Professional Documents
Culture Documents
Ex.
• IUPAC Nomenclature
-for alcohols containing a single hydroxyl
group
o Rule 1: Name the longest carbon chain to
which the hydroxy group is attached. The
chain name is obtained by dropping the
Important Commonly -ingestion of this: lead to liver cirrhosis,
memory loss, addiction
Encountered Alcohols
6 commonly encountered alcohols: -Proof - percentage of alcohol present divided
1. Methyl Alcohol (Methanol) by 2
-one carbon atom and one -OH group
-simplest alcohol
-colorless liquid
-good fuel for internal combustion engines
-methyl alcohol fuel fires are easier to
put out than gasoline fires bc water
mixes with and dilutes methyl alcohol).
-has excellent solvent properties
-solvent of choice for paints, shellacs,
varnishes
-AKA wood alcohol
-terminology draws attention to an
early method for its preparation -
heating of wood to a high temperature 3. Isopropyl Alcohol (2-Propanol)
in the absence of air. -70% isopropyl and 30% water - marketed as
-drinking this is very dangerous the rubbing alcohol.
-it is oxidized by the liver enzyme -has a rapid evaporation rate that creates a
alcohol dehydrogenase to the toxic dramatic pulling effect when it is applied to
metabolites formaldehyde (for the skin, hence its use for alcohol rubs to
embalming) and formic acid. combat high body temperature.
Formaldehyde - can cause -has bitter taste
temporary or permanent -toxicity is twice that of ethyl alcohol
blindness -fewer fatalities as it often induces
Formic acid - causes acidosis vomiting and thus doesn't stay down to
long enough to be fatal.
2. Ethyl Alcohol (Ethanol) -large amount (about 150mL) of ingested
-safe to ingest but at a certain degree isopropyl alcohol can be fatal
-2-carbon monohydroxy alcohol -death occurs from paralysis of the CNS.
-alcohol present in alcoholic beverages
-commonly known as alcohol or drinking 4. Ethylene Glycol (1,2-Ethanediol)
alcohol 5. Propylene glycol (1,2-Propanediol)
-like methanol, it is oxidized by the liver -two simplest alcohols possessing 2 -OH
enzyme alcohol dehydrogenase groups
-Acetaldehyde - first oxidation product, -examples of diol
largely responsible for symptoms of -also classified as glycols
hangover, further converted into acetic -glycol - diol in which the 2 -OH groups
acid are on adjacent carbon atoms.
-oxidation products are less toxic than those
of methyl alcohol
-extracted from grains (ex. Rice, etc.)
-may cause birth defects to babies (when -both are colorless odorless, high-boiling
ingested during pregnancy) liquids that are completely miscible with
-Fetal Alcohol Syndrome water.
-major uses - main ingredient in automobile
"year-round" antifreeze and airplane "de-
icers"
-Ethylene glycol
-extremely toxic when ingested
-oxidized by liver enzymes into oxalic
acid
Oxalic acid -calcium salt,
crystallizes in the kidneys leading
to renal problems, enveloped-
-decrease of IQ points of babies shaped crystals under microscope
-Propylene glycol
-essentially nontoxic and has been used Intramolecular Alcohol Dehydration
as a solvent for drugs. -dehydration reaction
-chemical reaction in which the components
6. Glycerol (1,2,3-Propanetriol) of water (H and OH) are removed from a
-example of triol single reactant or from 2 reactants (H from
-AKA glycerin one and OH from the other).
-clear, thick liquid that has the consistency of -both water components are removed from the
honey same molecule.
-molecular structure - 2 -OH groups on 3 -reaction conditions: temperature of 180°C and
different carbon atoms. presence of sulfuric acid as a catalyst
-dehydration product: an alkene
Structural Characteristics of
Phenols
Phenols -Physical and Chemical Properties of Phenols
-organic compound in which an -OH group is • Generally low-melting solids
attached to a carbon atom that is part of an • Oily liquids at room temperature
aromatic carbon ring system. • Most of them are only slightly soluble in
water
• Many have antiseptic and disinfectant
properties
• Simplest phenol - phenol itself, is a colorless
solid with a medicinal odor
-general formula: Ar-OH, where Ar represents aryl
• Melting point is 41°C
group
• More soluble in water that are most other
-aryl group - an aromatic carbon ring system from
phenols
which one hydrogen atom has been removed.
