Download H - Sydenham High School

H H H H H H H H
| | | | | | | |
H-C-C-C-C-C-C-C-C-H
| | |
| | | |
H H H
H H H H
H H H
| | |
H-C-C-C-C-H
|
| |
H
H H
H-C-H
|
H-C-H
|
H
Here’s a structural
diagram of a typical
hydrocarbon
It has 14 C’s and 30
H’s so the formula is
C14H30
since each C is
surrounded by 4 bonds
typically, for ease of
drawing, the H’s are
left out to form a
carbon skeleton
diagram
To name the
parent chain
prefixes at the
beginning of the
C-C-C-C-C-C-C-C
word are used.
|
These prefixes are
C - C- C - C
|
This parent chain has 9 determined by the
C
| C so it starts with non. number of C
C If there are no double atoms in the
bonds it ends with ane parent chain.
Nonane is the name of the parent chain
Find the longest continuous
carbon chain. This structure
is called the parent chain.
Find the longest continuous
carbon chain. This structure
is called the parent chain.
If the carbon chain is
1 C starts with meth
2 C starts with eth
3 C starts with prop
C-C-C-C-C-C-C-C
4 C starts with but
|
5 C starts with pent
C - C- C - C
6 C starts with hex
|
This parent chain has 9 7 C starts with hept
C
| C so it starts with non. 8 C starts with oct
C If there are no double 9 C starts with non
bonds it ends with ane 10 C starts with dec
Nonane is the name of the parent chain
5
6
7
8
9
C-C-C-C-C-C-C-C
5
4
3
2
1
|
Using the red
C
CC
C
4
numbers the 1st
Next you must number 6 3 7
|
side chain is
the parent chain
Chains can be numbered 2 C 8
encountered at
from either direction so
the 5th C
|
the rule to follow states:
Using the blue
9
C
Number the chain so the 1
lowest possible number
is used when the 1st side
chain is encountered
numbers the 1st
side chain is
encountered at the
3rd C
5
6
7
8
9
C-C-C-C-C-C-C-C
|
3 C side
chain is
4C - C- C - C
3
called
|
2
C
side
propyl
2 C
chain is
Next, identify the
|
called
side chains and
1 C
ethyl
where they are
attached
Notice all side chains end in
yl
5
6
7
8
9
Now lets
consider the
names which
have been
determined
C-C-C-C-C-C-C-C
|
4C - C- C - C Parent chain is nonane
3
|
side chains are
3-ethyl and
2 C
5-propyl
the complete name is
|
1 C
3-ethyl-5-propylnonane
Side chains appear 1st and are always alphabetized, (ethyl
before propyl), parent chain appears last
Now draw the skeleton structure for 5-butyl6-ethyl-2-methyl decane
1st identify the parent chain
5-butyl-6-ethyl-2-methyldecane
(decane means 10 C’s with no double bonds
C-C-C-C-C-C-C-C-C-C
Side chains are:
|
| |
2-methyl
C
C C
(1 C attached to the 2nd C)
| |
C C
5-butyl
|
4 C’s attached to the 5th C
C
6-ethyl
|
2C’s attached to the 6th C
C
Now draw the skeleton structure for 3,3diethyl-2,5,6-trimethylheptane
1st identify the parent chain
3,3-diethyl -2,5,6-trimethylheptane (heptane
means 7C’s with no double bonds
C
Side chains are:
|
3,3-diethyl
C
|
(2C attached to each side
C-C-C-C-C-C-C
of the 3rd C)
| |
| |
C C
C C
2,5,6-trimethyl
|
1C’s attached to the 2nd, 5th and 6th
C
C
Name the following:
C
C-C C
|
| |
C-C-C-C-C-C-C-C
| | |
|
C C C
C
octane
Parent Chain is
2,2,3,4,7,7 hexamethyl
Final Answer is 6 - ethyl
6 - ethyl - 2,2,3,4,7,7 - hexamethyloctane
Side Chains are
Naming Cyclic Hydrocarbons with Side Chains
What is this structure called?
Number the carbons in the ring using the
lowest possible numbers.
CH2
CH3
5
H2C 4
1 CH2
CH3
3
CH2
2
CH2
CH3
1,2,4-trimethyl cyclopentane
Draw 2,3-diethyl-1-methylcyclohexane
CH3
CH2 HC
H2C
CH
CH2
CH3
CH2 HC
CH2
CH3
Aromatics with Side-Chains
CH2CH2CH3
Name?
1,3-dipropylbenzene
CH2CH2CH3
Sometimes compounds are more easily named
when the benzene ring is considered to be a
side chain.
CH
3
CH2
H3C
CH3
HC
CH
CH3
C
CH3
C
CH
CH
HC
CH
CH
Name?
2,2,3-trimethyl-4-phenylhexane
Draw 2,3-dimethyl-2,3-diphenylpentane
C
CH
CH
CH
HC
CH
C
C
C
C
C
CH3
C
H3C
H3C
CH2
C
CH3
C
C
CH
CH
HC
CH
CH
C
Alkyl Halides-Hydrocarbons containing
F, Cl, Br, I
When a halogen is introduced into a
hydrocarbon molecule naming proceeds as if
the halogen were simply a branch.
CH3CH2CHCH2CH3
|
Cl
is named
3-chloropentane
so
CH3CH2CH2CH2CH2CH2Br
is named
1-bromohexane
Draw the complete structural diagram for
4-bromo-2,5-dimethylheptane
HH HH H HH
| |
| | |
| |
H-C-C -- C-C - C -- C-C-H
| |
| | |
| |
H CH3 H Br CH3 H H
(CH3)2CHCH2CHBrCH(CH3)2
named
H
H H
H H HC H
HC C
C C
C H
H H C H H Br H C H
H
H
H
H H
H H HC H
HC C
C C
C H
H H C H H Br H C H
H
H
The parent chain is
Hexane
the rest of it is
3 - bromo
2,5 - dimethyl, so the complete name is
3-bromo-2,5-dimethylhexane
If double bonds are present, the hydrocarbon is
still named as if the halogen were absent.
F-CH=CH-CH2-CH3 is named
1-fluoro-1-butene
CH3-CH=CH-CH2I is
1-iodo-2-butene
CH2-CH=CH-CH2
|
|
Br
Br
is named
1,4-dibromo-2-butene
The condensed structural diagram for
1-chloro-6-iodo-2,4-hexadiene is
CH2-CH=CH-CH=CH-CH2
|
|
I
Cl
Cis and Trans Isomers
Molecules with double and triple bonds cannot
rotate in opposite directions on each side of the
double bond so when side chains, like Cl atoms
for example, are attached on each side of the
double bond 2 different structures are possible.
