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ORGANIC COMPOUNDS WITH OXYGEN - Coggle Diagram
ORGANIC COMPOUNDS WITH OXYGEN
Alcohols
Chemical properties and preparation
Hydration
alkenes + water in acidic medium --> alcohol
Substitution
1° Haloalkanes + metal hydrides
Fermentation
glucose with enzymes --> ethanol + carbon dioxide
combustion of alcohols
alcohol + O2 --> CO2 + H2O + heat
ACIDITY
slightly acidic due to electronegativity of oxygen atoms
anion derived by the deprotonation (Na/K) - ALKOXIDE
Alcohols + Hydrogen halides
ROH + HX --> RX + H2O
dehydration of alcohols
with loss of -H and -OH from adjacent carbon atom
when heated with acid catalyst
alcohol with heat --> alkene + water
Oxidation of ethanol
by enzymes in the liver
aldehyde product impairs coordination
in the body
ethanol --> acetaldehyde --> acetic acid
Physical properties
R-OH structure
very polar
hydrogen bonds form easy
abnormally high boliling points
SOLUBILITY IN WATER
4 or less C atoms - water miscible
5 or more C atoms - not miscible
low molecular weight (5-6C atoms) - very polar
if there is more -OH groups - more soluble
higher molecular weight - less soluble
diols and triols more soluble
still polar
Nomenclature
replace the -e with -ol
number the parent chain
to minimize the number of carbon
with the -oh group
name the parent compound
Identify, name and number the substituents
Classification
by the number of alkyl groups attached to the carbinol
Secondary (2°)
Tertiary (3°)
primary (1°)
Monovalent
Bivalent
Trivalent
Important alcohols
Propan-2-ol - rubbing alcohol
Ethan-1,2-diol - antifreeze
Ethanol
depressant
alcohol in beverages
kills/disables more than any other drug
Methanol - fuel
Propan-1,2,3-triol - glycerol
Sorbitol or D-glucitol - sugar alcohol
Aldehydes and ketones
Nomenclature
Aldehydes
Determine the name of the groups bonded to parent chain
C of the aldehyde is counted as part of the root
Determine the parental chain by with the most C atoms
and aldehyde group at the and and change -e to -al
In a compound with keto group aldehyde is given priority,
keto in aldehyde is given suffix - oxo
common names
(2C) acetaldehyde
(3C) propionaldehyde
(1C) formaldehyde
(4C) butyraldehyde
Ketones
In the parent chain -e is changed to - on
Prefix a locant for carbonyl group with the lower number
Common names
alkyl groups attached to
the carbonyl group
in alphabetical order
and add word ketone
propanone - acetone or dimethyl-ketone
Physical properties
Aldehydes
only methanal is gas
they aren't solvents because they oxidize with oxygen from air
Ketones
weaker oxidants --> used as solvents
Common
Carbonyl group - C=O
strongly polar due to electronegative O
shorter-chained carbonyl compounds - completely soluble due to hydrogen bond between oxygen in carbonyl group and hydrogen in water
dipole-dipole forces between molecules
liquids except for methanal
Higher boiling point than alkenes
Incrase of Mf = growing Bp
Chemical properties and preparation
ketones
R2-CHOH --> R2-CO --> x
secondary alcohol --> ketone --> no reaction
Oxidation of secondary alcohols
Aldehydes
oxidation of primary alcohols
R-CH2OH --> R-COH --> R-COOH
primary alcohol --> aldehyde --> carboxylic acid
oxidation --> dehydrogenaton
reduction --> hydrogenation
with catalyst
Pt
aldehydes --> primary alcohols
ketones --> secondary alcohols
with metal hydrides
NaBH4
LiAlH4
Addition of alcohols
hemiacetals and hemiketals
unstable, difficult to isolate
cyclic if C=O g. and -OH g. are both 5-6 C atom compounds
glucose
aldose
aldohexose
pentahydroxyaldehyde
fructose
ketose
ketohexose
pentahydroxyketone