-hydroxyl group - thus the functional group for both
phenols and alcohols Alcohol Phenols
Thiols
-sulfur analogs of alcohols
-contain -SH functional groups instead of -OH
functional groups
-sulfhydryl group - thiol functional group, SH
functional group
-organic compound in which a sulfhydryl is bonded
to a saturated carbon atom
-older term is mercaptans
-Nomenclature
• Thiols are named in the same way as
alcohols in the IUPAC system, except that
the –ol becomes -thiol. The prefix thio-
indicates the substitution of a sulfur atom
for an oxygen atom in a compound
• As in the case of diols and triols, the -e at the
end of the alkane name is also retained for
thiols.
-Properties
Aldehydes and Ketones
Thursday, December 9, 2021
7:50 AM
Aldehydes
-have a carbonyl group bonded to a carbon atom on
one side and a hydrogen atom on the other side
• Aliphatic ketones are named substitutively
by replacing final -e of the name of the
Carbonyl group - carbon with double bond
with oxygen corresponding alkane with -one.
-Formaldehyde - an exception bc it has hydrogen
• The chain is then numbered in the way that
gives the carbonyl carbon atom, the lower
atoms on both sides
possible number, and this number used to
designate its position.
Ketones
-have carbonyl group bonded to carbon atoms on Common functional group names for ketones
both sides are obtained simply by separately naming the
two groups attached to the carbonyl group
and adding the word ketone as a separate
word.
Nomenclature of Aldehydes and • Some ketones have common names that are
Ketones retained in the IUPAC system
• Aliphatic aldehydes are named
substitutively in the IUPAC system by
replacing the final -e of the name of
corresponding alkane with -al
• Since the aldehyde group must be at the end
of carbon chain, there is no need to indicate
its position.
-When other substituents are present the
carbonyl group carbon is assigned position 1. Physical Properties
• Common names are derived from the -the carbonyl group is a polar group; therefore,
common names for the corresponding aldehydes and ketones have higher boiling
carboxylic acids, and some of them are point than hydrocarbons of the same molecular
retained by IUPAC as the acceptable names weight.
-they cannot have strong hydrogen bonds
between their molecules, they have lower boiling
points that the corresponding alcohols
-specific example:
Synthesis of Ketones
Ketones (and aldehydes) by Ozonolysis of
Alkenes
-Ozonolysis - organic reaction where the
unsaturated bonds of alkenes, alkynes or azo
compounds are cleaved with ozone.
Carboxylic Acids, Esters, And other Acid
Derivatives
Thursday, December 16, 2021
7:22 AM
• Dicarboxylic Acids
-2 carboxylic groups
o For these compounds, both ends of a chain
will end with a –COOH group. The parent
• General formula chain is the one that involves both –COOH
groups.
o The parent chain is named as an alkane and
the term “dioic acid” is added afterwards to
indicate the diacid structure.
-R-radicals/carbon chain
-C with double bond O single bond OH- makes
it a carboxylic acids
-2-
Bromobutanedio
ic acid
-simplest - formic acid, only one C
-benzoic acid - parent name
• For common names carboxylic acids and -for IUPAC naming - O-atom of the carbonyl
diacids, substituents are often numbered group is treated as an "oxo" substituent (not
using Greek system as a ketone) and the molecule is called 2-
oxopropanoic acid
• Unsaturated Acids
-possess a unit of unsaturation (double/triple
C-C bond) in the structure
-Most common:
• Hydroxy Acids
Physical Properties of Carboxylic
Acids
• Most polar functional group so far
-the presence of the carbonyl group next the
OH causes the O-H bond to be even more
polar and reactive
• Aromatic carboxylic acids can be made by
oxidizing alkyl-substituted aromatic
molecules
Structure of Esters
Esters
-carboxylic acid derivatives having an alkoxy group IUPAC Nomenclature of Esters
instead of a hydroxyl group. 1. The name for the alcohol portion comes
first; name the alkyl part of the alcohol.