Cl
Cl
CH
CH
cis-1,2-dichloroethene
Cl
CH
CH
Cl
trans-1,2-dichloroethene
Br
CH2
H3C
C
C
CH3
Br
Name
trans-2,3-dibromo-2-pentene
H2C
H
CH2
Cl
H2C
H
CH2
Cl
H2C
H
CH2
Cl
H2C
H
CH2
Cl
H2C
H
CH2
Cl
H2C
H
CH2
Cl
H2C
H
CH2
Cl
H3C
CH2Cl
H
H
C
H
C
H
H
Cl
H
H
C
H
C
H
H
Cl
H
H
C
H
C
H
H
Cl
H
H
C
H
C
H
H
Cl
H
H
C
H
C
H
H
Cl
H
H
C
H
C
H
H
Cl
H
H
C
H
H
C
H
Cl
H
H
H
C
C
H
Cl
H
Addition Reaction
Hydrohalogenation of an Alkene to an
alkyl halide
C2H4 + HCl
ethene
C2H5Cl
chloroethane
Addition Reaction
Hydrohalogenation of an Alkene to an
alkyl halide
C2H4 + HCl
ethene
C2H5Cl
chloroethane
Markovnikov’s Rule
When non-identical atoms are added 2
products are theoretically possible.
Experiments show only 1 main product is
formed. The H atom will bond to the C atom
which already has more H’s attached.
2H’s H-CH=CH-CH3 + HBr
H2C – CH – CH3 or H2C – CH –CH3
H Br
Br H
2-bromopropane
1-bromopropane
Main product
The “rich” get “richer”
Predict the product for the reaction below
H
Br
H
HH
H
C
C
C
H
H
C
H
H
H
Br
H
HH
H
C
C
C
H
H
C
H
H
H
H
HH
Br
H
C
C
C
H
H
C
H
H
H
Br
H
H
HH
C
C
C
H
H
C
H
H
H
H HH
H
Br
C
C
C
H
H
C
H
H
H
HH
H
H Br
C
H
C
C
H
C
H
H
H
HH
H
C
Br C
C
C
H
H
H
H
H
H
H Br
C
H
H
HH
C
C
H
C
H
H
H
H HH
H
Br
C
C
C
H
H
C
H
H
H
Br
H
H
HH
C
C
C
H
H
C
H
H
H
Br
H
H
HH
C
C
C
H
H
C
H
H
H
Br
H
HH
H
C
C
C
H
H
C
H
H
H
Br
H
HH
H
C
C
C
H
H
C
H
H
H
Br
H
HH
H
C
C
C
H
H
C
H
H
Br
H
H
HH
H
C
C
C
H
H
C
H
H
Br
H
H
HH
H
C
C
C
H
H
C
H
H
Br
H
H
HH
H
C
C
C
H
H
C
H
H
Br
H
H
HH
H
C
C
C
H
H
C
H
H
Br
H
H
HH
H
C
C
C
H
H
C
H
H
Br
H
H
H
HH
C
C
C
H
H
C
H
H
The H atom will bond to the C atom with the
most H atoms already attached.
H
HH
Br
H H
C
H
C
C
H
C
H
H
H
H
H
H
H
C
C
C
H
Br
2-bromobutane
H
C
H
H
Draw structural diagrams showing the reaction
of HF and 1-pentene
H
H
HF +
H
C
C
H
C
H
C
C
H
H
H
H
H
H
H
C
H
C
H
H
F
H
C
H
C
C
H
H
2-fluoropentane
H
H
H2C
Cl
CH2
Cl
H2C
Cl
CH2
Cl
H2C
Cl
CH2
Cl
H2C
Cl
CH2
Cl
H2C
Cl
CH2
Cl
H2C
Cl
CH2
Cl
H2C
Cl
CH2
Cl
H2C
Cl
CH2
Cl
ClH2 C
CH2Cl
H
H
C
H
C
H
Cl
Cl
H
H
C
H
C
H
Cl
Cl
H
H
C
H
C
H
Cl
Cl
H
H
C
H
C
H
Cl
Cl
H
H
C
C
H
Cl
Cl
H
H
H
C
H
Cl
C
Cl
H
H
H
H
C
Cl
C
Cl
H
H
H
H
C
C
Cl Cl
H
Addition Reaction
Halogenation of an Alkene to an
alkyl halide
C2H4 + Cl2
ethene
C2H4Cl2
1,2-dichloro
ethane
H
H
H C
H
Cl
CH
H
Cl
H
H
H C
H
Cl
CH
H
Cl
H
H
H C
H
Cl
CH
H
Cl
H
H
H C
H
Cl
CH
H
Cl
H
H
H C
H
Cl
CH
H
Cl
H
H
H C
CH
H
Cl
H
Cl
H
H
H C
CH
H
Cl
Cl
Cl
H
H
H C
CH
H
Cl
Cl
Cl
H
H
H C
CH
H
Cl
Cl
Cl
H
H
H C
Cl
CH
H
Cl
Cl
H
H
H C
Cl
CH
H
Cl
Cl
H
H
H C
Cl
CH
Cl
H
Cl
H
H
CH
Cl
H C
Cl
H
Cl
Substitution Reaction
Changing an Alkane to an
alkyl halide
C2H6 + 2Cl2
ethane
C2H4Cl2 +2HCl
1,2 dichloro
ethane
Halogens have large electronegativities so their
presence on a hydrocarbon chain creates a polar region
which is localized. If they are present in a balanced
symmetrical pattern, the polarity is nulified and the
molecule is non-polar. (C2Cl6 for example).
Alkyl halides have stronger intermolecular forces than
their corresponding hydrocarbons due to this polarity,
so they have higher MP and BP and are more soluble
in polar solvents than hydrocarbons. The more
halogenated the hydrocarbon, the greater the polarity
and the higher the MP and BP.
are characterized by the presence of an OH
group (hydroxyl). The alcohol whose
parent hydrocarbon is propane can have
two possible structures which are derived
by replacing an H atom with an OH group.
H OH
H OH
H
OH
| | |
H - C - C - C - OH
H
OH
H
| | |
OH
OH
OH
H OH
H H
Notice the OH group is
either attached to the 1st
or the 2nd C so the 2
possible names are
1-propanol
2-propanol
Alcohols end in ______ol.
Name this structure
CH3(CH2)7OH
1-octanol
Name this structure
CH3 CH2 CH2 CH CH2 CH2CH2CH3
|
CH2 CH2OH
When a functional group like OH is present find the
longest carbon chain which contains the functional
group. The OH group is on the 1st carbon.
3-propyl-1-heptanol.