Carboxylic acids and esters
Esters
Nomenclature
Alkyl group from the alcohol in the first place
carbon chain from the acid with -ate ending
Physical properties
H in the carboxly group is replaced with an alkyl group
R(=O)OR'
Esters give flowers and fruits their pleasant smell
Chemical properties and preparation
Esterification
Carboxylic acid + alcohol in the presence of an acid catalyst = Esters + water
R(=O)OH + R-OH --> R(=O)OR + h20
Hydrolysis
Acid hydrolysis
Ester + water in the presence of acid catalyst --> carboxylic acid + alcohol
Base Hydrolysis
Ester + strong base --> salt of sarboxylic acid + alcohol
Aspirin
pain releaver
ester of salicylic acid and acetic acid
oil of wintergreen
for soothing sore muscles
salicylic acid and methanol
Carboxylic acids
Physical properties
Carbonyl + hydroxyl group = carboxyl group
CnH2nO2 --> C(=O)OH --> -COOH --> CO2H
Bronsted acids - proton donors
salts and anions - CARBOXYLATES
simplest: Alkanoic acids (R-COOH)
strongly polar - 2 polar groups
1-4 C atoms
very soluble
sharp smelling liquids
more C atoms
insoluble
solids
form h bonds with many water molecules
higher Bp than alcohol
Nomenclature
Classification
by the number of carboxyl groups
monocarboxylic a.
dicarboxylic a.
according to another functional g.
hydroxycarboxylic a. -OH
amino acids - NH3
Longest carbon chain, drop -e, add -oic acid
to the name of cycloalkane is added - carboxylic acid
a) aliphatic - dioic acid
b) cyclic - dicarboxylic acid
Common and trivial names
Methanoic - formic (ants)
Ethanoinc - acetic (vinegar, glacial)
propanoic - propionic (Na, K salts for food preservation)
butanoic - butyric (rancid butter, arnica oil, sweat)
2-hydroxypropanoic - lactic (sour milk, muscul fiber)
ethanedioic - oxalic (simplest diacid, in many foods, salts cause kidney stones (calcium oxalate)
nomencalture of carboxylates
cation name + name of acid. drop - ic acid, add -ate
Chemical properties and preparation
Reactions with metals (2RCOOH + 2M --> 2RCOOM + H2)
Reaction with alkalis (RCOOH+MOH--> RCOOM + H2O)
Oxidation of 1° alcohols or aldehydes
Reaction with bases
Neutralization
forms CARBOXLATES - water soluble
RCOOH + NaOH --> RCOO-Na+ + H2O
behave as typical acids in aq
form salts in reaction with metals and bases
condensation reactions with alcohols --> esters
reduced to 1° alcohols by using LiAl4
weak acids - small Ka
ionize in water --> carboxylate ions and hydronium ions
Oxidation numbers and redox reactions
Rules for determining oxidation number
Hydrogen's oxidation number is +1 , except for when bonded to metals as the hydride ion forming binary compounds. In LiH , NaH , and CaH2 , the oxidation number is −1 .
lkali metal oxidation numbers =+1 . Alkaline earth oxidation numbers =+2
Oxygen's oxidation number =−2 except when in hydrogen peroxide (H2O2), or a peroxide ion (O2−2) where it is −1
Monatomic ions have oxidation numbers equal to their charge. Li+=+1, Ba2+=+2
For free elements (uncombined state), each atom has an oxidation number of zero. H2 , Br2 , Na , Be , K , O2 , P4 , all have oxidation number of 0
Fluorine has an oxidation number of −1 in all of its compounds
Halogens ( Cl , Br , I ) have negative oxidation numbers when they form halide compounds. When combined with oxygen, they have positive numbers.
In a neutral atom or molecule, the sum of the oxidation numbers must be 0. In a polyatomic ion, the sum of he oxidation numbers of all the atoms in the ion must be equal to the charge on the ion.
Oxidation-reduction proccesses
RIG - gain of electrons
what is reduced is oxidant
what is oxidised is reducing agent
OIL - loss of electrons