Add i t i on r x n
Alcohol
A ldehyde
Alkane
Alkene
A lkyne
Amide
Amine
Amino acid
Dehydrat ion synthes is
Es te r
Unit Vocabulary:
Es t e r i f i c a t i on
E the r
Fe rmenta t ion
Functional group
Hal ide (halocarbon)
Hydrocarbon
I s ome r
Ketone
Monomer
Organic acid
Organic chem i s t r y
Polymer
Polymer izat ion
Pr imary
Sapon i f i ca t ion
S a t u r a t e d hydrocarbon
Secondary
Sub s t i t u t i o n r x n
T e r t i a r y
Unsa tu ra ted hydrocarbon
Unit Object ives:
1. I d e n t i f y organic compounds versus inorganic compounds based on s t r u c t u r e , name,
or cha ra c t e r i s t i c s o f an unknown compound
2. Recognize t h e cha r a c t e r i s t i c s o f organic compounds
3. D i f f e r en t i a t e between al iphatic, aromatic, sa tu ra ted , and unsaturated compounds
Name organic compounds based on lUPAC rules, w i th t he help o f table P and Q
4. Draw organic compounds f r o m a lUPAC name
5. Dist inguish be tween alkynes, alkenes, and
alkanes Name and i d e n t i f y isomers
6. I d e n t i f y var ious f unc t i ona l groups o f organic compounds using Table R:
Hal ide (ha locarbon) o Organic Acid
Alcohol o Es te r
E t h e r o Amine
o A ldehyde o Amide
o Ketone
Categorize various organic reactions properly including addit ion, subst i tut ion.
o
o
o
polymerization, es te r i f i ca t i on , fe rmentat ion , saponif icat ion, and combustion.
1
I . Organic Chemistryi t h e s tudy o f compounds t h a t conta in CARBON
I I . Properties of Organic Compounds A. Mos t l y nonpolar
B. So lub i l i ty: most a r e INSOLUBLE in wa te r
a. L IKE D ISSOLVES L IKE
C. Conduct iv i ty:
a. most ly N O N CONDUCTORS (s), (I), A (aq) s t a t e s
b. Only ORGAN IC A C I D S I O N I Z E in so lut ion = POOR CONDUCTORS
D. Me l t ing/bo i l i ng points:
a. WEAK IMF ' s ^ LOW MP's/BP's
E. React iv i ty Rate:
a. REACT SLOWLY
i. covalent molecules t end t o have re l a t i ve l y H I G H # OF BONDS ->
MORE STEPS in reac t ion -> r x n t akes longer
I I I . Bonding
A. Carbon has 4 VALENCE ELECTRONS and can f o r m 4 bonds
B. These 4 single bonds spread out evenly t o c r e a t e a TETRAHEDRAL molecule
( l ike a t r i p o d )
(on paper, 2-
2
C. Carbon a toms S H A R E E L E C T R O N S w i t h o t h e r carbon atoms, f o rm i ng C O V A L E N T
C H A I N S , R I N G S , and NETWORKS ; C\\<x\x\s of carbon atoms can be open or closed, or
even fo rm three-dimensional networks.
GH3-<:%C;HJ-Q-CH
D. S A T U R A T E D HYDROCARBONS - all S I N G L E BONDS be tween carbons
{N^AXmUl^ number o f HYDROGENS a t t a ched )
a. When 1 pair o f e lec t rons is shared between two carbon atoms t h e bond is
cal led a single covalent bond.
E. U N S A T U R A T E D HYDROCARBONS - a t least one MULT I P LE BOND in carbon
chain
a. I f carbon atoms share two pairs o f e lec t rons t h e bond is cal led a double
covalent bond. t t
b. Carbons can even share th ree pairs o f e lec t rons . This bond is cal led a triple
covalent bond.