Name this structure CH3 CH2 CHCH3
|
OH
2-butanol not 3 butanol is the correct name
CH3 CH2 CH2 CH(OH) CH2 CH3
is named
3-hexanol
Once the numbering system is determined by
the location of the OH group, other branches,
alkyl or halogen are named in the usual way
CH3
|
CH3 -CH2 - C - OH is named
|
2-methyl-2-butanol
CH3
CH3
CH2 CH3
|
|
CH3 C CH2 CH2 CCH3
|
|
CH3
CH CH3
|
OH
Find the longest C
chain which contains
the OH group
is named
3-ethyl-3,6,6-trimethyl-2-heptanol
If a carbon chain has more than one OH
group attached it is called a polyhydroxy
compound.
Draw a structural diagram of 1,2-ethanediol.
CH2 OH
|
CH2 OH
the common name for this is ethylene glycol
the principal component of antifreeze.
CH2 OH
|
CH3CH2 - C-OH
|
CH2 OH
Its name is
2-ethyl-1,2,3-propantriol
The insect repellent “6-12” (2-ethyl1,3-hexanediol) has the structural
formula:
H H H H H H
| |
| | | |
H - C - C --- C - C - C - C - H
| |
| | | |
OH CH2 OH H H H
|
CH3
What is the name of the structure below:
OH
|
CH
/ \
CH2 CH2
|
|
CH CH
/ \ / \
OH CH2 OH
1,3,5-cyclohexanetriol
CH3CH=CH-CH2-OH is named
2-buten-1-ol
CH2=CH-CH2OH is named
2-propen-1-ol
the OH group takes precedence in numbering
3-buten-2-ol has the formula:
H H H
H
| | |
/
H-C-C-C=C
| |
\
H OH
H
If there is a choice of chains, the most
unsaturated is chosen as long as it still contains
the OH group
Example - What is the name of:
CH3 - CH = C - CH2 - OH
|
CH2CH2CH3
the parent chain is
The complete name is
2 - propyl - 2 - buten -1- ol
Remembering the compounds with triple bonds
are called alkynes, the structural diagram for
2-propyn-1-ol is
H
|
H-C-C C-H
|
OH
CH3-CH2-C-CH2-CH-CH3
|
|
CH3 CH2OH
2,4 - dimethyl-1-hexanol
is
The formula for
2,2,5-trimethyl-3-hexene-1,5-diol is
CH3
OH
|
|
CH2-C-CH=CH-C-CH3
|
|
|
OH CH3
CH3
H2C
H
CH2
H
O
H2C
H
CH2
H
O
H2C
H
CH2
H
O
H2C
H
CH2
H
O
H2C
H
CH2
H
O
H2C
H
CH2
H
O
H2C
H
CH2
H
O
ethanol
H
O
H
H
C
H
H
C
H
H
H
C
C
H
H
O
H
H
H
H
C
C
H
H
O
H
H
H
H
C
C
H
O
H
H
H
H
H
C
C
H
O
H
H
H
H
H
C
H
H
C
H
O
H
H
H
H
C
C
H
O
H
H
Addition Reaction
Hydration of an Alkene to an
alcohol
C2H4 + H2O
ethene
C2H5OH
ethanol
The presence of the OH group makes them polar
so they are soluble in water and other polar
solvents and can form H bonds which is a
stronger intermolecular force that dipole-dipole
attractions found between polar molecules.
As the non-polar hydrocarbon chain grows in
the higher molecular weight alcohols the
polarity decreases so the solubility diminishes
but they can be used to dissolve both non-polar
and polar substances.
Larger molecular weight alcohols also have
stronger intermolecular forces so BP increases.
Oxygen atoms can bond in the middle of a
chain of carbon atoms. When this happens
the compounds formed are called ethers.
Example
CH3-CH2-O-CH2-CH2-CH2-CH3
The longest chain is used as the parent chain.
This 4 carbon chain is called butane
the side chain is 2 C’s + the O
The side chain is called ethoxy
ethoxybutane
Sketch 1,2-dimethoxycyclopentane
Parent chain is cyclopentane
side chains are methoxy attached to
consecutive carbons in the 5 Carbon ring
CH2
/
\
CH2 CH-O-CH3
|
|
CH2---CH-O-CH3
Name this structure
CH2=CH-CH-CH2-CH-CH2-CH3
|
|
CH3-CH2-O
O-CH2-CH2-CH3
parent chain is
1-heptene
side chains are
3-ethoxy and 5-propoxy
complete name is
3-ethoxy-5-propoxy-1-heptene
H
H
H
C
C
O
H
H
H
C
H
H
2-propanol
H
H
H
C
H
O
C
H
H
C
H
H
H
H
H
C
C
O
H
H
H
H
C
O
C
H
H
H
H
H
C
H
2-propanol
H
C
H
H
H
H
H
C
C
O
H
H
H
C
H
O
C
H
H
H
H
H
C
H
H
C
H
2-propanol
H
H
H
H
H
H
C
H
C
C
O
H
C
H
H HH
O
C
H
H
H
C
H
2-propanol
H
H
H
H
C
C
H H
O
C
H
C
H
H
H
C
H
H H
C
H
O
H
H
H
H
H
H
H
C
H
C
H
CH
H
H
C
H
O
C
H
C
O
H
H
H
2-methylethoxypropane
H
H
Dehydration of
Alcohols to Ethers
2C3H7OH
2-propanol
H2SO4
C6H14O +H2O
2- methylethoxy
propane
The difference in En of C and O, and the V
shape of the C – O – C bond make ethers
slightly polar. Their MP and BP lie in between
those of corresponding alcohols and
hydrocarbons.
They mix readily with both polar and nonpolar
substances so make excellent solvents for
organic reactions. The C-O bond is quite stable
making ethers generally unreactive, another
property of a good solvent.
Both these families have C = O groups
replacing a H atom on the carbon chains.
Aldehydes have this C = O group at the
end of a chain, Ketones have the C = O
group in the middle portion of the chain.
Here are some examples of aldehydes
and ketones. Decide which is which.
A. CH3HC=O
aldehyde
B. CH3CH2C = O
ketone |
CH3
C. (CH3)2CHCCH(CH3)2
||
ketone
O
E.
CH3COCH3
ketone
D. HCHO
aldehyde
F.
HCOC2H5
aldehyde
Aldehydes end in _______________al
Ketones end in _______________one
ethanal is
CH3-C=O
|
H
propanone is
CH3-C-CH3
||
O
Pentanone has 2 possible structures.
