salicyl alcohol acetyl salicylic acid. saturated carbon chains c c-c c-c-c
TRANSCRIPT
Salicyl alcohol acetyl salicylic acid
Saturated carbon chains
C
C-C
C-C-C
CATENATION: OLD (CHEM 1):
Valence
IONIC COVALENT
CH3
morphine = Acylated morphine=Heroine
CH3
Name the following alkanes:
C2H6
C4H10
Review the work from your notebook from the past week.
Spend 5 minutes writing/reflecting about what you learned. Include specific examples.
Saturated carbon chains
ROOT NAME EXAMPLE
C
C-C
C-C-C
C-C-C-C
5 C
6 C
7-C
8 C
9 C
10 C
-OH is the alcohol functional group
Generic alcohol can be written R-OH
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
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.
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 are a group of water INSOLUBLE compounds that include Fats Oils Waxes
Your cells are made of a lipid bi-layer.
In a strong base or acid water , H-OH, willbreak apart the
R-COO-RInto
R-COOH and R-OH
Carboxylic Acid and Alcohol
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
Review the work from your notebook from the past week.
Spend 5 minutes writing/reflecting about what you learned. Include specific examples.
Review the work from your notebook from the past week.
Spend 5 minutes writing/reflecting about what you learned.
Insoluble in water
~Apple wax C27H56
Broccoli C29
Tobacco C31
Low boiling points compared to similar weight molecules.
(only London/Van der Waal’s dispersion forces)
Branched alkanes have lower boiling points than straight.
More spherical molecules are more difficult to induce dispersion forces. (=weaker)
Pentane36
2-methyl butane 28 (isopentane)
2,2 dimethyl propane10
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
2- butene
2-3 dimethyl butane
Cis = same side
Cis 1,2 dimethlycyclopentane
Trans = opposite side
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
Substitution reactions
A halogen replaces a hydrogen
R-H + Cl-Cl R-Cl + H-Cl
Chloroethene
(Vinyl chloride)
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Family of organic acids.Weak acids
Functional group COOH
or CO2H
Carbonyl C=O Hydroxyl -OH
A carboxylic acid derivative replaces the -OH (hydroxyl) group with another functional group.
Examples:• esters• acyl halides
Alkane = ethaneCarboxylic acid =
ethanoic acid
Replace the final e of the alkane with “–oic” add the word “acid”
Alkane = benzeneCarboxylic acid =Benzenoic acid(benzoic)
The hydroxyl group -OH of the carboxylic acid is replaced by
-OR’
R first-OR’ next. Change ”ic” to “ate”
Our favorite results so far:
Alcohol Carboxylic acid Name Odor
C8H8O2 COOH (Ester)
Alkanes, Alkanes, they're driving me insane.
1) pi bonds ( π ) are broken
( π )1) sigma bonds ( σ )
formed to 2 new atoms
Hydrochlorination
Hydration
Bromination
Hydroxylation
Hydrogenation
Br2 to an alkeneCl2 to an alkeneIThe 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
Reaction of :1-hexene with bromine.
Cyclopentene with bromine.
1) pi bonds ( π ) are broken
( π )1) sigma bonds ( σ )
formed to 2 new atoms
Hydrochlorination
Hydration
Bromination
Hydroxylation
Hydrogenation
Water H- OH adds to the double bond of an alkene.
An acid is required to act as a catalyst (H+)
ProblemAcid catalyzed hydration of
2-butene
Br2
H2O
H2
HBr
Problem:Hydration of 2-methyl-2-butene
Addition products of unsymmetric reagents to unsymmetric alkenes are called regioisomers.
REGIOSPECIFICREGIOSELECTIVE
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.
problems1-butene + HBrHydration of 1-chloro-2-butene (using an acid
catlalyst)
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.
Electrophile: E+
electron poor reactant; seeks electrons
Nucleophile: Nu-
electron rich reactant; forms bonds by donating electrons. (to electrophiles)
How many sigma bonds, and how many pi bonds are there?
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.
Ethyne (Acetylene)+ Br2
With a Ni or Pt catalyst
Alkynes are fully hydrogenated
C2H2 + H2
With palladium catalyst (Lindlar’s catalyst)
Only 1 mole of H2 is added and you end up with a cis alkene
Ni
CH3CCH + H-Br
Follow Markovinkov for each step.
3.40 a-f
3.42 a-e
3.53a
Alcohols ACETIC PROPIONOIC BENZOIC
SALICYLIC
Methyl
Ethyl
Propyl
Isoamyl
Octyl
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
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.
Molecules with empirical formula CH2O they are ‘hydrates’ of Carbon
Examples: glucose, fructose, dextrose Uses:
cell energy requirements cell structures
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
Aldehyde
Ketone
Aldose Ketose
Describe an isomer
Structrual = different bond pattern
Stereoisomers = same bond pattern
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.
Build chlro-bromo methanol. (use different color for the 2 halogens)
Determine if you have the R, or S version1. Locate the sterocenter.2. Assign priority based on molecular weight to each
attached atom.3. Orient the molecule so the lowest priority is
pointed away from you.4. Trace your finger in a circle beginning with the
highest priority to the lowest priority.5. IF the circle is clockwise, you have an R isomer. if the circle is counterclockwise you have an S
isomer.
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- butanol2-propanol
Stereocenter is a carbon with 4 unique attachements.
Build/Draw 2 chlorobutane 3 chloro cyclohexene
Identify the stereocenter in each molecule
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.