Chemistry 102 Week 2 lecture. Starting chapter 14 Organic and Biochemistry for the Allied Health Fields Dr Mark Deming. Organic Chemistry Part II. Compounds with O and N and sometimes S and P. Next few chapters compounds with OXYGEN.
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Carboxylic acids Esters
Connections to O
1. Name the longest chain to which a hydroxy group ( -OH) is attached and end in -ol
2. Number the longest chain to give the lowest number to the carbon with the hydroxy
3. Put location of hydroxy in front of root name
4. Locate and name any side groups in prefix
Step 1: Name the longest chain to which the –OH group is attached. Use the alkane name of the chain, drop the –e ending, and replace it with –ol.
Step 2: Number the longest chain to give the lowest number to the carbon with the –OH.
Step 3: Locate the –OH position.
6 5 4 3 2 1
Naming Alcohols, cont.
Step 4: Locate and name any other groups attached to the longest chain.
Step 5: Combine the name and location of other groups, the location of the –OH, and the longest chain into the final name.
6 5 4 3 2 1
Stimulates health andgrowth of hair, nails, skin cells. Helps eyes bybringing oxygen tobody tissues. Can help eliminatedandruff. May aid in preventing hair loss.
Alcohol, poly functional, highly conjugated 14 atoms (16 atoms)
Highly conjugated 14 atoms (16 atoms)
14+ carbons conjugated becomes colorful
This compound is a pale yellow solid named after latin flavis (yellow)
primary, secondary, tertiary
(primary, secondary, tertiary, aromatic)
1-aromatic 2-primary 3-aromatic 4-tertiary 5-secondary 6-primary 7-secondary
8-secondary 9-primary 10-aromatic 11-primary 12-tertiary 13-tertiary 14-secondary
Caution: these molecules were made up and may not be biologically relevant
Ionicmust be an ionic compound (made of full charges)starts with metal or ammonium (acid-base salts)
Super H-bondingH-bonding + polar + partially ionizescarboxylic acid COOH
from a O-H > N-H to a lone pair on O: > N:Amide (with H) > alcohol (OH) > amine (NH)
net polar moleculeester > amide (no H) > aldehyde > ketone > ether
London Dispersion Forces (LDF)Non polar molecule (all molecules) aromatic > -ynes > -enes > -anes (only C,H)
Same force higher mass higher mp, higher bp, lower vapor pressure
Same approx. mass higher force higher mp, higher bp, lower vapor pressure
= Energy of Attraction (additive)
Energy of Disruption
High TEMP(higher velocity)
Low Mass (MW) High Vibration High Velocity Starts with at given temp.(same force)High Mass (MW) Low Vibration Low Velocity
Has OH or NH
Increase Energy of Attraction
Increase Energy of Disruption
Has O or N
Low TEMP(lower velocity)
All molecules have LDF
Polar if has O or N
H-bonding if O-H or N-H to O or N
Alcohols have LDF and are polar and can both give and receive an H-bond
Ethers are polar but can only receive an H-bond
Alkane likeNon PolarHydrophobic
Important: Expected to knowRule of thumb: Each OH can make soluble 3 carbons
Solubility of alcohols in water
Four carbons is at the edge of visual solubility
Remember that solubility means dissolve in (or mix with) another chemical
Fig. 13-2, p.419
Note: C3 and C2O are about the same weight, both have 3 big atoms near each other in the table.
Difference must be type of IMF.
In this chapter you are responsible for:
Note: other alcohol reactions we will see in future chaptersChapter 16- aldehydes and ketones react with alcohols to form acetals and ketalsChapter 17- carboxylic acids react with alcohols to become esters
CO2 + H2O
C + H2O
or CO + H2O
( losing H20 )
If primary (1º)
If secondary (2º)
If tertiary (3º)
Dehydration of alcohols to give ethers
Dehydration of alcohols to give alkenes
Oxidation of Primary (1º) alcohol
Oxidation of secondary (2º) alcohol
Oxidation of Tertiary (3º) alcohol
NO REACTION – NADA – NOTHING – NO WAY
Elimination Reaction -remove a molecule
Elimination of H2O to form double bond
Elimination of H2O to from 2 alcohols form an ether
Elimination Reaction of an Alcohol
to form alkenes
The removal of water (dehydration) from an alcohol is an elimination reaction and produces an alkene.