They are
CH3CCH2CH2CH3 2 - pentanone
||
O
and
CH3CH2CCH2CH3 3 - pentanone
||
O
Name this structure
CH3
|
O=CCHCH2CH3
|
CH3
the parent chain is
3-methyl-2-pentanone
2,3-hexanedione is
C-C-C-C-C-C
|| ||
O O
1,4-cyclohexanedione is
CH2
/ \
CH2 C=O
|
|
O=C
CH2
\ /
CH2
3-penten-2-one is
The functional group takes
precedence over the double
bond
C-C-C=C-C
||
O
3-hydroxypentanal is
C-C-C-C-C
||
|
O
OH
5-chloro-3-heptenal is
C-C-C=C-C-C-C
||
|
O
Cl
Name this
CH3C=O
|
CH2CH-CH3
|
I
4-iodo-2-pentanone
2,5-heptadien-4-one has the
structural formula
CH3CH=CH-C-CH=CHCH3
||
O
KMnO4 or Cr2O72- in H2SO4
O
1-propanol
H
H
O
H
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
O
H
H
O
H
1-propanol
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
O
H
H
O
H
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
O
H
H
O
H
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
O
H
H
O
H
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
OH
H
O
H
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
O H
H
O
H
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
O H
H
H
O
H
C C
C
H H
H H
KMnO4 or Cr2O72- in H2SO4
O H
H
dehydration reaction
H
O
H
C C
C
H H
H H
propanal
KMnO4 or Cr2O72- in H2SO4
O
2-propanol
H
H
H
C
C
H
H
C
OH
H
H
KMnO4 or Cr2O72- in H2SO4
O
2-propanol
H
H
H
C
C
H
H
OH C H
H
KMnO4 or Cr2O72- in H2SO4
O
H
2-propanol
H
H
C
C
H
H
C
OH
H
H
KMnO4 or Cr2O72- in H2SO4
O
H
2-propanol H
H
C
C
H
H
OH C H
H
KMnO4 or Cr2O72- in H2SO4
H
H
2-propanol
H
C
C
H
O
H
OH C H
H
KMnO4 or Cr2O72- in H2SO4
H
H
H
C
C
H
O
H
C
OH
H
H
KMnO4 or Cr2O72- in H2SO4
H
H
H
C
C
H
O
H
C
H
O
H
H
KMnO4 or Cr2O72- in H2SO4
H
O
H
H
H
C
C
H
O
H
C
H
H
KMnO4 or Cr2O72- in H2SO4
Notice when
the
OH
H
group is not
O
on the end a
H
ketone is
made
propanone
H
H
C
C
H
O
H
C
H
H
Oxidation of Alcohols
to Aldehydes or Ketones
1-propanol
C3H7OH + O
2-propanol
propanal
C3H6O + H2O
propanone
The C = O bond is polar so aldehydes and
ketones are soluble in water and their MP and
BP lie between corresponding hydrocarbons
and alcohols since the O – H bond is more
polar. They also can mix with non-polar
substances due to the presence of hydrocarbon
chains. The longer the chains the more nonpolar they are, the less soluble they are in polar
solvents and the more soluble they are in nonpolar solvents.
Again as their molecular weights increase so
do their MP and BP due to increased VdW forces.
Ethanoic Acid is
CH3C=O
|
OH
the name of this is
CH3CH2CH=CHCOOH
2-pentenoic acid
4-hydroxy-3-iodo-2-heptenoic acid is
C-C-C-C-C=C-C=O
| |
|
OH I
OH
Name this
CH3-CH-CH2-CH2-CH3
|
COOH
2-methylpentanoic acid
KMnO4 or Cr2O72- in H2SO4
H
O
O
H
C C
C
H H
H H
propanal
KMnO4 or Cr2O72- in H2SO4
H
O
O
H
C C
C
H H
H H
propanal
KMnO4 or Cr2O72- in H2SO4
H
O
O
H
C C
C
H H
H H
propanal
KMnO4 or Cr2O72- in H2SO4
H
O
O
H
C C
C
H H
H H
propanal
KMnO4 or Cr2O72- in H2SO4
H
O
O
H
C C
C
H H
H H
propanal
KMnO4 or Cr2O72- in H2SO4
H
O
H
C C
C
H H
O
H H
propanal
KMnO4 or Cr2O72- in H2SO4
`
H
O
C
H
C
C
O H H H H
propanal
KMnO4 or Cr2O72- in H2SO4
`
H
O
C
O
H
H
C
C
H
H H
propanal
KMnO4 or Cr2O72- in H2SO4
H
O
C
H
C
O H C
H
H
H
Propanoic
acid
`
Oxidation of Aldehydes
to Carboxylic Acids
C3H6O + O
propanal
C2H5COOH
propanoic acid
Organic acids are polar and form H bonds so
they are soluble in water. As molecular weights
increase, intermolecular forces increase so BP
and MP increase.
As the hydrocarbon chain grows, the polarity
decreases so the solubility in polar solvents
decrease.
H
H
C
H
C
O
H
O
H
H
H
H
H
C
C
C
O
H
H
H
H
H
C
H
C
O
H
O
H
H
H
H
H
C
C
C
O
H
H
H
H
H
C
H
C
O
H
O
H
H
H
H
H
C
C
C
O
H
H
H
H
H
C
H
C
O
H
O
H
H
H
H
H
C
C
C
O
H
H
H
H
H
C
H
C
O
H
H
O
H
H
H
H
H
C
C
C
O
H
H
H
H
C
H
C
O
H
H
O
H
H
H
H
H
C
C
C
O
H
H
H
H
C
H
C
O
H
H
O
H
H
H
H
H
C
C
C
O
H
H
H
H
C
H
H
C
H
O
H
H
H
C
O
C
H
C
O
H
H
H
H
H
H
C
C
O
H H
H
H
H
O
H
C
C
C
H
O
H
H
H
H
H
H
H
C
C
H
O
H
H
O
H
C
C
C
H
O
H
H
H
H
H
C
C
H
O
H
H
O
C
O
H
C
H
H
C
H
H
H
H
H
H
C
C
H
O
ethyl
propanoate
H
H
C
O
H
C
H
H
C
H
H
O
H
Making Esters from Alcohols and Acids
C2H5OH + C2H5COOH
C2H5COOC2H5 + H2O
C - C - C - C - OH
Alcohol is called
1-butanol
O=C-C-C-C-C
|
Acid is called
OH
Pentanoic acid
When they combine H2O is removed
(a dehydration synthesis)
O=C-C-C-C-C
|
OH
C - C - C - C - OH
C - C - C - C - OH
C - C - C - C - OH
O=C-C-C-C-C
|
O
|
C-C-C-C
O=C-C-C-C-C
|
O 1-butyl pentanoate
|
C-C-C-C
When naming esters you name the alcohol 1st (remove
the letters anol from the end and add the letters yl at
the end.
If the alcohol is 1-butanol then the name is 1-butyl.
The acid name is second. If the acid is pentanoic drop
the last 3 letters (oic) and add the letters oate.
