Download ii Iii nil

_______________
Cr[:
___________
__________
____________
Name
Form WS11.3.2A
Har11$
Waiiit
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
with —OH at one end where a
H
hydrogen would have been. The
H—C—j--OH
—OH is called a functional group.
The rest of the molecule is called a
H
(R). The general formula
residue
H
H
OH, the
3
for alcohols is R—OH. CH
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
). As a result, it is called 14
(CH
H—C—C—C—--OH
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,
R—-OH
CHOH, formed from ethane,
3
CH
1-ethanol.
called
is
1-propanol.
is
H
H
3
CH
C
O
2
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.
I
I
I
Period
Date
ORGANIC CHEMISTRY
I
ii
Iii
H—C—C—C—H
I ,2,2-trifluoropropane
Table R
Organic Functional Groups
CIas of
Compound
Group
General
Formula
Example
—
R—X
(X represents
CHCICII
CH
3
(hakicarbon)
Cl (chioro-)
Br (bromo-)
-I (iodo-)
—
any halogen)
2-eblorepropane
alcohol
—OH
R011
ether
—0—
R—O—R’
0
0
—F(fluoro-)
halide
aldehyde
It
II
—C—H
R—C—H
ketone
0
II
—C—
0
II
R—C—R’
organic acid
0
It
—C—OH
0
II
fl—C—OH
ester
0
II
—c—o—
0
II
R—c—o—ir
ir
amine
amide
H
H,,UI
2
C
3
CH
O
1-propanol
H
OCI1
3
CH
C
2
methyl ethyl ether
0
II
—H
H
2
C
3
CH
C
propanal
0
H
CCHCH
CH
C
2
3
2-pentanone
0
II
—OH
CH.CH
C
2
propanoic acid
0
II
CNCHCOCH
methyl propanoate
HaNH
YJ
C
3
CH
C
2
N—
B—N—fl”
1-propanamine
0
It I
—C—NH
OR’
II I
fl—C—NH
0
It
CHaCNH
3
CH
2
popanamide
—
nil
H—C—C—C—C—H
Funcdonal
2-butanone
Name the following compounds using the rules for naming hydrocarbons and by referring to the reading and Table
R above.
CH,CHOHCH
CH
1. 3
2.
H——!!—J—H
H
H
Continue ir
__________
__________
________________
___________
_______________
______________
__________
_____________
___________
Naming Substituted Hydrocarbons
Form WS 11 3 2A
eitrf:
.
.
Page 2
ORGANIC CHEMISTRY
3.
H___J—!!—OH
H
H
CH
3
CH
O
C
4. 2
5. CHOCH
6.
H_L_i4__O—_J,_H
H
H
H
0
7
I
HCH
H
2
C
3
CH
C
H
HOHCH
8. 2
3
CH
C
C
HO
CH
C
9. 3
H
OOCH
H,CH
10. 2
3
CH
C
C
C
11.
H—i—J——OH
H
H
12. CC1
4
13. CF,CH,
0
14.
3
HC—O—CH
H
CH
CH
O
C
2
15. 3
H
H
H,CH
16. O
3
CH
C
C
2
H
CH
C
2
17. CH
CH,CHOH 3
3
H
HO
H,CH
3
CH
C
C
2
18. C
H
19. 2
CH,CHBrCH
3
CH
C
HNH
CH,CFI
3
CH
C
20. 2
© Evan P. Silberstein, 2003
__
ebrf:
Form Lsll.4A
Name
ORGANIC CHEMISTRY
5:rajjc
Date
Period
aci@i
to describe common reactions of organic compounds
Some reactions of hydrocarbons
* Combustion burning
with sufficient oxygen —‘ CO
2 and water
* example: C
8 + 502
H
2
3CC, + 4H
0
2
* with insufficient oxygen —‘ CO and water
* example: 2C
H, + 702 —‘ 6CC + 8H
3
0
2
* Substitution replacement of hydrogen in saturated
hydrocarbons
* example: halogen substitution
*
-
I
Ill
II
2
Br
+
H—C—C—H
-
““
-
-
H—C——C—H
Fermentation enzymatic breakdown of organic molecules
during anaerobic respiration
12
H
C
6
0
0H + 2C0
5
H
2
2
> 2C
glucose — ethanol + carbon dioxide
* Esterification formation of esters
* General formula: RCOOR
* Formation: ROH + RCOOH - RCOOR + H
O
2
* importance:
* fruit flavorings and aromas
* lipids are formed by esterification of glycerol by
fatty acids
* Saponification hydrolysis of fats by bases
* produces organic salts called soaps
* forms glycerol as a byproduct
* Polymerization formation of large molecules from
repeating units of smaller ones
* Polymer large molecule formed from many smaller,
