ii Iii nil

_______________
____________
Cr[: Form WS11.3.2A
Name
ORGANIC CHEMISTRY Date
Period
Waiiit Har11$
A substituted hydrocarbon is a hydrocarbon with an
element other than hydrogen attached somewhere along
the hydrocarbon chain. It is named in a similar fashion to
a hydrocarbon. This can be illustrated with alcohols as an
example. The compounds pictured to the lower left are
alcohols. They look like alkanes
H with —OH at one end where a
I hydrogen would have been. The
H—C—j--OH
—OH is called a functional group.
H The rest of the molecule is called a
H H residue (R). The general formula
for alcohols is R—OH. CH3OH, the
H—C—COH first alcohol pictured to the left is
formed by substituting an —OH
H H
group for hydrogen on methane
H H H
I I I
(CH
H—C—C—C—--OH
R—-OH
CH3CH2CH2OH is 1-propanol.
4). As a result, it is called 1-
methanol. The suffix ol shows that
it is an alcohol. The root met/ian
comes from methane. The number
1 shows the location of the —OH.
The next alcohol in the series,
CH3CHOH, formed from ethane,
is called 1-ethanol.
The alcohols and several other classes of substituted
hydrocarbons are found in Table R. The root is determined
by counting the number of carbons in the chain. For
halides, the substitution is identified with a prefix. For the
remaining substitutions, a suffix is used. (See Table R.) As
with all hydrocarbons, the number and location of groups
needs to be identified.
ii Iii
H—C—C—C—H
I ,2,2-trifluoropropane
3
1.CH3CH,CHOHCH
nil
H—C—C—C—C—H
2-butanone
Table R
Organic Functional Groups
CIas of Funcdonal General
Compound Group Formula Example
—F(fluoro-) R—X
halide — Cl (chioro-) (X represents CH3CHCICII
(hakicarbon) — Br (bromo-) any halogen) 2-eblorepropane
-I (iodo-)
alcohol —OH R011
ether —0— R—O—R’
3
2OH
CH3CH,,UI
1-propanol
2CH3
CH3OCI1
methyl ethyl ether
0
0 0
II
aldehyde It II CH3CH2C—H
—C—H R—C—H
propanal
0 0 0
ketone II II
—C— R—C—R’ CH3CCHCH
2-pentanone
2CH3
0 0 0
organic acid It II
II
—C—OH fl—C—OH
propanoic acid
CH.CH
2C—OH
0 0
0
II
ester II II CNCHCOCH
—c—o— R—c—o—ir
methyl propanoate
amine
— N—
ir
CH3CYJ
2
2CHaNH
B—N—fl” 1-propanamine
0
0 OR’ It
amide It I II I
—C—NH fl—C—NH
CH3CHaCNH
popanamide
2
Name the following compounds using the rules for naming hydrocarbons and by referring to the reading and Table
R above.
2. H——!!—J—H
H
H
Continue ir

________________
eitrf: Form WS 11 . 3 . 2A
Naming Substituted Hydrocarbons
ORGANIC CHEMISTRY Page 2
3. H___J—!!—OH
H
2CH3
4.CH3CH2CH2OCH
5. CHOCH
6. H_L_i4__O—_J,_H
H H H
0
II
7 CH3CH2CHCH
8.CH3CH2CH2CHOHCH
2CH2CH2CH3
9. CH3CHO
2CH,CH
10.CH3CH2COOCH
2CH3
11. H—i—J——OH
12. CC1
4
H
H
13. CF,CH,
0
14. HC—O—CH
3
2CH3
15.CH3CH2OCH
2CH2CH2OH
16.CH3CH2CH,CH
17.CH3CH,CHOHCH2CH2CH3
2CH2CH2CHO
18.CH3CH2CH2CH,CH
2CH2CH2CH2CH3
19.CH3CH,CHBrCH
3
2CH,CFI
20.CH3CHNH
© Evan P. Silberstein, 2003

