ORGANIC CHEMISTRY Markovnikoff's Rule, "The halogen attaches to the
Friedrich Wohler – synthesized urea in lab. From the carbon that is more alkyl substituted thus producing a
inorganic compound, ammonium cyanate. Urea is a higher order alkyl halide."
component of urine Preparation of Alkynes
Structural Theory 1. Reaction of Sodium Acetylide with Alkyl Halides
- Atoms in. an organic compound have fixed (Alkylation)
number of bonds. This combining ability is 2. Dehydrohalogenation of Vicinal Dihalides/ alkyl
termed as valence. halides
- Carbon can form bonds with another carbon 3. Dehalogenation of Tetrrahalides
atom accounting for a high percentage of Source and Properties of Benzene
carbon in most organic compounds. This ability • obtained from catalytic dehydrogenation of
of carbon is called ·catenation. cyclohexane and from coal tars
Ionic bond – gaining or losing electrons, Atoms with • stabilized by de localization of 1t electrons
high ionization energy tend to lose electrons easily • all C-H bonds are equivalent
while atoms with low electron affinity tend to gain • does not decolorize KMn04
electrons easily. • H2 does not add even in the presence of a metal
Covalent bond – sharing of electrons with another catalyst
atom, Atoms forming covalent bonds share electrons to • undergoes substitution reaction
acquire the configuration of the noble gases (octet rule). Physical Properties of Alcohols and Ethers
Hydrogen acquires the electron configuration of the 1. Boiling Point – alcohols have higher boiling pts
noble gas helium. compared to ethers due to hydrogen bonding
Resonance Theory - A molecule or an ion represented in 2. Solubility in water – solubility decreases as
two or more Lewis structures that differ only in the chain length increases
positions of electrons ·exhibit the property of Physical Properties of Aldehydes and Ketones
resonance. These structures are called resonating 1. Boiling Point -intermediate between alkanes
structures or resonating contributors. and alcohols of the same molecular weight
Alkyl Halides 2. Solubility in Water - due to high polarity,
Density – greater than that of water aldehydes and ketones are soluble in water
Boiling point – will be larger than the hydrocarbon Physical Properties of Phenols
Water Solubility – insoluble in water - Exist at liquid at room temp.
ALKANES – physical state at room temp. - Low melting and boiling pts
No. of carbons 1 – 4 (gases), 5-17 (liquids), 18+ (solids) - Slight solubility in water, in strong basic medium
Solubility – insoluble in water due to non-polar, soluble phenols are converted into their salts or
in benzene, chloroform and CCl3 phenoxides
Boiling point – increases as carbon increases, decreases Physical Properties of Carboxylic Acids
due to branching - Unpleasant odors
Preparation of Alkane - Higher boiling pts compared to alcohols
1. Grignard synthesis using alkyl halide (hydrolysis - Exhibit solubility in water, decreases as the
of Grignard reagent) number of carbon increases
2. Hydrogenation of alkene (addition rxn) Physical Properties Carboxylate Salts
3. Reduction of alkyl halide - Very high melting points
4. Wurtz synthesis (coupling rxn) - Ready soluble in water
Preparation of Alkene Physical Properties of Esters
1. Dehydration of Alcohol - Pleasant odor
2. Dehydrogenation of Alkyl halides - Boiling and melting point similar to aldehydes
3. Debromination of dibromides and ketones
4. Dehalogenation of vicinal dihalides (vic- - Lesser number of carbon are soluble in water
dihalides) - Polarity decreases as the number of carbon
increases
o Oxidation of isopropyl alcohol with KMn04 will
Physical Properties of Amides yield acetone
- Derivatives of carboxylic acids o In Williamson synthesis of methyl isopropyl ether,
- High boiling points the alcohol used is isopropyl alcohol
- Small amides are polar and therefore soluble in o Acid-catalyzed ring opening of an epoxide will
water result in the formation of a/an dihydric alcohol
- Primary and secondary amides are soluble, o Which ofthe following tests will distinguish !-
tertiary are less soluble propanol from 2-propanol? Lucas Test
Physical Properties of Amines o Ozonolysis of alkenes yield an aldehyde
- Aromatic amines are very toxic, pungent, o A tertiary alcohol is produced using Grignard
unpleasant and fishy smell Reagent using a/an ketone
- Polar compounds, same as amides o Carbonyl compounds can be obtained by
- Primary have higher boiling pt than secondary, reduction using the following except amide
tertiary have lower boiling and melting point o Addition of hydrazine to carbonyl compounds
REVIEW QUESTIONS AND PROBLEMS produces a/an hydrazone
o Sigma – bond formed in the head-on overlap of o Reduction of alkyl phenyl ketones to aromatic
two orbitals hydrocarbons done by Wolf-Kishner Reduction
o When ethyl bromide is treated with sodium in dry uses NH2NH2, KOH
ether, the product is a. propane b. butane c. o Acid anhydrides upon hydrolysis yield a. esters b.