In this instance it becomes pentanoate. The complete
name becomes
O=C-C-C-C
|
This ester’s
Ethyl
butanoate
name is
O
| Remember the double bonded
oxygen atom is always joined to
C - C the acid
Remember alcohol Ethanol becomes
1st
Acid 2nd
Butanoic becomes
ethyl
butanoate
What is this ester’s name?
O=C-C
|
2-pentylethanoate
O
|
C-C-C-C-C
Remember alcohol 2-pentanol becomes 2-pentyl
1st
Acid 2nd
ethanoic becomes
ethanoate
Draw the structural diagram for 2,3,3trichloro-2-hexylmethanoate
Remember alcohol
1st
Cl Cl
| |
C-C-C-C-C-C
| |
OH Cl
OH
|
O=C
Cl Cl
| |
C-C-C-C-C-C
| |
O Cl
|
O=C
Esters lack the OH group from the parent acid
and alcohol so they are less polar.
This means they have lower MP and BP than
their corresponding acids and alcohols are less
soluble in water and are not acidic.
Smaller molecular weight esters have relatively
weak intermolecular forces so they have strong
odours.
NH2 groups can be attached as side
chains to carbon parent chains. These
groups are called amines. Here is an
example.
1,2-diaminopropane is
CH2-CH-CH3
|
|
NH2 NH2
What is the name of this structure?
F-C=C-C-C-C-NH2
|
NH2
3,5-diamino-1-fluoro-1-pentene
notice the double bond takes
precedence over the side chains. When
a functional group is present like
alcohols (OH), aldehydes (C=O),
ketones, or acids, they take precedence
over the double or triple bonds.
The hydrogens on the amines can be
replaced by methyls (CH3), ethyls
(C2H5) , halides (F), etc.
CH3-CH-CH3
|
N
/ \
CH
H 3 CH2H5
When this happens the side
chain is called
N-ethyl-N-methyl-2-amino
propane
H
H
H
H
C
C
H
Cl
H
H
N
H
H
H
H
H
C
C
H
Cl
H
H
N
H
H
H
H
H
C
C
H
Cl
H
H
N
H
H
H
H
H
C
C
H
Cl
H
H
N
H
H
H
H
H
C
C
H
Cl
H
H
N
H
H
H
H
H
C
C
H
Cl
H
H
N
H
H
H
H
H
C
C
H
Cl
H
H
N
H
H
H
H
C
C
H
Cl
H
H
H
N
H
H
H
H
C
C
H
H
H
Cl
N
H
H
H
H
H
C
C
H
H
H
Cl
N
H
H
H
H
H
C
C
H
H
H
Cl
N
H
aminoethane
H
Making Amines
From Alkyl Halides
CH3CH2Cl + NH3
C2H5NH2 + HCl
Amines are named as side chains.
Name this compound
NH2
CH
C
H3C
H2N
Draw 2,2 diamino-6-methyl3,5-octadiene
CH
CH3
Parent chain is 2-pentene
4,4-diamino-2-pentene
NH2
H3C
H2N
C
CH
C
CH
CH3
CH2
CH
H3C
N – H and C – H bonds are both polar and
N – H bonds exhibit H bonding properties so
amines are quite soluble in water.
Neither bond is as polar as O – H so they have
lower MP and BP than their corresponding
alcohols. As molecular weight increases so does
BP and MP unless no H bonding occurs. Match
these MP to the diagrams
8oC, -33oC, 6oC.
H
NH
H
H3C
H
NH
H3C
H3C
NH
Remember the carboxylic acids
Ethanoic Acid is If the OH group is
replaced by an
CH3C=O
amine the resulting
|
functional
group
is
NH
OH2
called an amide.
Ethanamide Amides are named
from the parent
3-ethyl-2-pentenamide is
CH3-CH2-CH=CH-C=O
|
|
C2H5
N
/ \
H H
If the H’s on the NH2 are replaced
by a methyl and an ethyl
CH3-CH2-CH=CH-C=O
|
|
C2 H5 N
/ \
H
H
CH
C
The name is
3
2 H5
N-ethyl-N-methyl-3-ethyl-2-pentenamide
Sketch the following
N-ethylbutanamide
CH3-CH2-CH2-C=O
|
N
/ \
C2H5 H
H
H
H
C
C
H
H
N
H
H
H
H
C
C
C
O
H
H
H
O
H
H
H
H
C
C
H
H
N
H
H
H
H
C
C
C
O
H
H
H
O
H
H
H
H
C
C
H
H
N
H
H
H
H
C
C
C
O
H
H
H
O
H
H
H
H
C
C
H
H
N
H
H
H
H
C
C
C
O
H
H
H
O
H
H
H
H
C
C
H
H
N
H
H
H
H
C
C
C
O
H
H
H
O
H
H
H
H
C
C
H
H
N
H
H
H
H
C
C
C
O
H
H
H
O
H
H
H
H
C
C
H
H
N
H
H
H
O
H
H
C
C
C
O
H
H
H
H
H
H
C
C
H
H
N
H
H
H
O
H
H
C
C
C
O
H
H
H
H
H
H
C
C
H
H
N
H
H
O
H
H
H
C
C
C
O
H
H
H
H
H
H
C
C
H
H
N
H
H
O
H
H
H
C
C
C
O
H
H
H
H
H
H
C
C
H
H
N
H
H
O
H
H
H
C
C
C
O
H
H
H
H
H
H
C
C
H
H
N
H
H
O
N-ethylpropanamide
H
H
H
C
C
C
O
H
H
H
Making Amides From Amines and Acids
C2H5NH2 + C2H5CO2H
C2H5CONHC2H5
+ H2O
Amides are generally insoluble in water due to
the relative cancellation of the 4 different polar
regions (the two N – H s, the C = O and the
C - N). The lower molecular weight amides are
slightly soluble due to the presence of H
bonding.
Amides which have alkyl groups attached to the
N atom have weaker intermolecular forces (due
to lack of H bonding) so have lower MP and BP.
The lone pair of electrons found on the N atom
makes it attractive to H atoms so amines are
weak bases.
NO2 groups can be attached as side chains
to carbon parent chains. These nitro groups
as named as side chains much like halogens
(Cl), ethers (OCH3) and hydroxys (OH).
Here is an example.
3-nitro-1-hexene has the structure
CH2=CH-CH-CH2-CH2-CH3
|
NO2
Sketch 1-methyl-2,3,4-trinitro-1,3,5cyclohexatriene (TNT)
NO2
C
NO2
NO2
C
C
C
C
C
CH3
This structure is also
called trinitrotoluene
(TNT). A benzene
H ring with a methyl
group is called
H toluene. Benzene is
also drawn like this
Br
and when functional groups are
attached at adjacent locations the
Cl
Br
F prefix ortho(o) is used. Here are
examples of o-dichlorobenzene
If functional groups are on
carbons separated by one
Cl
F
Cl
F
Br
empty carbon the prefix used
is meta (m) Here are examples
Cl
Br
F
of m -difluorobenzene.