to describe common reactions of organic compounds
5:rajjc aci@i
__
triple bonds)
* Definition -
of hydrogen to an alkene or an
alkyne (or other carbon compounds with double or
\ / II
/ \
CC + Br
2 — H-C-C-H
H H HH
* Addition
* halogenation -
* Definition = Adding two or more atoms to carbon at a
* Characteristics
* Examples
* take place more easily than substitutions
* unsaturated bonds are more reactive than saturated
* results in the formation of a single product
bonds and alkynes are more reactive than alkenes
point of unsaturation
ane + bromine —, monobromoethane + hydrogen bromide
eth
H—C——C—H + Br
* example: halogen substitution
* with insufficient oxygen —‘ CO and water
* example: C2H8 + 502 3CC, + 4H20
—‘ * example: 2C3H, + 702 6CC + 8H20
- * Substitution
with sufficient oxygen —‘ CO2 and water
* Combustion -
burning
replacement
Ill
I II
H H H H
occurs
addition
* Hydrogenation
H H BrBr
at room temperature
2 H—C—C—H + HBr
of hydrogen in saturated
Some reactions of hydrocarbons
hydrocarbons
ebrf: Form Lsll.4A Name
ethylene monomer polyethylene
n
(
* Esterification -
glucose — ethanol + carbon dioxide
C6H12 06 ““ > 2C2H50H + 2C0
* Fermentation -
2
* fruit flavorings and aromas
* lipids are formed by esterification of glycerol by
* Polymerization -
* importance:
* General formula: RCOOR
* Formation: ROH + RCOOH - RCOOR + H2O
* produces organic salts called soaps
* forms glycerol as a byproduct
* Saponification -
fatty acids
breakdown of organic molecules
during anaerobic respiration
enzymatic
formation
hydrolysis
formation
H H II H H H H H
II II II II
HH)
* the process can be repeated to form long chain
* examples: vinyl plastics - polyethylene, polystyrene
(--)n
H\_/H
* condensation polymers must have at least two
monomer monomer
j1 )i 11
OH—C—C—OH OH—C—C—OH —- OH—C—C—O—C—C—OH
* Polymer - large molecule formed from many smaller,
* Condensation - joining monomers by dehydration
* Addition polymerization -
involves
I I
and triple bonds of unsaturated hydrocarbons
* examples: silicones, polyesters, polyamides,
of fats by bases
repeating units of smaller ones
repeating units or monomers
synthesis
polymers
phenolic plastics, and nylons
of esters
of large molecules from
functional groups
opening up double
dimer
ORGANIC CHEMISTRY Date Period

zrf: Form Nll.4A
ORGANIC REACTIONS
ORGANIC
CHEMISTRY
Page 2
Answer the questions below by circling the number of the correct response
1. One of the products produced by the reaction betweenCH3COOH
and CH3OH is
(1)HOH
(3)HCOOH
(2)H2S0 4 (4)CH3CH2OH
2. A fermentation reaction and a sponification reaction are similar in
that they both can produce
(1) an ester (3) an acid
(2) an alcohol (4) a soap
3. The product of a reaction between a hydrocarbon and chlorine
was 1,2-dichloropropane. The hydrocarbon must have been
(1)C 5H10 (3)C
(2)C2H4
(4)C4H8
3H6
4. The product of a reaction between a hydrocarbon and chlorine
was 1 ,2-dichloropropane. The hydrocarbon must have been
(1)C 5H10 (3)C
(2)C2H4
(4)C4H8
3H6
5. The reactionC3H6 + H2 —C3H8 is an example of
(1) substitution (3) polymerization
(2) addition (4) esterification
6. The reactionC2H4 + H2 —‘C2H6 is an example of
(1) addition (3) saponification
(2) substitution (4) esterification
7. A reaction between an acid and an alcohol produces an ester and
(1) carbon dioxide (3) glycerol
(2) water (4) ethanol
06
8. The fermentation ofC6H12 will produce carbon dioxide and
(1) a polymer (3) an ester
(2) a soap (4) an alcohol
9. The reaction:C4H8 + Cl 2 —C4H8CI is an example of
(1) substitution (3) polymerization
(2) addition (4) fermentation
2
10. A reaction betweenCH3COOH and an alcohol produced water
and an esterCH3COOCH Which alcohol was used in the
reaction?
(1) CH3OH(3)C3H7OH
(2)C2H5OH(4)C4H9OH
3.
11. The hydrolysis of fat by a base is called
(1) saponification (3) polymerization
(2) esteriflcation (4) neutralization
12. Which is the product of the reaction between ethene and chlorine?
(1) H———Cl (3)
H H H H
H
(2) H—I—-Cl
H
H
(4) cl—c—cl
13. Which equation represents an esterification reaction?
(1)C6H12 — 2C2H50H + CO2
(2)C ÷H2—’C
(3)C3H8 + Cl 2 —C3H7CI + HCI
(4) HCOOH + CH3OH — HCOOCH + HOH
06
5H10 5H12
3
14. In a condensation polymerization, a product always formed is
(1) water (3) oxygen
(2) hydrogen (4) carbon dioxide
15. The organic reaction,
HCOOH +CH3CH2CH2CH2OH —, HCOOCH + HOH,
is an example of
(1) fermentation (3) polymerization
(2) esterification (4) saponification
H
2CH2CH2CH3
16. Which compound will undergo a substitution reaction with chlorine?
(1) CH4 (3)C3H6
(2)C2H4
(4)C4H8
17. The reaction represented by the equation nC2H4 —‘ (-C2H4-)n is
called
(1) saponification (3) esterification
(2) fermentation (4) polymerization
18. Which organic reaction involves the bonding of monomers by a
dehydration process?
(1) substitution (3) addition polymerization
(2) oxidation (4) condensation polymerization
19. The reaction CH3OH + HCOOH —. HCOOCH + H20 is an
example of
(1) hydrogenation (3) esterification
(2) polymerization (4) addition
3
20. The reactionC4H10 + 2—’C4H9Br + HBr is an example of
(1) substitution (3) fermentation
(2) addition (4) polymerization
© Evan P. Silberstein, 2003