t
IV . Types Of Chemical Formulas
A. Molecular Formula: shows t h e # d F A T O M S o f each ELEMENT in a compound;
least i n f o rma t i v e f o rmu la
B. St ructura l Formula: shows t h e # OF A T O M S o f each ELEMENT A N D t h e
ARRANGEMENT o f t h e ATOtAS: most i n f o rma t i v e f o rmu l a
C. Condensed Formula = C O M B I N A T I O N o f b o t h STRUCTURAL and
MOLECULAR formulas; each carbon is w r i t t e n w i t h i t s cons t i t uen t hydrogens
fo l lowed by t h e proper subsc r ip t
C . \ 2 lr̂ V ^
Mcl hane Ethane
Molecular Formula C
Structural Formula -< "V,
\
I ^
- c -
1 \
Condensed Formula
\
Ball-and-Stick
Model
Space-Filling Model
4
V. H0M0L060US S E R I E S of Hydrocarbons
rA. a group o f R E L A T E D CONiPOUms in
which each member d i f f e r s f r o m t h e one
b e f o r e i t by O N E CARBON U N I T
B. Th ree Groups:
a . Alkanes:
Table Q Homologous Series of Hydrocarbons
1 General Fonmila
Examples 1 General Fonmila Name S trucl iiral Ft»rimila
a kunes ethane H H 1 1
H—C—C-H I 1
I I H
al kenes ethene n H \c=c
a] kynes eth)iie H - C s C - H
. hydrocarbons w i t h single covalent bonds
. general fo rmu la= ^ h \ A x y ^ V
. example:
n = number of carbon atoms
Y iv. fo l l ows lUPAC naming rules-name ends in-.
V. shows isomer ism s t a r t i n g w i t h J;^ member o f t h e ser ies
. hydrocarbons w i t h double covalent bonds
b. Alkenes: — ^
. i f you have 2 double bonds, i t is cal led a _
. general f o r m u l a = _ C
iv, example: CL:)^'\(/
V. fo l l ows lUPAC naming rules-name ends in-.
v i . shows isomer ism s t a r t i n g w i t h M memper o f t h e ser ies
c. Alkynes:
i. hydrocarbons w i t h t r i p l e covalent bonds
. general f o rmu la= ^
. example:
r ^
Jv. follows lUPAC naming rules-name ends in- \^
V. shows isomerism starting with _i member of the series
V I . Structural Formula:
A. S t ra ight Chains: also r e f e r r e d t o as n-alkanes ("normal" alkanes); n-alkenes, n-alkynes
B. Branched: not a s t r a i g h t continuous chain; organic molecule t h a t has smal ler branches comi
o f f a longer cont inuous chain
example:
V I I . Nomenclature (TUPAC Naming):
A. S t ra igh t Chains of Hydrocarbons
a. p r e f i x e s (Tab le P)-dependent on t h e number o f C's
b. s u f f i x e s (Tab le Q) -dependent on t h e t ypes o f bonds
example:
c c
6
B. Branched Hydrocarbons
a. t h e r o o t name is t h a t o f t h e longest continuous chain o f C a toms (aka: main chain)
b. any branches o f f t h e main chain a r e called subs t i t uen t s
c. t h e main chain is numbered so t h a t t h e subs t i t uen t s rece ive t h e lowest possible
numbers
i. each subs t i t u en t rzcev^zs a name and a number t o locate i t
1. p r e f i x corresponds t o number o f carbons (Tab le P)
2. su f f i x -a lways " - y l "
i i . s ub s t i t uen t s a re l i s ted in a lphabet ica l o r de r
i i i . when more than one o f t h e same subs t i t uen t is p resen t use t h e appropr ia te
p r e f i x (d i=two, t r i = t h r e e )
d. Unsa tu ra ted Hydrocarbons
i. t h e double or t r i p l e bond must be included in t h e main chain.
i i . when number ing w i t h subs t i t uen t s , t h e bond ge t s t h e lowest possible number.
Example 1:
Example 2:
V I I I . Drawlnq Structural Formulas of Hydrocarbons:
/Alkanes: Example: Pentane
1. De te rm ine t h e number o f carbons and draw
t h a t many in a row
2. Because t h e molecule name ends in -one you
know t h a t t h e r e a r e only single bonds. Connect all o f t h e carbons w i t h a single line.
3. Each carbon a t om must have 4 bonds connected t o i t . Add enough hydrogens so t h a t
each carbon has 4 t o t a l bonds connected t o i t .
4. Use t h e molecular f o rmu la t o make sure t h a t you have t h e c o r r e c t number o f
hydrogens.
Draw t h e s t r u c t u r a l f o rmu l a f o r propane:
Alkenes: Example:-a'Perilene
1. De te rm ine t h e number o f carbons and draw
t h a t many in a row connected by a single line.
2. Because t h e molecule name ends in -ene you
know t h a t t h e r e is a double bond. The name o f t h e molecule wi l l t e l l you where t h a t
bond is located. For example, 2-butene wi l l t e l l you t h a t t h e r e a re 4 carbons and t h e
double bond is located a f t e r t h e second one. Add another l ine f o r t h e double bond.
