o l y s t y r e n e

1. Formed from styrene monomer (phenyl ethane, basically ethene with a benzene attached to it) 2. The double bond breaks, and styrene monomer units join together. 3. Used for plastic model kits, styrofoam

n number of s ty rene m o n o m e r uni ts comb ine toge the r to forr"n a cha in of sy rene m o n o m e r s n un i ts long. If you start w i th 2 0 0 0 s ty rene m o n o m e r un i t s , the po l ymer Wi l l be 2000 uni ts long.

c ) P o l y t e t r a f l u o r o e t h e n e ( tef lon) 1. Formed from tetraflouro ethene monomer 2. The double bond breaks, and TFE monomer units join together. 3. Used for no-stick pans. 4. Accidentally discovered in 1938 by Roy Plunkett.

F \ n u rn b e r of TP E m o n o rn e r u n it s c o rn b i n e t o g et h e r t o I form a chain of TFE r"nonnrner n units long. If you start I ' with 1500 TFE rnonomer units, the poIyrner wilI be jr /' 1500 units long.

H H I I C = C

A L

H H \ I I ' C — C —

F F I I

n C = C I I F F

C — I F

©2011, Mark Rosengarten AE 20

2) Condensation Polymers - formed by dehydration synthesis of difunctional monomer units. H and OH are removed from the ends of the monomer units, allowing them to join together. Water is given off as a byproduct.

P o l y e s t e r

1. Formed from monomer units that have an alcohol functional group on one end and a carboxylic acid functional group on the other end. 2. The opposing ends undergo dehydration synthesis, and form the polymer.

H 0 H 1

0 H O H O H O II 1 II 1 II 1 II 1 II

HO— C — C — O H + H O -1

- c -1

- C - O H + H O - C — C — O H + H O — C — C - O H + H O - C — C — O H 1 1 1

1 H

1 H

1 1 1 H H H

The m o n o m e r s above lose po lyes ter , n-1 V'/ater is Io

H O H O 1 I I 1 I I

H and O H and bond toge ther th rough dehydra t ion s y n t h e s i s to fo rm zA, because only the H's and OH's betV ' / een the rnonomer uni ts are lost .

H O H O H O 1 II 1 II 1 II

1 II 1 II HO— C — C — 0 - C — C

1 1

— 0 — C — C — 0 - C — C — 0 — C — C — O H + 4 H2O 1 1 1

1 1 H H

1 1 1 H H H

H 0 1 11

n H O - C — C — O H — 1

-> / H 0 \

1 1 II '1 < - -gene ra l to rmula for the fo rmat ion H O f C - C - 0 - 1 - H + n-1 H2O of po l yes te r

1 H

3) Rubber

a) cis- Polyisoprene (tires), polybutadiene (tires), polychloropropene (Neoprene...wire covering, automotive drive belts, wetsuit material)), Nitrile (automotive hoses and gaskets)

1. Formed by addition polymerization

2. The resultant macromolecule is tacky and not very strong. It generally has a low melting point.

3. In order to make this stuff serviceable, it must by toughened up. This is done by a process whereby the polymer chains are cross-linked with sulfur. This toughens up the rubber. This process was discovered accidentally by Charles Goodyear in 1839. This process is called v u l c a n i z a t i o n . Unfortunately, when heat is applied to rubber so treated, it does not melt, but burns, releasing CO, CO2 and S02.

addi t ion of sulfur

V \ . / \ V ' \ \

S A

V v s V

s

/ \ / • • • • : / • • : . , - ' ' \•• \ . . ' \....-' X...-' - v - \ . - \ . - \

s s / \.'' \/ \/ \y v \y \/ \

s s

s 5 5 A ,

•-../ - v - w - ••-•y V \ ; s s s

.-x A. / x ..x. A V

V ' \y ••••

Natura l po l ybu tad iene rubber: the po l ymer s t rands are separa te f rom each other, m a k i n g the rubber soft and t a c k y , . . n o t at all su i tab le for t i res or h o s e s or be l ts .

The s t rands are now c ross - l i nked w i th sulfur a t oms . This m a k e s it a lmos t imposs ib l e for the s t rands to move past each other. Th is vu l can ized rubber is e:;;tremely tough and durable and perfect ly su i ted for the r igors of the road.

2011, Mark Rosengarten AE 21