Transcript Organic Chemistry

ORGANIC CHEMISTRY

Salicyl alcohol
acetyl salicylic acid
ORGANIC NAMING
Saturated carbon chains
C
C-C
C-C-C
CATENATION:
OLD (CHEM 1):

Valence
ORGANIC (NEW):
IONIC
BONDING
COVALENT
FUNCTIONAL GROUPS
GOLDEN TRIANGLE
MORPHINE
CODEINE
MORPHINE
CH3
THE HERO DRUG.
morphine =
Acylated morphine=Heroine
CH3
WARM UP

Name the following alkanes:

C2H6

C4H10
WK 1 REFLECTION
Review the work from your
notebook from the past
week.
Spend 5 minutes
writing/reflecting about
what you learned.
Include specific
examples.
ORGANIC NAMING
Saturated
carbon chains
C
C-C
C-C-C
C-C-C-C
5C
6C
7-C
8C
9C
10 C
ROOT NAME
EXAMPLE
-FUNCTIONAL GROUPS
-OH is the alcohol
functional group
 Generic alcohol
can be written ROH
 R, represents a
carbon chain of
some sort

There is an interesting legend surrounding the discovery of soap
making. This legend accords the discovery of soap to the Romans so it
must be a Roman legend to confront the Celtic claim to soap making.
Probably both of these inventive peoples discovered soap making
independently.
The legend says soap was first discovered by women washing clothes
along the Tiber River at the bottom of Sapo Hill. The women noticed the
clothes became cleaner with far less effort at that particular location.
What was happening? The ashes and the grease of animals from the
sacrificial fires of the temples situated on the top of Sapo Hill mixed
with the rain, making soap which ran down the slope in the streams of
rain water giving the women a wash day bonus.
You can see at a glance saponification, the chemical name for the soap
making reaction, bears the name of that hill in Rome long ago, which
caused one Roman washer women to comment to another, "My wash is
cleaner than yours".
Organic compounds are those that are made mostly of carbon
ORGANICS, LIPIDS, AND SOAPS
ORGANICS



Carbon chain molecules, with hydrogen filling up the
extra bonding areas.
Can be one carbon, 2,3,….20…
Non carbon parts are known as functional groups.
ESTERS…THE RCOOR FUNCTIONAL
GROUP


What are esters?
Esters are derived
from carboxylic
acids. A carboxylic
acid contains the COOH group, and in
an ester the
hydrogen in this
group is replaced by
a hydrocarbon
group of some kind
LIPIDS--- A TYPE OF ESTERS

Lipids are a group of
water INSOLUBLE
compounds that
include




Fats
Oils
Waxes
Your cells are made
of a lipid bi-layer.
HYDROLIZATION OF AN ESTER
In a strong base or acid
water , H-OH, will
break apart the
R-COO-R
Into
R-COOH and R-OH

Carboxylic Acid
and
Alcohol
SAPONIFICATION

Hydrolyzing fats in the presence of
a base

Like NaOH…sodium hydroxide.
Soaps are alkali metal salts
(Na, K, or Li)
of carboxylic “fatty” acids.
When put into a NaCl mixture, the
soap separates from the glycerol
WK 2 REFLECTION
Review the work from your
notebook from the past
week.
Spend 5 minutes
writing/reflecting about
what you learned.
Include specific
examples.
WK 3 REFLECTION
Review the work from your
notebook from the past
week.
Spend 5 minutes
writing/reflecting about
what you learned.
PROPERTIES OF ALKANES

Insoluble in water
~Apple wax
C27H56
Broccoli C29
Tobacco C31
PROPERTIES OF ALKANES

Low boiling points compared
to similar weight molecules.
(only London/Van der Waal’s
dispersion forces)
Branched alkanes have
Pentane
lower boiling points than
straight.
2-methyl butane
(isopentane)
More spherical molecules
are more difficult to
2,2 dimethyl propane
induce dispersion
forces. (=weaker)
36
28
10
SOURCES OF ALKANES
Petroleum
-liquid mixture of organic
compounds: mostly
alkanes and cycloalkanes.