3. Each carbon a tom must have 4 bonds connected t o i t . Add enough hydrogens so t h a t
each carbon has 4 t o t a l bonds connected t o i t .
4. Use t h e molecular f o rmu l a t o make sure t h a t you have t h e c o r r e c t number o f
hydrogens.
r a w t h e s t r u c t u r a l f o rmu l a fo/^htxem:
Alkynes
1. fo l low t h e same ru les as alkenes, excep t t h e r e is a t r i p l e bond, not a double bond.
Draw t h e s t r u c t u r a l f o rmu l a f o r 2-but^fne:
I X . Isomers
H H H H H H H 1 ( 1 \ 1 II
- c - - c - -C—H H-C—C—C—H 1 \ f 11 A l!
H H H H H H H—C—H
1 H
As t h e number o f carbon atoms increases, -the number o f possible i somers increases.
The l e t t e r /? b e f o r e t h e name o f a hydroca rbon s ign i f ies t h a t i t is t h e normal , or s t r a i gh t chain
isomer. Branched isomers must have d i f f e r e n t names.
Naming Isomers; The ru les f o r naming organic compounds a re governed by t h e In te rna t i ona l
Union o f Pure and Appl ied Chemis t ry ( lUPAC) .
9
Procedure'.
1. Find t h e longest cont inuous chain o f carbons and use i t s nan\ as t h e base. (Example: 4 carbons
- butane)
Z. Count t h e number o f carbons in t h e s ide branch and
assign a p r e f i x based on t h e name o f t h e corresponding
alkane.
(Example: 1 carbon = methane = methyl)
Alkane A Iky 1 Group
Methane Methyl
Ethane Ethyl
Propane Propyl
c - c - c - c I c
c - c - c - c I c -butane
c - c - c - c
c methylbutane
- - - c-
2-methylbutane
3. I f necessary, t h e locat ion o f t h e s ide branch (alkyI group) is shown by assigning numbers t o t h e |
carbons in t h e longest chain. Number ing should begin a t t h e end t h a t has t h e side chain a t t a ched
t o t h e lowest number possible. (Example: Z-methylbutane, not 3-methyl butane)
4. I f more than 1 s ide branch is a t t a c h ed commas a re used t o CH3 I
s epara te t h e numbers in t h e name and p r e f i x e s a re used t o deno te more C H 3 - C H 2 - C - C H 3
than one o f t h e same group, such as 2,2-d imethy lbutane:
( I - c - c c -
1
10
b o
X. Functional Groups - Tab le R
rganic compounds in which one or more hydrogen atoms of a hydrocarbon are replaced by
other elements
Halocarbons (Hal ides)
- Organic compounds in wh ich one or more hydrogen a toms a re replaced by a halogen
(Group 17 e lement)
- Naming -> Same as hydrocarbons, bu t add a p r e f i x t o s i gn i f y which halogen is
a t tached .
Br H H Br H I I I f !
, H-C—C —C—C—C-H Example: \
H H H H H
- 5 carbons, s ingly bonded = P ^ ^ V̂ K̂̂
- Bromine is p resen t on t h e \t and carbons.
- The r e a r e 2 , Bromines.
- We l l , t h e f i r s t ha l f would be named 1, 4 - d ib romo ^
- The f i na l name is t
Name t h e fo l lowing halocarbons:
3 ^ 1
H F H F a I I I I
1 I I I H H H H
b. 0 % - C H - C H - C H 2 - C H 3
F CI
11
Alcohols
- Organic conr^pounds in which one or nr^ore hydrogen atoms a re replaced by an
-OH group. (No more than one OH can be a t t a c h ed t o a carbon)
- They a re no t bases! (Do not f o r m -OH ions in aqueous solution!)
- Naming Same as hydrocarbons, bu t d rop t h e "e" ending and add "o l "
(For example: methano l , 2 ,2 -d imethy lbu tano l . . . )
Primary alcohols
One -OH group is a t t a ched t o a carbon on t h e end o f a chain.