methylpropane d. ethane (ans b) amides c. carboxylic acid d. acyl halide (Ans. C)
o Halogenation - during halogenation, a free radical o Hexanedioic acid is also known as a. malonic acid
of the halogen is formed in the presence of light b. succinic acid c. glutaric acid d. adipic acid (ans.
or heat D)
o How many possible monochlorinated product is o Reaction of alcohol and a carboxylic acid is known
expected from the chlorination of propane? – 1 as esterification
o Among the following alcohols, methylpropene o Addition of an alcohol to acyl halides produces a.
can be obtained from 2-methyl-2-propanol carboxylic acid c. carboxamide · b. ester d. none
o The acid-catalyzed addition of. water to 1-butene of these (ans b)
will form 2 butanol o Addition of water to acid anhydrides produces a.
o Starting with 2-methyl-2-butene, which of the carboxylic acid b. ester c. amide · d. none of these
following processes must be used to produce a (ans. A)
secondary alcohol? Hydroboration-oxidation o Addition of ammonia to acid anhydrides produces
o Hydrogenation of alkynes in the presence of a a. carboxylic acid b. ester c. amide d. none of
poisoned palladium catalyst produces alkenes these (ans. C)
o Addition of HBr to alkynes results in the o When an ethyl acetate is reduced by LiAIH4 the
formation of germinal dihalide. product is acetaldehyde
o When 2-butyne undergoes ozonolysis, the main o Cyclic esters are knows as lactones
product is acetic acid o The scent of a banana is due to the ester i-pentyl
o In hydration of alkynes, the enol formed is found acetate
to transform into a ketone. This form of Common Preparation/Sources
isomerism is known a keto-enol tautomerism ALCOHOL
o Vinylbenzene is also known as styrene a. Industrial Scale - Fermentation of Carbohydrates
o Chlorination of aniline will produce dominantly 4- b. Laboratory Scale
chloroaniline a. Hydration of Alkenes (acid-catalyzed)
o Which of the following carbonyl compounds b. Reduction of Carbonyl Compounds
produce a secondary alcohol with LiAlH4? Ketone > Aldehydes and Ketones can be reduced to alcohols
o Addition of methyl magnesium bromide to using reducing agents like sodium borohydride (NaBH₄)
acetaldehyde produces 2-propanol or lithium aluminum hydride (LiAlH₄).- ketone yields 2o
alcohol while aldehyde yields 1o alcohol
Example: CH3CHO+NaBH4→CH3CH2OH
➢Carboxylic Acid
➢Ester
c. Hydroboration-Oxidation - addition of boron and
hydrogen across double bond and subsequent oxidation
yields an alcohol
d. Using Grignard Reagents and Organolithium
Compounds- reaction between an alkyl or aryl
magnesium halide (Grignard Reagents) and carbonyl
compound (aldehyde or ketone)
> Ketone yields 3o alcohol, Aldehyde yields 2 alcohol,
Methanal yields 1o alcohol
e. Oxidation of Alkenes- alkenes can be oxidized to form
diols (alcohol with two hydroxyl groups) and subsequent
treatment with acid