repeating units or monomers
* Condensation - joining monomers by dehydration
synthesis
+
HBr
-
H
eth
ane + bromine
*
H
—,
H
monobromoethane
+
H
hydrogen bromide
-
Addition
* Definition = Adding two or more atoms to carbon at a
point of unsaturation
* Characteristics
* take place more easily than substitutions
* unsaturated bonds are more reactive than saturated
bonds and alkynes are more reactive than alkenes
* results in the formation of a single product
* Examples
* halogenation occurs at room temperature
H
H
HH
-
H
\
/
CC
/
\
+
H
2
Br
II
—
H-C-C-H
BrBr
* Hydrogenation
* Definition addition of hydrogen to an alkene or an
alkyne (or other carbon compounds with double or
triple bonds)
-
-
H
H
II
II
OH—C—C—OH
H
H
II
1
j
monomer
H
II
H
H
II
OH—C—C—OH —- OH—C—C—O—C—C—OH
)i
monomer
11
dimer
*
condensation polymers must have at least two
functional groups
* the process can be repeated to form long chain
polymers
* examples: silicones, polyesters, polyamides,
phenolic plastics, and nylons
* Addition polymerization involves opening up double
and triple bonds of unsaturated hydrocarbons
* examples: vinyl plastics - polyethylene, polystyrene
-
n
(
H\_/H
HH)
ethylene monomer
I
I
(--)
polyethylene
n
zrf:
ORGANIC REACTIONS
Form Nll.4A
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 between CH
COOH
3
and CH
OH is
3
(1)HOH
(3)HCOOH
(2) 4
S0
2
H
(4) O
2
C
3
CH
H
2. A fermentation reaction and a sponification reaction are similar in
that they both can produce
(3) an acid
(1) an ester
(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
6
H
3
(3)C
10
H
5
(1)C
(2) C
4
H
2
(4) C
8
H
4
4. The product of a reaction between a hydrocarbon and chlorine
was 1 ,2-dichloropropane. The hydrocarbon must have been
10
H
5
(1)C
6
H
3
(3)C
(2) C
(4) C
8
H
4
4
H
2
5. The reaction C
6
H
3
(1) substitution
(2) addition
+
6. The reaction C
4
H
2
(1) addition
(2) substitution
+
2—C
H
8 is an example of
H
3
(3) polymerization
(4) esterification
2
H
—‘
C is an example of
6
H
2
(3) saponification
(4) esterification
7. A reaction between an acid and an alcohol produces an ester and
(1) carbon dioxide
(3) glycerol
(2) water
(4) ethanol
12 will produce carbon dioxide and
H
C
6
8. The fermentation of 0
(1) a polymer
(3) an ester
(2) a soap
(4) an alcohol
9. The reaction: C
8
H
4
(1) substitution
(2) addition
+
2—C
Cl
2
C
8
H
4
I is an example of
(3) polymerization
(4) fermentation
12. Which is the product of the reaction between ethene and chlorine?
(3)
(1) H———Cl
H
H
H
H
(2)
H
H
(4)
H—I—-Cl
cl—c—cl
H
H
13. Which equation represents an esterification reaction?
0H + CO
5
H
2
2
(1) 0
12 — 2C
H
C
6
(2)C
—
2
÷H
1
H
5
’C
0
2
CI + HCI
7
H
3
(3) C
8 + Cl
H
3
2—C
OH — HCOOCH
3
3 + HOH
(4) HCOOH + CH
14. In a condensation polymerization, a product always formed is
(3) oxygen
(1) water
(4) carbon dioxide
(2) hydrogen
15. The organic reaction,
HCOOH + 2
3
CH
C
O
H
H —, 3
HCOOCH
C
2
H + HOH,
is an example of
(1) fermentation
(3) polymerization
(2) esterification
(4) saponification
16. Which compound will undergo a substitution reaction with chlorine?
(1) CH
4
(3) C
6
H
3
(4) C
8
H
4
(2) C
4
H
2
4
H
2
17. The reaction represented by the equation nC
called
(1) saponification
(3) esterification
(4) polymerization
(2) fermentation
—‘
(-C2H4-)n is
18. Which organic reaction involves the bonding of monomers by a
dehydration process?