Represented by R-OH, where R is a hydroca rbon chain o f any length
Typical example =
1 ca rbon -OH
Name t h e fo l l ow ing alcohols:
a. CH3CH2OH
Secondary Alcohols:
CH3OH
/ b. m^CHgCH^OH propc^no
One -OH group is a t t a c h ed t o a secondary carbon a tom. (A carbon a t t a ched t o 2
o the r carbons)
12
Tertiary Alcohol:
One -OH is a t t a c h e d t o a t e r t i a r y carbon a tom. (A carbon a t t a ched t o 3 o t he r
carbons)
H CH. 1 1
CH3CH2CH2~C—OH C H 3 C H 2 — C — O H C H 3 - - C — O H
H H CH3 l-Rnfanol 2-Rnianol Mftthvl-2-nmnanol
(a primary alcohol) (a secondary alcohol) (a tertiary alcohol)
* Alcohols can also be c lass i f i ed by t h e number o f hyd roxy l groups a t t a ched t o t h e carbon
chain.
Pi hyd roxy (2 - OH's) and T r i h i d r o x y (3 - OH's) Alcohols conta in 2 and 3 hyd roxy l groups, j u s t
t h e i r names s ta te . OH OH
H - C — C - H I I H H
1,2,*ethanddiol
OH OH OH
H-C-—C—C-H I I I
H H H t,2,3>propanetrlor
Draw the followino molecules:
1. 2-chloro, 2-propanol
o n
C i
2. 2 - f luoro , 1,2-butanediol
1+
c c - c
13
The Carbonyi Group
One o f t h e most func t iona l groups in chem i s t r y , which consists o f a \ ,C= 0
carbon a t om connected t o an oxygen a tom by a double bond.
A f am i l y o f organic compounds contain ing t h e func t iona l group - COOH.
Organic acids a r e f o r m e d by.
1. Dropping t h e f ina l "e" o f t h e alkane member.
2. Replace t h e V w i t h olc" .
3. Then add t h e word "ac id" .
Example: Me thane Methano ic Ac id Ethane Ethanoic Ac id
0
QH OH
Name t h i s ac id:
OH
O
14
Aldehydes OJ^cA p ^ ^ ^ f r u ' < x h ^ ^ ^
- The carbon o f t h e carbonyl group is bonded t o a t least one hydrogen atom.
- Named by adding t h e s u f f i x " - a l " t o t h e name o f t h e paren t hydrocarbon.
R
H
H > . o
H
CH,
H aldehyde methanai
Name t h i s a ldehyde;
C H 3 — C H 2 p H
Ketones
- Has no hydrogen atoms d i r e c t l y a t t a ched t o t h e carbonyl group
- Named by adding t h e s u f f i x "-one" t o t h e name o f t h e paren t hydrocarbon.
c = o CH3
CH3 ketone propanone
Name t h i s ketone:
CH3—CHj—C O
0 I I
CK3
I
/
1 15
b o
Es t e r s O
Made f r o m an organic acid and an alcohol, resu l t ing in: R c O R
Naming use t h e names o f t h e component alcohol and
ac id and add t h e s u f f i x -oa te .
Have s t r ong aromas; responsib le f o r t h e odors o f many foods and
f l avo r i ngs
Example: .0
C H 3 C H 2 — G , = Methy lp ropanoa te
Ethers
0 - C H 3
- General f o rmu la Ri - O - R2 whe re each R rep resen ts a carbon chain
- Commonly named by naming t h e two branches f i r s t and adding t h e word
" e t he r "
H H H H
Examples H — c — c — o — c — c — H ~ d'^f^yl e t h e r
H H H H
Name t h i s C H 3 - C H 2 — 0 - C H 3
e the r :
Ah4
-^vFormed when 1 or more hydrogens in ammonia (NHs) are rep laced
by an a lkyI group
R
R
N
- Named by changing t h e -e ending o f t h e alkane name t o -amine and adding
a number t o show t h e locat ion o f t h e amine group 16
H30 V Example: N - H = d imethy lamine
Name t h i s amine: H
H - C - N 1 \
H
H
H
Amides
o
Basically organic acids whe re t h e -OH is rep laced by an amine R —
group ^-^2
- Named by changing t h e -e ending o f t h e alkane name t o -amide
and adding a number t o show t h e locat ion o f t h e amine group
Example: q = e thanamide
NH2
Name t h i s amide: v O r 6 | ^ 0 v ^ q i ^ i c { e_
CH3CH2— 3SfH2
17
XI.Organic Reactions-
C O M B U S T I O N
- When s a t u r a t e d hydrocarbons ( l i ke methane) r eac t w i t h oxygen a t a high
t e m p e r a t u r e t h e y produce carbon d iox ide and wa te r - comp le te combust ion
CH4 + 2O2 ^ CO2 + 2H2O
- I f t h e r e is i n su f f i c i e n t oxygen, carbon monoxide is produced - incomplete
combust ion.
