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3) Why is Wurtz reaction not preferred for the preparation of alkanes containing
odd number of carbon atoms? Illustrate your answer by taking one example.
4) State Huckel’s rule. Draw the structure of Pyridine and Furan. Are these
aromatic?
5) Explain the mechanism involved in the chlorination of methane.
(i)
(ii)
(iii)
(iv)
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CHEMISTRY
1) Chain isomerism
2) Sodium
3) 2,3-dimethyl butane
4) Free radical mechanism
5) Staggered conformation
6) No
7) Due to the presence of pi bond in carbon to carbon double bond
8) sp2 hybridisation
9) CHCl = CHCl
10) Bromine
11) No. Free radical is not formed due to high bond dissociation energy of HCl
12) Dilute alkaline potassium permanganate solution.
13) Pd supported over barium sulphate or calcium carbonate poisoned with
quinoline or sulphur.
14) Ozonolysis
15) a. Bayer’s test
b. Bromination
16) As they are linear in nature.
17) Ethanal is formed.
18) 1,1-dichloroethane
19) Trans-2-butene
20) Benzene.
21) Planar
22) Due to delocalization of pi electron charge.
23) Anhydrous aluminium chloride
24) Ortho directing groups -- OH, NH2
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Meta directing groups --- CHO, NO2
25) Electrophilic substitution
26) Kekule
27) Nitronium ion
28) Liquefied natural gas
29) Methane.
1) The decomposition of higher alkane into a mixture of lower alkanes , alkenes etc
by the application of heat is called pyrolysis / cracking.
2) When unbranched alkanes are heated with anhydrous aluminium chloride and
hydrogen chloride isomeric branched alkanes are formed. This process is called
isomerization
3) X is Cis-but-2-ene ; Y is trans-but-2-ene
4)
5)
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7)
Due to the occurrence of both methyl groups on the same side of the C=C
bond, the combined effect of the two polar bonds makes cis-but-2-ene
much more polar than trans-but-2-ene.
8)
9)
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It is used to test for unsaturation.
11) Ketone
12) Markovnikov's rule states that, negative part of the addendum (adding molecule)
gets attached to that carbon atom which possesses lesser number of hydrogen
atoms.
13) Sodium salt of butanoic acid is required for the preparation of propane.
14) Alkyl halides on treatment with sodium metal in dry ether solution give
higher alkanes. This reaction is known as Wurtz reaction.
This reaction is used for the preparation of higher alkanes containing even number
of carbon atoms.
15) Sodium salts of carboxylic acids on heating with soda lime (mixture of sodium
hydroxide and calcium oxide) give alkanes containing one carbon atom less than
the carboxylic acid. This elimination of carbon dioxide from a carboxylic acid is
known as decarboxylation.
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16) Alkanes undergo free radical substitution. The examples of this category are
halogenation, nitration and sulphonation.
17) The spatial arrangements, which are obtained by free rotation around sigma
bonds, are called conformation or conformational isomers.
20)
22) Benzene is a planar molecule having delocalized electrons above and below the
plane of ring. Hence, it is electron-rich. As a result, it is highly attractive to electron
deficient species i.e., electrophiles. Therefore, it undergoes electrophilic substitution
reactions very easily. Nucleophiles are electron-rich. Hence, they are repelled by
benzene. Hence, benzene undergoes nucleophilic substitutions with difficulty.
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23) Any Lewis acid like anhydrous FeCl3, SnCl4, BF3 etc. can be used during the
ethylation of benzene.
24) Organic compounds containing only hydrogen and carbons are called
hydrocarbons.
25) The repulsive interaction between the electron clouds, which affects stability of a
conformation, is called torsional strain. Magnitude of torsional strain depends upon
the angle of rotation about C-C bond. This angle is called dihedral angle or torsional
angle. Of all the conformations of ethane, the staggered form has the least torsional
strain and the eclipsed form has the maximum torsional strain.
26)
a) Unusual stability of benzene.
b) According to Kekule, two ortho disubstituted products are possible. But in
practice only one ortho disubstituted product is known.
c) Heat of hydrogenation of benzene is 49.8 kcal/mole, whereas theoretical value of
heat of hydrogenation of benzene is 85.8 kcal/mole. It means resonance energy is
36 kcal/mole.
d) C - C bond length in benzene are equal, (although it contains 3 double bonds and
3 single bonds) and are 1.39 Å.