16C0
________________________________
car: Form WS11.4.1A
Name
ORGANIC CHEMISTRY Date Period
Ua?.,i,i atic 1act3ir
Hydrocarbons participate in a variety of chemical reactions. Some are described below.
Combustion. Fossil fuels such as the gasoline used in automobiles or the propane used in gas barbecues are
hydrocarbons. When they burn, they release carbon dioxide and water. (CJH 8 + 502 —p 3C0 2 +4H20). Of course,
when there is insufficient oxygen, as in an automobile engine, the carbon does not oxidize completely, and carbon
monoxide and water forms. (2C 8H18 +
—
1702 + 18H 20). That is why automobile exhaust contains carbon
monoxide.
H H
Substitution. Saturated hydrocarbons have all their bonding
sites filled with hydrogen. The only way to attach any other
elements to the carbon chain of a saturated hydrocarbon is to I I
H
replace the hydrogen. The replacement of the hydrogen with
another element is called substitution. The diagram to the right
shows halogen substitution.
Addition. When there is a point of unsaturation, it is possible to
add elements to the hydrocarbon chain at that point without
removing any hydrogens. This is called addition. Unsaturated
bonds are more reactive than saturated bonds and alkynes are even
more reactive than alkenes, so additon of halogens occurs at room
temperature. Addition of hydrogen to an alkene or an alkyne (or
other carbon compounds with double or triple bonds) is called
hydrogenation. It is the processed used to make margarine from vegetable_oil.
Fermentation. Beverage alcohol is formed by yeast. It forms as a
result of the enzymatic breakdown of organic molecules during
anaerobic respiration. It is called fermentation.
Esterification. Esterification is the formation of esters (RCOOR).
Esters form from a reaction between an organic acid and an alcohol.
The alcohol and acid join by dehydration synthesis. The reaction looks
similar to an acid base neutralization. Esters are responsible for fniit
flavorings and aromas of flowers.
They are synthesized as artificial
flavors. Lipids (fats and oils) are
formed by esterification of glycerol
(1,2,3-propanetriol) by fatty acids
(long chain organic acids)
H—C— OH H —C—(CH,)a---—CH
Saponification. Saponification is the
H—C— OH H —C—(CH 2)——cH
hydrolysis of fats by bases. When
sodium hydroxide reacts with a fat it
produces organic salts called soaps
plus glycerol as a byproduct. The
reaction looks much like the reverse
of the formation of the fat, except
that the fatty acid becomes a sodium
H—C— OH
H
H —C—(CH,)——CH
salt [NaCH3(CH 2)C00].
H
ethane + bromine —1-bromoethane + hydrogen bromide
ethene + bromine —* 1,2 -dibromoethane
glucose
r H 0 H 0
2C2H50H + 2CO
ethanol + carbon dioxide
Alcohol + Acid — Ester + Water
2)——CH
3
3 H—c——--O—c—(CH
0 0
2)——CH
3 H—C——--O—C—(CH
0 0
2
3 +3H,O
2)----CH
3
3 H—,———O—C—(CH
1ycero1 + 3 Fatty acids Lipid + 3H20
Continue
Formation of fat by esterification
H

large molecules from repeating units of smaller
Polymerization. Polymerization is the formation of
ORGANIC CHEMISTRY Page 2
4
__________________________________________
_____________________
© Evan P. Silberstein, 2003
is this?
tetrafluoroethene. Then show the result of the reaction using structural formulas. What type ofpolymerization
6. Teflon, a common non-stick cooking surface, is a polymer of tetrafluoroethene. Draw a structural formula of
5. What is the process ofjoining many small molecules into larger molecules is called?
4. How is soap made?
will addition occur?
2. A hydrocarbon reacts with fluorine. Under which conditions will substitution occur, and under which conditions
1. What forms from the complete combustion of a hydrocarbon?
Answer the questions below based on the reading above and on your knowledge of chemistry.
many smaller, repeating units or monomers. Polymerization by condensation
—
Polymers can form by condensation
monomers by dehydration synthesis. Condensation
polymers must have at least two functional groups. The
process can be repeated to form long chain polymers.
Examples include silicones, polyesters, polyamides,
hydrocarbons. Examples
phenolic plastics, and nylons. Addition polymerization
involves opening up double and triple bonds ofunsaturated
include vinyl plastics -
polyethylene and polystyrene. Addition polymedzation
3. What is butylpentanoate? How does it form? ______________________________________________
c=cziHn
ones. A polymer is a large molecule formed from ________________________________________________
r[: Form WS 11 -
. 1A Understanding Organic Reactions
joining