If functional groups are on carbons separated by
two empty carbons the prefix used is para (p) Here
are examples of p -dibromobenzene.
20 different amino acids are used to assemble
protein. Like the name implies amino acids
have amino and carboxylic acid groups on
adjacent carbons.
Each of the 20
different amino acids
has a different R
group.
R OH
| |
H-C-C=O
|
NH2
If the R group is methyl the amino acid is
called alanine. Its structure is
CH3 OH
| |
H-C-C=O
|
NH2
If the rules presented
previously were used to
name alanine it would be
called
2 - aminopropanoic acid
If serine is named 2-amino-3hydroxypropanoic acid what is its structure?
2-amino-3-hydroxypropanoic acid
H OH
| |
OH-CH2-C-C=O
|
NH2
Most of the dry mass of living organisms is
composed of proteins. Proteins are
composed of long chains of the 20 different
amino acids linked end to end.
Here is an example of how amino acids are
chemically bonded. The product produced
from 2 amino acids is called a dipeptide.
Here is how dipeptides form.
When 2 different amino
acids combine the amino group
of one amino acid always reacts
with the carboxyl group of the
other amino acid.
Notice water is
eliminated so
this kind of
reaction is called
a dehydration
synthesis. The
product is called
a dipeptide.
H OH
| |
H-C-C=O
|
NH2
CH3 OH
| |
H-C-C=O
|
N
/ \
H H
H OH
| |
H-C-C=O
|
NH2
CH3 OH
| |
H-C-C=O
|
N
/ \
H H
CH3 OH
| |
H-C-C=O
|
N
H2O + \
H H
|
H-C-C=O
|
NH2
Remember a peptide linkage occurs
between the amino group of one
amino acid and the carboxyl group of
another. Water is always eliminated
in this dehydration synthesis.
Show how a peptide bond forms from
2 amino acids if one has an R group
which is a hydroxy and the other’s R
group is an ethyl.
OH OH
| |
H-C-C=O
|
C2H5 OH H-N-H
| |
H-C-C=O
|
H-N-H
OH OH
| |
H-C-C=O
|
N-H
C2H5
+ H20
|
H-C-C=O
|
H-N-H
To watch a movie showing polypeptide
formation click here
Making Aspartame - A dipeptide
HO
O
NH2
180x's
sweeter
than
sugar
Phenylalanine
Systematic name?
2-amino-3-phenyl-propanoic acid
Making Aspartame - A dipeptide
HO
OH
O
NH2
O
Aspartic acid
Systematic name?
Aminobutandioic acid
Making Aspartame
HO
O
N
H
H
HO
OH
O
NH2
O
Making Aspartame
HO
O
N
H
H
HO
OH
O
NH2
O
Making Aspartame
HO
O
N
H
H
HO
OH
O
NH2
O
Making Aspartame
HO
O
HN
OH
O
NH2
O
Methyl ester of a Dipeptide
H3C
methanol
OH
HO
O
HN
OH
O
NH2
O
Methyl ester of a Dipeptide
H3C
methanol
OH
HO
O
HN
OH
O
NH2
O
Methyl ester of a Dipeptide
H3C
methanol
OH
HO
O
HN
OH
O
NH2
O
Methyl ester of a Dipeptide
H3C
O
O
HN
OH
O
NH2
O
Methyl ester of a Dipeptide
10% of ingested aspartame is changed
into methanol which is poisonous
Doseage from 1 diet drink is minimal
Sucralose is probably better as an
artificial sweetner.
Show where this hydrolysis happens.
H3C
O
O
HN
OH
O
NH2
O
Methyl ester of a Dipeptide
H3C
O
H
O
H
O
HN
OH
O
NH2
O
Methyl ester of a Dipeptide
H3C
OH
HO
O
HN
O
Methanol is further oxidized into
methanal, then methanoic acid.
Draw these reactions.
Methanoic acid can be toxic at high
levels due to its inhibition of
cytochrome c oxidase the last
enzyme in the electron transport
chain in the mitochondria. It
OH the electrons to oxygen.
transfers
Complete
inhibition is fatal.
NH
O
2
sucralose
Sucrose -white sugar
Notice the
similarites
between
sucralose and
sucrose.
Compare to
aspartame
sucralose
H3C
Aspartame
O
O
HN
OH
O
Sucrose -white sugar
NH2
O
Making Acetylsalicylic Acid (ASA) Aspirin
HO
H3C
O
O
O
OH
+
HO
O
O
+
O
O
H 3C
CH3
OH
O
H3C
Salicylic acid
Acetic anhydride
Ethanoyl ethanoate
ASA
Ethanoic acid
Acetic acid
5% is vinegar
Let's focus on the acetic anhydride.
O
H3C
O
O
CH3
O
CH3
OH
H3C
HO
O
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
Let's focus on the acetic anhydride.
O
H3C
O
O
CH3
O
CH3
OH
H3C
HO
O
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
Let's focus on the acetic anhydride.
O
H3C
O
O
O
CH3
O
O
H3C
CH3
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
Let's focus on the acetic anhydride.
O
H3C
O
O
O
H3C
CH3
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
O
O
CH3
When an anhydride is placed in water it will undergo the reverse reaction
(hydrolysis). Water is added and it reforms the 2 original molecules, in
this case the ethanoic acid.
O
H3C
O
O
H
O
H
CH3
Let's focus on the acetic anhydride.
O
O
H3C
O
CH3
O
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
O
H3C
O
CH3
When an anhydride is placed in water it will undergo the reverse reaction
(hydrolysis). Water is added and it reforms the 2 original molecules, in
this case the ethanoic acid.
O
H3C
O
OH
HO
H
CH3
Let's focus on the acetic anhydride.
O
H3C
O
O
O
H3C
CH3
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
O
O
CH3
When an anhydride is placed in water it will undergo the reverse reaction
(hydrolysis). Water is added and it reforms the 2 original molecules, in
this case the ethanoic acid.
O
H3C
O
OH
OH
H
CH3
Let's focus on the acetic anhydride.
O
H3C
O
O
O
H3C
CH3
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
O
O
CH3
When an anhydride is placed in water it will undergo the reverse reaction
(hydrolysis). Water is added and it reforms the 2 original molecules, in
this case the ethanoic acid.
O
H3C
O
OH OH
H
CH3
Let's focus on the acetic anhydride.
O
H3C
O
O
O
H3C
CH3
All anhydrides are created by the
elimination of water. This
anhydride is formed by the
reaction of 2 acetic acid
molecules with the elimination of
water (dehydration)
O
O
CH3
When an anhydride is placed in water it will undergo the reverse reaction
(hydrolysis). Water is added and it reforms the 2 original molecules, in
this case the ethanoic acid.