Present the alkyl name separate from the
remainder of ester name.
2. The carboxylic portion is named as if it
were deprotonates changing the "-ic acid"
to "ate" or "oate"
Preparation of Esters
Esterification Reactions
-condensation reactions involving carboxylic acids
and alcohols
Other examples:
Anhydride
-compound derived from another (such as an acid)
by removal of the elements of water
Acid Anhydride
-contains 2 molecules of an acid, with a loss of a
molecule of water.
-addition of water regenerates 2 molecules of
carboxylic acid 2. Acyl Chlorides also react with carboxylic
acid to give acid anhydride
Nomenclature
-"acid" is changed to "anhydride" (in common and Heating Carboxylic Acids with ZnO
IUPAC) -acid anhydride can be prepared from heating
simple carboxylic acids with Zinc Oxide
-oxidation reaction
Mixed Anhydrides
-anhydrides composed of two different acids
-named using names of individual acids
-alphabetize the names for both acids and replacing
the word acid with the word anhydride
Symmetrical Anhydrides
-word "acid" from carboxylic acid to the word Heating Dicarboxylic Acids
"anhydride" -Certain cyclic anhydrides can be prepared by
heating dicarboxylic acid such as succine and
phthalic anhydride.
2. Alcoholysis
-produce esters and carboxylic acids
-does not require catalyst but still require
heating
3. Ammonolysis
-ammonolysis of anhydrides with ammonia,
primary and secondary amines
-acetamide -
ammonium acetate
Amines and amides
Thursday, January 6, 2022
3:23 AM
Primary Amine
-nitrogen atom is bonded to one hydrocarbon
group and two hydrogen atoms
-RNH2
Secondary Amine
• In diamines, the final -e of the carbon chain
name is retained for ease of pronunciation.
Thus the base name for a four-carbon chain
bearing two amino groups is
butanediamine.
• Cyclic amines exist. Such compounds are
always either secondary or tertiary amines.
Cyclic amines are heterocyclic compounds.
Numerous cyclic amine compounds are
found in biochemical systems.
IUPAC Rules
-similar to alcohol
-alcohol: alkonols (-ol), amines: alkanamines (-
amine)
1. Select as the parent carbon chain the
longest chain in which the nitrogen atom is
attached.
2. Name the parent chain by changing the -e or
the alkane to -amine
3. Number the parent chain from the end • In amines where additional functional
nearest to the nitrogen atom. groups are present, the amine group is
4. The position of attachment of the nitrogen treated as a substituent. As a substituent, an
atom is indicated by a number in front of —NH2 group is called an amino group.
the parent chain name.
5. The identity and location of any
substituents are appended to the front of
the parent chain.
• Alkaloids
- is a nitrogen-containing organic compound
extracted from plant material.
• Codeine
- is less potent than morphine, having a
painkilling effect about one-sixth that of
morphine. Amides in which Methyl Groups are present
1. Methyl group attached to the carbon
• Heroin 2. Methyl group attached to the nitrogen
- is a semi-synthetic compound, the diacetyl
ester of morphine; it is produced from
morphine.
• Melatonin
-is a hormone that is synthesized by the
pineal gland and that regulates the sleep in
humans
-polyfunctional amide; amine and ether
groups are also present
• Acetaminophen
-derivative acetamide, which in 1992
replaced aspirin as the top-selling over-the-
counter pain reliever.
Nomenclature for Amides • Barbiturates
-based on name of the parent carboxylic acid:
-which are cyclic amide compounds, are a
1. -ic acid (common) or -oic acid (IUPAC) is
heavily used group of prescription drugs that
changed to -amide
cause relaxation (tranquilizers), sleep
(sedatives), and death (overdoses).
-derivatives of barbituric acid - cyclic amide
first synthesized from urea and malonic acid.