27)
H
H
H
H H
H H
H H H
H
H
Eclipsed Staggered
28)
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As the s–character increases, the electronegativity of carbon increases and the
electrons of C–H bond pair lie closer to the carbon atom. As a result, partial
positive charge of H–atom increases and H+ ions are set free. The s–character
increases in the order: sp3 < sp2 < sp. Hence, the decreasing order of acidic
behaviour is Ethyne > Benzene > Hexane.
This ozonide is formed as an addition of ozone to ‘A’. The desired structure of ‘A’ can be
obtained by the removal of ozone from the ozonide. Hence, the structural formula of ‘A’
is:
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where an electron-rich species is attacked by a nitronium ion (NO2+). Now, CH3–
group is electron donating and NO2– is electron withdrawing. Therefore, toluene will
have the maximum electron density among the three compounds followed by
benzene. On the other hand, m– dinitrobenzene will have the least electron density.
Hence, it will undergo nitration with difficulty.
3) Wurtz reaction cannot be used for the preparation of unsymmetrical alkanes because if
two dissimilar alkyl halides are taken as the reactants, then a mixture of alkanes is
obtained as the products. Since the reaction involves free radical species, a side reaction
also occurs to produce an alkene. For example, the reaction of bromomethane and
iodoethane gives a mixture of alkanes.
The boiling points of alkanes (obtained in the mixture) are very close. Hence, it becomes
difficult to separate them.
4) Huckel’s rule states that, compounds that have (4n + 2) -electrons, are said to
be Aromatic compounds, where n = 1,2,3,4….etc.
Pyridine is aromatic because it folllows Huckel's rule and has 6 pi electrons where n=1.
Furan is also aromatic compound because one of the lone pair of electrons at the oxygen
delocalise towards benzene ring and then it follows Huckel's rule where n=1.
5) Chlorination of methane proceeds via a free radical chain mechanism. The whole
reaction takes place in the given three steps.
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Step 1: Initiation:
Step 2: Propagation:
In the second step, chlorine free radicals attack methane molecules and break down the
C–H bond to generate methyl radicals as:
These methyl radicals react with other chlorine free radicals to form methyl chloride
along with the liberation of a chlorine free radical.
Hence, methyl free radicals and chlorine free radicals set up a chain reaction. While HCl
and CH3Cl are the major products formed, other higher halogenated compounds are also
formed as:
Step 3: Termination:
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6) (i)
For the given compound, the number of ʌ-electrons is 6.By Huckel’s rule,
4n + 2 = 6; 4n = 4; n = 1
(ii)
By Huckel’s rule, 4n + 2 = 4; 4n = 2 ;
(iii)
By Huckel’s rule, 4n + 2 = 8; 4n = 6;
7) (i) Pen-1-ene-3-yne
(ii) Buta-1,3-diene
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(iv) 2-Methyl phenol
8)
This reaction follows Markovnikov’s rule where the negative part of the addendum is
attached to the carbon atom having a lesser number of hydrogen atoms.
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Secondary free radicals are more stable than primary radicals. Hence, the former
predominates since it forms at a faster rate. Thus, 1 – bromopropane is obtained as the
major product.
In the presence of peroxide, Br free radical acts as an electrophile. Hence, two different
products are obtained on addition of HBr to propene in the absence and presence of
peroxide.
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(ii) Benzene to acetophenone
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11) The structure of benzene molecule is best described in terms of molecular orbital
treatment theory. According to this theory, all the C-atoms in benzene are sp2-
hybridized. Two sp2-hybrid orbitals of each C-atom overlap with two sp2-hybrid orbital
of two other C-atoms to form sigma bonds. In this way there are six sigma bonds are
formed between six C-atoms which are 120o apart. Remaining six sp2-orbital of six C-
atoms overlap with 1s orbital of six H-atoms individually to form six sigma bonds. Since
sigma bond results from the overlap of above said planar orbital, all H and C atoms are in
the same plane and their generate a hexagonal ring of C-atoms
Each C-atom in benzene also has an unhybrid 2pz-orbital containing one electron. These
2pz-orbital are perpendicular to the plane of sigma bonds.
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25
Actually these 2pz-orbital produce a pi-molecular orbital containing six electrons. One
half of this pi- molecular orbital lies above the plane of hexagonal ring and remaining
half below the ring like a sandwich.
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