O
H3C
O
OH HO
CH3
Now the ethanoic acid can undergo an
esterification with the alcohol group of the
salicylic acid to form the ASA
HO
O
CH3
OH HO
O
Now the ethanoic acid can undergo an
esterification with the alcohol group of the
salicylic acid to form the ASA
HO
O
CH3
OH HO
O
Now the ethanoic acid can undergo an
esterification with the alcohol group of the
salicylic acid to form the ASA
HO
O
CH3
OH HO
O
Now the ethanoic acid can undergo an
esterification with the alcohol group of the
salicylic acid to form the ASA
HO
O
CH3
O
O
ASA will sometimes smell like alcohol. This
happens when the ester is hydrolyzed by water
to reform the salicylic acid and ethanoic acid
HO
O
CH3
O
O
ASA will sometimes smell like alcohol. This
happens when the ester is hydrolyzed by water
to reform the salicylic acid and ethanoic acid
HO
O
CH3
O
O
H
O
H
ASA will sometimes smell like alcohol. This
happens when the ester is hydrolyzed by water
to reform the salicylic acid and ethanoic acid
HO
O
CH3
O
H
O O
H
ASA will sometimes smell like alcohol. This
happens when the ester is hydrolyzed by water
to reform the salicylic acid and ethanoic acid
HO
O
CH3
OH
HO
O
ASA will sometimes smell like alcohol. This
happens when the ester is hydrolyzed by water
to reform the salicylic acid and ethanoic acid
HO
O
HO
CH3
OH
O
Nylon is composed of gigantic molecules
made up of a repeating subunit called a
monomer. These extremely large molecules
made up of large numbers of monomers are
called polymers. Dupont, in Kingston,
makes a kind of nylon called nylon 6,6. It is
made from a 6 carbon dicarboxylic acid and
a 6 carbon diamino compound.
1,6-diaminohexane (hexamethylene
diamine) is one of these
compounds and hexandioic acid
(adipic acid) is the other. These
molecules are combined end to end
by releasing water in a dehydration
synthesis. Show how this is done.
O=C-(CH2)4-C=O
CH2-(CH2)4-CH2
|
|
|
|
OH
OH H-N-H
H-N-H
hexandioic acid 1,6-diaminohexane
O=C-(CH2)4-C-N-CH2-(CH2)4-CH2
|
|| |
|
OH
O H
H-N-H
This n means this basic monomer is repeated over and over
To watch a movie click here.
n
Polymers made by the removal of
water are called condensation
polymers.
Polyesters, like Dacron, are
examples of this type of polymer.
Esters are made by combining
alcohols and acids.
To watch a movie of polyester
formation click here
Dacron is made from 1,2-ethanediol
(ethylene glycol) and paradibenzoic acid (pphthalic acid). Show how this polymer is
made from these 2 monomers.
HO
O
O
C
C
O
HO
C
OH
HO
CH2
CH2
OH
HO
O
C
O
CH2 CH2 O
O
O
C
C
OH
O
O
CH
C
HO
O
CH2
CH2
OH
CH2 CH2 OH
Addition Polymerization
Alkene monomers can be combined by breaking
double bonds. For movie click here.
ethene
H
H
C
C
H
H
C
+
H
H
C
H
H
H
C
H
H
C
H
H
H
C
H
C
H
H
H
H
H
C
C
+
H
H
H
C
C
H H
H
polyethylene
Addition polymerization has 3 steps
Initiation - a peroxide becomes a free radical( a
compound with an unshared electron)
When the free radical collides with a monomer
it steals only 1e1- from the double bond leaving
behind another free radical.
This begins the 2nd stage called elongation.
The chain continues to grow until 2 free radicals
collide and form a stable polymer. This stage is
called the termination of the polymerization.
Show how addition polymers can be made
from Propene, chloroethene, and phenylethene
(styrene).
These polymers are called polypropylene,
polyvinyl chloride, and polystyrene.
propene
H
C
H
H
C
+H
C
C
H
H
H
H
H
H
H
H3C
polypropylene
C
C
H
H
H
CH2
CH2
CH2
H
C
H
HC
CH
H3C
+
C
C
H
H
CH3
CH3
H
H
C
C
CH3H
n
chloroethene
HC
CH2
HC
+
Cl
CH2
Cl
CH2
HC
+
Cl
CH2
CH
CH2
Cl
Polyvinyl chloride (PVC)
CH2
Cl
CH
Cl
CH3
H
H
C
C
H Cl
n
Phenylethene (styrene)
CH
CH2
CH
+
CH
CH2
+
|
| |
|
|
|
-C – C – C – C – C – C –
|
|
|
|
|
|
H H
C
H
polystyrene
CH2
C
n
Addition polymerization occurs in 3 stages:
Initiation, propagation and termination.
An initiating molecule like peroxide falls apart
and makes a free radical with a single electron.
This highly reactive particle starts the
polymerization process.
To go to a web site and read more click here.
Plastics are polymers made from monomers of
substituted ethene.
Examples include:
Teflon
Plexiglass
Methyl-2-propenoate
tetrafluoroethene
1-methoxy-2-propenal
F
F
F
C
F
CH
C
C
F
F
C C
F
H2C
F
n
H3C
O
O
H
H
C
C
H
COOCH3 n
Monomers used to make synthetic rubber
CH3
H2C
C
Cl
CH
isoprene
CH2
H2C
C
CH
CH2
neoprene
Name these monomers.
2-methyl-1,3-butadiene 2-chloro-1,3-butadiene
The presence of the more electronegative Cl
makes it more polar and less miscible with
other hydrocarbons.
Carbohydrate Polymers – starch, cellulose,
glycogen
monomer + monomer + monomer + monomer
polymer
OH
OH
O
O
+
OH
OH
OH
OH
OH
O
+
OH
OH
OH
OH
+
OH
OH
OH
OH
The orientation of these bonds and the degree of
cross-linking determines what it is.
