Addition rxn Alcohol Aldehyde Alkane Alkene Alkyne Amide Amine Amino acid Dehydration synthesis Ester Unit Vocabulary: Esterification Ether Fermentation Functional group Halide (halocarbon) Hydrocarbon Isomer Ketone Monomer Organic acid Organic chemistry Polymer Polymerization Primary Saponification Saturated hydrocarbon Secondary Substitution rxn Tertiary Unsaturated hydrocarbon Unit Objectives: 1. Identify organic compounds versus inorganic compounds based on structure, name, or characteristics of an unknown compound 2. Recognize the characteristics of organic compounds 3. Differentiate between aliphatic, aromatic, saturated, and unsaturated compounds Name organic compounds based on lUPAC rules, with the help of table P and Q 4. Draw organic compounds from a lUPAC name 5. Distinguish between alkynes, alkenes, and alkanes Name and identify isomers 6. Identify various functional groups of organic compounds using Table R: Halide (halocarbon) o Organic Acid Alcohol o Ester Ether o Amine o Aldehyde o Amide o Ketone Categorize various organic reactions properly including addition, substitution. o o o polymerization, esterification, fermentation, saponification, and combustion. 1
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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