(1) substitution
(3) addition polymerization
(2) oxidation
(4) condensation polymerization
10. A reaction between CH
COOH and an alcohol produced water
3
and an ester 3
COOCH Which alcohol was used in the
CH
.
reaction?
(1) CH
OH
3
(3) C
OH
7
H
3
(2) C
OH
5
H
2
(4) C
OH
9
H
4
19. The reaction CH
OH
3
example of
(1) hydrogenation
(2) polymerization
11. The hydrolysis of fat by a base is called
(1) saponification
(3) polymerization
(2) esteriflcation
(4) neutralization
20. The reaction C
10
H
4
(1) substitution
(2) addition
© Evan P. Silberstein, 2003
+
+
HCOOH
—.
3+H
HCOOCH
0 is an
2
(3) esterification
(4) addition
Br
—
2
’C
Br + HBr is an example of
9
H
4
(3) fermentation
(4) polymerization
________________________________
_______________________________
____________________________
_______
car:
Name
Form WS11.4.1A
Date
ORGANIC CHEMISTRY
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
0). Of course,
2
8 + 502 —p 3C0
2 + 4H
hydrocarbons. When they burn, they release carbon dioxide and water. (CJH
when there is insufficient oxygen, as in an automobile engine, the carbon does not oxidize completely, and carbon
0). That is why automobile exhaust contains carbon
2
16C0 + 18H
18 + 1702
H
8
monoxide and water forms. (2C
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 HI
H
replace the hydrogen. The replacement of the hydrogen with
ethane + bromine —1-bromoethane + hydrogen bromide
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
ethene + bromine —* 1,2 -dibromoethane
temperature. Addition of hydrogen to an alkene or an alkyne (or
bonds)
is
called
double
or
triple
carbon
compounds
with
other
hydrogenation. It is the processed used to make margarine from vegetable_oil.
Fermentation. Beverage alcohol is formed by yeast. It forms as a
0H + 2CO
5
H
2
2C
2
result of the enzymatic breakdown of organic molecules during
anaerobic respiration. It is called fermentation.
glucose ethanol + carbon dioxide
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
Alcohol + Acid — Ester + Water
flavorings and aromas of flowers.
H
0
0
They are synthesized as artificial r H
flavors. Lipids (fats and oils) are H—C— OH H
)——CH
2
H—c——--O—c—(CH
3
3
—C—(CH,)a---—CH
formed by esterification of glycerol
(1,2,3-propanetriol) by fatty acids
0
0
(long chain organic acids)
)——CH +3H,O
2
H—C——--O—C—(CH
3
)——cH
2
—C—(CH
Saponification. Saponification is the H—C— OH H 3
hydrolysis of fats by bases. When
0
0
sodium hydroxide reacts with a fat it
)----CH
2
H—,———O—C—(CH
3
3
produces organic salts called soaps H—C— OH H —C—(CH,)——CH
plus glycerol as a byproduct. The
H
H
reaction looks much like the reverse
of the formation of the fat, except 1ycero1 + 3 Fatty acids
+
0
2
3H
Lipid
that the fatty acid becomes a sodium
Formation of fat by esterification
(C00].
3
CH
)
CH
salt [Na 2
—
Continue
_____________________
___________
___________
___________
___________
___________
___________
___________
___________
___________
___________
___________
_________
___
____
Form WS 11
r[:
-
Understanding Organic Reactions
4 1A
.
ORGANIC CHEMISTRY
Page 2
Polymerization. Polymerization is the formation of
large molecules from repeating units of smaller
ones.
A
polymer
is
a
large
molecule
formed
from
many smaller, repeating units or monomers.
Polymers can form by condensation joining
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,
phenolic plastics, and nylons. Addition polymerization
involves opening up double and triple bonds of unsaturated
Polymerization by condensation
—
hydrocarbon
s.
Examples
include
vinyl
plastics
c=cziHn
-
polyethylene and polystyrene.
Addition polymedzation
Answer the questions below based on the reading above and on your knowledge of chemistry.
1. What forms from the complete combustion of a hydrocarbon?
2. A hydrocarbon reacts with fluorine. Under which conditions will substitution occur, and under which conditions
will addition occur?
3.
What
is
butylpentano
ate?
How
does
it
form?
4. How is soap made?
5. What is the process ofjoining many small molecules into larger molecules is called?
6. Teflon, a common non-stick cooking surface, is a polymer of tetrafluoroethene. Draw a structural formula of
tetrafluoroethene. Then show the result of the reaction using structural formulas. What type of polymerization
is this?
© Evan P. Silberstein, 2003