Typical Fats (Triglycerides)
Linoleic acid, (omega 6)
H
H
glycerol
O
C
CH2
C
CH2
CH2
CH2
CH2
CH2
C
CH2
OH
CH2
H
HO
C
C
H
CH2
CH2
CH2
CH2
CH3
H
H
O
C
CH2
C
C
CH2
CH2
CH2
CH2
C
CH2
OH
HO
CH
Linolenic acid,
H
C
H
CH2
CH2
H
CH2
C
H
(omega 3)
C
CH2
H2C
CH3
OH
O
C
H
CH2
C
C
H
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
HO
CH3
CH2
CH2
CH2
Oleic acid (monounsaturate)
CH2
Typical Fats (Triglycerides)
Linoleic acid, (omega 6)
H
H
glycerol
O
C
CH2
C
CH2
CH2
CH2
CH2
CH2
C
CH2
OH
CH2
H
HO
C
C
H
CH2
CH2
CH2
CH2
CH3
H
H
O
C
CH2
C
C
CH2
CH2
CH2
CH2
C
CH2
OH
HO
CH
Linolenic acid,
H
C
H
CH2
CH2
H
CH2
C
H
(omega 3)
C
CH2
H2C
CH3
OH
O
C
H
CH2
C
C
H
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
HO
CH3
CH2
CH2
CH2
Oleic acid (monounsaturate)
CH2
Soap Making Saponification
H
H
O
C
CH2
C
CH2
CH2
CH2
CH2
CH2
C
CH2
OH
CH2
H
+ NaOH CH
HO
C
C
H
CH2
CH2
CH2
CH2
CH3
H
H
O
C
CH2
C
CH2
CH2
CH2
CH2
C
CH2
OH
+
NaOH
HO
CH
CH2
H
C
H
C
H
CH2
2
C
H
C
CH2
+ NaOH
H2C
CH3
OH
O
C
H
CH2
C
C
H
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3
CH2
CH2
CH2
HO
CH2
Soap Making Saponification
soap
H
H
O
C
CH2
C
CH2
CH2
CH2
CH2
CH2
C
CH2
OH
CH2
H
C
C
H
CH2
CH2
CH2
CH2
HOCH2
CH2
O
C
CH2
C
CH2
CH2
CH2
CH2
CH2
C
CH2
OH
HO
Na
HO CH
CH
CH2
H
C
H
C
H
HO Na
Na
CH3
H
H
glycerol
C
H
C
CH2
H2C
CH3
OH
O
C
H
CH2
C
C
H
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH3
CH2
CH2
CH2
Na HOCH2
HONa
CH2
Most soaps are made from palmitin and
stearin from palm oil and olive oil.
OH
O
C
CH2
CH2
CH2
CH2
H2C
CH2
CH2
CH2
H2C
CH2
CH2
CH2
CH2
CH2
CH2
CH2
CH2
Stearic acid
CH3
CH2
H2C
CH2
CH2
CH3
OH
H2C
CH2
CH2
CH2
C
CH2
CH2
Palmitic acid
CH2
CH2
CH2
O
Show, using structural diagrams, how
sodium stearate is made. See pg. 134
There are 2 classes of fats which are essential in
the human diet because they cannot be
biosynthesized by the human body.
These fats are called essential fatty acids (EFA)
and as the name implies they contain the
carboxyl functional group (COOH).
They fall into 2 categories omega 3 and omega
6. All of these essential fatty acids are
unsaturates.
Essential omega 3 fatty acids include:
α-linolenic acid (ALA),
eicosapentaenoic acid (EPA), and
docosahexaenoic acid (DHA).
alpha-linolenic acid (18:3, ALA),
eicosapentaenoic acid (20:5, EPA), and
docosahexaenoic acid (22:6, DHA).
These three polyunsaturates have either 3, 5
or 6 double bonds in a carbon chain of 18, 20
or 22 carbon atoms, respectively.
All double bonds are in the cis-configuration,
i.e. the 2 H atoms are on the same side of the
double bond.
ALA – alpha-linolenic acid (18:3) (18 carbons,
3 double bonds at positions 3,6,9 from the
terminal methyl end; found in (flax seed oil)
EPA – Eicosahexaenoic acid (20:5) 3,6,9,12,15
DHA - Docosohexanoic acid (22:6)
3,6,9,12,15,18 ?
All three found in seaweed, cold water fish
Shortening is a semisolid fat used in food
preparation, especially baked goods, and is
so called because it inhibits the formation
of long gluten strands in wheat-based
doughs, giving them a "short" texture (as in
shortbread).
Shortening can be made from animal fat
(lard), but is more commonly a
hydrogenated vegetable oil that is solid at
room temperature.
Shortening has a higher smoke point than
butter and margarine, and it has 100% fat
content, compared to 80% for butter and
margarine. Crisco, a popular brand, was
first produced in 1911.
Despite its worldwide usage and
availability, vegetable shortening is
believed to be damaging to human health
since it generally contains trans fats.
Denmark banned it from foods in 2003.
Lard - rendered and clarified pork fat, the
quality of which depends on the area the fat
came from and the method of rendering. The
very best is leaf lard, which comes from the fat
around the animal's kidneys.
The Nutritional Value for: lard
Carbs Protein Cholesterol Weight
Fat
Saturated Fat
Quantity
(grams) (grams) (milligrams) (grams) (grams)
(grams)
1 cup
0
0
195
205
205
80.4
1 tbsp
0
0
12
13
13
5.1
Toward the late 20th century lard began to be regarded as less
healthy than vegetable oils such as olive and sunflower due to
its high saturated fatty acid and cholesterol content.
Tallow is a solid fat extracted from the tissues
and fatty deposits of animals, especially from
suet (the fat of cattle and sheep).
Pure tallow is white, odorless and tasteless; it
consists chiefly of triglycerides of stearic
(CH3(CH2)16COOH ), palmitic
(CH3(CH2)14COOH ), and oleic acids (18
carbon, monounsaturated, omega 9 fatty acid).
Draw the carbon skeleton.
A triglyceride is made by an esterification
involving 1,2,3-propantriol and 3 fatty acids.
Show how a triglyceride is made from oleic,
stearic and palmitic acids.
Tallow is usually obtained commercially by
heating suet (the hard fatty tissues around the
kidneys of cattle and sheep) under pressure in
closed vessels.
Tallow is used to make soap and candles. It was
formerly in common use as a lubricant.
but·ter (bŭt'ər)
n.
1.A soft yellowish or whitish emulsion of butterfat, water, air, and
sometimes salt, churned from milk or cream and processed for use in
cooking and as a food.
The Nutritional Value for: butter
Description Quantity
salted
salted
salted
1 PAT
1 tbsp
1/2 cup
unsalted
unsalted
unsalted
1 PAT
1 tbsp
1/2 cup
Cholesterol Weight
Fat
Saturated Fat
(milligrams) (grams) (grams)
(grams)
11
5
4
2.5
31
14
11
7.1
247
113
92
57.1
11
31
247
5
14
113
4
11
92
2.5
7.1
57.1
canola oil (kə′nōl·ə ′öil)
(food engineering) An edible vegetable oil
derived from rapeseed that is low in saturated
fatty acids (less than 7%), high in monosaturated
fatty acids (60%), and high in polyunsaturated
fatty acids (30%).
Here's a comparison of some to the more
common fats and oils.
The lower the saturated fat, the better
For more information click here