2CH4 + 3 0 2 - ^ 2CO + 4H2O
W r i t e t h e balanced reac t i on f o r t h e complete combust ion o f propane:
S U B S T I T U T I O N R E A C T I O N
- The rep lacement o f one kind o f a t om or group by ano the r k ind o f a t om or group
- An example o f t h i s occurs in s a t u r a t e d hydrocarbons whe re a hydrogen is
replaced.
- I f t h e hydrogen is rep laced by a halogen (F,CI, Br, I , A t ) ha logenat ion is said t o
have occu r red . H H H H Heat or light
H — C — C — H + C I — C I I I H H
> H — C — C — C I + H — C l I I H H
Name these compounds
18
H H
Ethene Chlorine
H H I I
H - C ~ C ~ H I I
CI CI
1, 2-Dichloroethan© A D D I T I O N R E A C T I O N
- The adding o f one or more a toms or
groups a t a double or t r i p l e bond.
- The double or t r i p l e bond is changed t o a single ( s a tu r a t ed ) bond or double bond.
- I f hydrogen is added, t h e process is r e f e r r e d t o as hydrogenation. Th is react ion
is done on unsa tu ra ted hydrocarbons , such as vegetab le oi ls, t o make t h e oils
so l i d i f y a t room t empe ra tu r e : s a t u r a t e d f a t s t end t o be sol id a t h igher
t empe ra t u r e s t han ^ ^
unsaturated fats. H
Name these compounds:
H
V
a
E S T E R I F I C A T I O N CH3
H I C == O esterification
hydrolysis
CH3 H I
H-C—O ; c=o
H alcohol
H acid ester
+ H2O
water
Organic ac ids (COOH) r eac t w i t h alcohol's t o produce an e s t e r plus water.
The process is reve rs ib l e and slow: E s t e r i f i c a t i on = acid + alcohol <r-^ e s t e r +
wa te r
E s t e r i f i c a t i on is also r e f e r r e d t o as a hydrolysis (adding w a t e r ) and is
cons idered t o be a dehydration react ion (removing w a t e r ) o r condensation
(wa te r p roduc t ) . ^
Name these
compounds:
CH^q0H4-ha0CH^CH, J Z l CH3COCH2CH3 + H2O
wate r
19
S A P O N I F I C A T I O N
- The hydro lys is o f an e s t e r such as f a t w i t h an inorganic base t o produce an
alcohol and a soap.
B&l
F E R M E N T A T I O N
- Chemical process where molecules a re broken down.
- For example, zymase, an enzyme (which ac t as ca ta lys t s ) f r o m yeast , breaks
down glucose t o f o r m ethano l ( t h e alcohol we d r i nk ) and carbon d iox ide
(carbonat ion.)
y ^ t enzymes C^E^P^ >2C^EpE + 2CO2
glucose ef&anoi cariioii dlf̂ dde
P O L Y M E R I Z A T I O N
- A polymer is a large molecule composed o f many repeat ing un i t s cal led monomers,
- I n po lymer izat ion , a number o f smal ler monomers j o i n t o f o r m a larger polymer.
- Natural polymers: p ro te ins , cel lulose, s t a r ch
- Synthet ic polymers: po lyethy lene, nylon and po lyester .
20
C O N D E N S A T I O N P O L Y M E R I Z A T I O N
- Monomers a re j o i ned by a dehyd ra t i on reac t ion o f two alcohols whereby
wa te r is re leased and an e s t e r linkage is f o r m e d .
H H H H H H H H
H O - C - C - 0 ( H + H ^ C - C - O H - H O - C - C - 0 - C - C - O H +HiO I i I I I I I I ^
H H H H H H H H monomer monomer dimer water
This wi l l cont inue t o grow as addi t iona l monomers a t t a c h t o t h e d imer.
Polyester is f o r m e d t h i s way.
A D D I T I O N P O L Y M E R I Z A T I O N
- Jo in ing o f unsa tu ra ted monomers t o f o r m long chains
- The double or t r i p l e bonds a re reduced t o single o r double bonds j u s t l ike we
learned ear l i e r in add i t i on react ions.
n
H \ . C = C
\ H/
n unite of ethene
addition
/ H H \ I I
^ H H polyethylene
The l e t t e r n is used t o denote t h a t t h e monomer un i t repeats .
21
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