From decayed animal and
vegetable matter
-

Parts are separated by
distillation
-
Natural Gas
Gas mixture of methane
(80%) and ethane (10%)
and other alkanes
Often found near deposits
of petroleum
BUILD

2- butene
2-3 dimethyl butane
CIS-TRANS ISOMERISM
(GEOMETRIC ISOMERISM)
Cis = same side
Cis 1,2
dimethlycyclopentane
Trans = opposite side
REACTIONS OF ALKANES
COMBUSTION/OXIDATION
Oxidation of an alkane,
replace C-H bond(s)with C-O bond(s)
Alkanes used as fuels
Alkane + O2  CO2 + H2O
- ∆H
heat energy released
HALOGENATION OF ALKANES
Substitution reactions
Chloroethene
A halogen replaces a
hydrogen
R-H + Cl-Cl  R-Cl + H-Cl
(Vinyl chloride)
3 | 32
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A TRIGONAL CARBON SHOWING THREE SP2
HYBRID ORBITALS IN A PLANE WITH A 120°
BETWEEN THEM.
3 | 33
SCHEMATIC FORMATION OF A
CARBON-CARBON DOUBLE BOND
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3 | 34
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Company.2All rights2reserved.
THE BONDING IN ETHYLENE CONSISTS OF ONE SP -SP
CARBON-CARBON Σ BOND, FOUR SP2-S CARBON-HYDROGEN Σ
BONDS, AND ONE P-P Π BOND.
3 | 35
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IN THE LIVER, ß-CAROTENE IS CONVERTED INTO
VITAMIN A FIRST AND THEN INTO 11-CISRETINAL.
4 | 36
BENZENE--BALL-AND-STICK
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Company. All rights reserved.
4 | 37
Copyright © Houghton Mifflin
Company. All rights reserved.
AN ORBITAL REPRESENTATION OF THE BONDING
IN BENZENE.
CARBOXYLIC ACIDS (AND DERIVATIVES)
Family of organic acids.
Weak acids
Functional group COOH or
CO2H
CARBONYL + HYDROXYL = CARBOXYL
Carbonyl C=O
 Hydroxyl -OH

A carboxylic acid
derivative replaces
the -OH (hydroxyl)
group with another
functional group.
Examples:
•
esters
•
acyl halides
ACID NOMENCLATURE
Replace the final e
of the alkane with
“–oic” add the
word “acid”
Alkane = ethane
Carboxylic acid =
ethanoic acid
ACID NOMENCLATURE (AROMATIC)
Alkane = benzene
Carboxylic acid =
Benzenoic acid
(benzoic)
ALIPHATIC = NOT AROMATIC
ESTERS
R-O-R’
The hydroxyl group -OH of the carboxylic acid
is replaced by
-OR’
NAMING ESTERS
R first
-OR’ next. Change ”ic” to “ate”
ESTERIFICATION: WHAT WORKS?
Our favorite results so far:
Alcohol
Carboxylic acid
Name
Odor
FORMULA AND FUNCTIONAL GROUP
C8H8O2
COOH (Ester)
ORGANIC NAMES
Alkanes, Alkanes, they're driving me insane.
REACTIONS OF ALKENES: ADDITION
1)
1)
pi bonds ( π ) are
broken
(π)
sigma bonds ( σ )
formed to 2 new atoms
TYPES OF ADDITION REACTIONS

Hydrochlorination

Hydration

Bromination

Hydroxylation

Hydrogenation
HALOGENATION (BROMINE OR CHLORINE OR
IODINE)
Br2 to an alkene
Cl2 to an alkene
I
The addition of a single halogen to each carbon of
the double bond.
The reaction is spontaneous, occurs at room
temperatures, and needs no additional energy
input.
electrophilic addition
PROBLEM
Reaction of :
1-hexene with bromine.
Cyclopentene with bromine.
REACTIONS OF ALKENES: ADDITION
1)
1)
pi bonds ( π ) are
broken
(π)
sigma bonds ( σ )
formed to 2 new atoms
TYPES OF ADDITION REACTIONS