Strong Acid Catalyst
The alcohol is usually in low concentrations to avoid ether formation
Dehydration to form Ethers.
Under slightly different conditions, a dehydration reaction can occur between two alcohol molecules to produce an ether.
The alcohol is usually in high concentration and lower temperature to avoid alkene formation
Remember that Oxidation:
Is the gain of oxygens or the loss of hydrogens at a carbon.
Usually done with a chemical that will itself get reduced called an oxidizing agent: and we will abbreviate it with [O]
Note: most strong oxidizing agents will make the reaction go all the way to the carboxylic acid
Alcohol Reactions, cont.
Primary alcohol oxidation
Secondary alcohol oxidation
(The oxidizing agent)
These are the reactants
Fig. 13-7a, p.423
Chromate is reduced (green-grey)
When mixed the products are in the second tube
Fig. 13-7b, p.423
• Methanol (wood alcohol) CH3OH.
• Useful as a solvent and industrial starting material.
• Highly toxic, causes blindness and/or death.
Ethanol (ethyl alcohol, grain alcohol, drinking alcohol)
Useful as a solvent, industrial starting material, fuel (gasohol), and found in alcoholic beverages. Moderately toxic.
NON RENEWABLEFrom etheylene
RENEWABLEfermentation of carbohydrates (corn) by yeast (biological)
2-propanol (isopropyl alcohol) is the main component of rubbing alcohol.
1,2,3-propanetriol (glycerol, glycerin) is used as a food moistening agent (nontoxic) and for its soothing qualities (soaps).
Don’t need to know for test
Antifreezes1,2-ethanediol (ethylene glycol).
1,2-propanediol (propylene glycol).
Phenols and their uses:
In a dilute solution, phenol is a disinfectant.
Phenol derivatives used as disinfectants
Phenol derivatives used as antioxidants in food
BHT (butylated hydroxy toluene)
BHA (butylated hydroxy anisole)
OXYto smallest group
Ethers There is NO ending name
Naming ethers – the –O-R group is called an alkoxy group. The –yl ending of the smaller R group is replaced by –oxy.
The smallest group attached to O is named as an alkoxy side group with the O
The Common naming of simple ethers is in some places preferred and are widely used.
Common Names of Ethers. – Name each group attached to the O as a side group and attach “ether” as a separate word to the end.
Ethers –Common Names
Heterocyclic rings contain atoms other than carbon in the ring.
Properties of Ethers
Much less polar than alcohols.
More soluble in water than alkanes, but less soluble than alcohols.
Low boiling and melting points because of the inability to hydrogen bond between molecules.
Like alkanes, ethers are inert and do not react with most reagents.
Also like alkanes, they are highly flammable.
Thiols: the –SH (sulfhydryl, mercaptan) group
Most distinguishing characteristic is their strong and offensive odor.
Ethanethiol – added to natural gas.
1-propanethiol – odor in garlic and onions.
Trans-2-butene-1-thiol – odor associated with skunks.
[O] (oxidation) -- (lose H’s as water)
Found in proteins, enzymes and hair to retain specific shape
M= Hg2+ or Pb2+
Hg2+ or Pb2+
Accumulates over lifetime
Dimethyl mercury is nonpolar and will reside in fatty tissues and lymphatic system and cell walls. It is slowly released doing damage. Children affected more!
Distorts shape of proteins, enzymes making them inactive. Retained in hair
Oxidation forms disulfide (-S-S-) linkages which are important structural features of some proteins.
Reacts with heavy metals (Pb2+, Hg2+) to form insoluble compounds, with adverse biological results. This is why lead and mercury are always in the news as pollutants.
Why is this so bad?
Implied from Ch 16 and Ch 15
Note: We can make these connections in a test tube but biologically there is an enzyme to make and break each connector above.
These hold pieces or parts together but not bonded, Easier to break
Compounds with two or more functional groups. Functional groups determine chemical properties of compounds.