Hydrochlorination

Hydration

Bromination

Hydroxylation

Hydrogenation
HYDRATION (ADDING WATER)
Water H- OH adds to the double bond of an
alkene.
An acid is required to act as a catalyst (H+)
Problem
Acid catalyzed hydration of
2-butene
SYMMETRIC / UNSYMMETRIC REAGENTS
Br2
H2 O
H2
HBr
Problem:
Hydration of 2-methyl-2-butene
Addition products of unsymmetric reagents to unsymmetric
alkenes are called regioisomers.
REGIOSPECIFIC
REGIOSELECTIVE
MARKOVNIKOV’S RULE
Determines where an unsymmetrical reagent will
react. Which regioisomer will be favored.
The electronegative part bonds to the carbon with
the least number of hydrogens.
problems
1-butene + HBr
Hydration of 1-chloro-2-butene (using an acid
catlalyst)
PRACTICE PROBLEMS REACTIONS
3.8 (pg 85)
3.9 (pg 85)
3.10 (pg 86)
3.11 (pg 88)
look up the following terms:
electrophile , nucleophile, and carbocation.
ELECTROPHILIC ADDITION
Electrophile: E+
electron poor reactant; seeks electrons
Nucleophile: Nuelectron rich reactant; forms bonds by donating
electrons. (to electrophiles)
DRAW ETHYNE
How many sigma bonds, and how many pi bonds are there?
ADDITION TO ALKYNES: HALOGENATION
Ethyne
(Acetylene)
+ Br2
In a multistep process,
bromine is added to
all the pi electrons.
First mole of Br2
produces a trans
product.
Second mole of Br2
produces a fully
halogenated procudt.
ADDITION TO ALKYNES: HYDROGENATION
With a Ni or Pt catalyst
Alkynes are fully
hydrogenated
Ni
C2H2 + H2 
With palladium
catalyst (Lindlar’s
catalyst)
Only 1 mole of H2 is
added and you
end up with a cis
alkene
UNSYMMETRIC TRIPLE BONDS
USE MARKOVNIKOV’S RULE
CH3CCH + H-Br
Follow Markovinkov
for each step.
3.29 A, B, C
3.40 a-f
3.42 a-e
3.53a
CLOVES NUTMEG AND PEPPERS
ESTERS
Alcohols
Methyl
Ethyl
Propyl
Isoamyl
Octyl
ACETIC
PROPIONOIC
BENZOIC
SALICYLIC
ACTIVATED CHARCOAL
Charcoal is used as a
filtering material
 The charcoal has a very
large surface area per unit
mass


1g has 500-1000m2 of
reactive surface area
ACTIVATED CHARCOAL
Has an affinity for organic compounds, gases,
halogens.
 Great to remove contaminants.

Charcoal filtration of Grape Juice.
Sketch your lab set up, describe the procedures,
and results.

CARBOHYDRATES
Molecules with empirical formula CH2O they are
‘hydrates’ of Carbon
 Examples: glucose, fructose, dextrose

Uses:
cell energy requirements
cell structures
CARBOHYDRATES

Monosaccharides (ex. Glucose)
 Simples
carbohydrates
 Are the building blocks of other carbohydrates

Disaccharides
2

mono-sacs bonded together
Polysaccharides
 Large
carbohydrates, polymers built of many monos
FUNCTIONAL GROUPS
Aldehyde
Ketone
Aldose
Ketose
ISOMERS
Describe an isomer
Structrual = different bond pattern
Stereoisomers = same bond pattern
STEREOISOMERS
Two 3-d forms of a molecule with different
orientations in space.
Stereoisomers are chiral. (Show handedness)
Try to superimpose your left and right hand.
NAMING STEREOISOMERS

Build chlro-bromo methanol. (use different color for the 2
halogens)

Determine if you have the R, or S version
Locate the sterocenter.
Assign priority based on molecular weight to each attached
atom.
Orient the molecule so the lowest priority is pointed away
from you.
Trace your finger in a circle beginning with the highest
priority to the lowest priority.
IF the circle is clockwise, you have an R isomer.
if the circle is counterclockwise you have an S isomer.
1.
2.
3.
4.
5.
CHIRALITY
The mirror image of a chiral molecule cannot
be superimposed on the molecule itself.
(an achiral molecule can be superimposed)

Build the following molecule(s).
2- butanol
2-propanol

Stereocenter is a carbon with 4 unique
attachements.

Build/Draw
2
chlorobutane
 3 chloro cyclohexene
Identify the stereocenter in each molecule
PROPERTIES OF STEREOISOMERS

Stereoisomers have identical chemical and
physical properties.
Stereoisomers are OPTICALLY active.
 Our enzymes typically only react with 1 of the 2
stereoisomers. The binding sites for enzymes
are based on a specific chirality.
