CH-6 Chemistry Qa
CH-6 Chemistry Qa
CH-6 Chemistry Qa
10.1. Name the following halides according to the IUPAC system and classify
them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl, or aryl halides:
(i)(CH3)2CHCH(Cl)CH3
(ii) CH3CH2CH(CH3)CH(C2H5)CI
(iii) CH3CH2C(CH3)2CH2I
(iv)(CH3)3CCH2CH(Br)C6H5
(v)CH3CH(CH3)CH(Br)CH3
(vi)CH3C(C2H5)2CH2Br
(vii)CH3C(Cl)(C2H5)CH2CH3
(viii)CH3CH=C(CI)CH2CH(CH3)2
(ix)CH3CH=CHC(Br)(CH3)2
(x)P-CIC6H4CH2CH(CH3)2
(xi)m-ClCH2C6H4CH2C(CH3)3
(xii)o-Br -C6H4CH (CH3)CH2CH3
Ans: (i) 2-Chloro-3methylbutane, 2° alkyl halide
(ii) 3-Chloro-4methyl hexane, 2° alkyl halide
(iii) 1 -Iodo-2,2-dimethylbutane, 1 ° alkyl halide
(iv) l-Bromo-3, 3-dimethyl -1-phenylbutane, 2° benzylic halide
(v) 2-Bromo-3-methylbutane, 2° alkyl halide
(vi) 1-Bromo-2-ethyI-2-methylbutane, 1° alkyl halide
(vii)3-Chloro-3-methylpentane, 3° alkyl halide
(viii) 3-Chloro-5-methylhex-2-ene, vinylic halide
(ix)4-Bromo-4-methylpent-2-ene, allylic halide
(x)1-Chloro-4-(2-methylpropyl) benzene, aryl halide
(xi)1-Chloromethyl-3- (2,2-dimethylpropyl) benzene, 1 ° benzylic halide.
(xii)1-Bromo-2-(l-methylpropyl) benzene,aryl halide.
10.4. Which one of the following has the highest dipole moment?
(i)CH3CI2 (ii) CHCl3 (iii) CCI4
Ans: The three dimensional structures of the three compounds along with the direction
of dipole moment in each of their bonds are given below:
CCl4 being symmetrical has zero dipole moment. In CHCl 3, the resultant of two C – Cl
dipole moments is opposed by the resultant of C – H and C – Cl bonds. Since the dipole
moment of latter resultant is expected to be smaller than the former, CHCl 3 has a finite
dipole (1.03 D) moment.
In CH2CI2, the resultant of two C – Cl dipole moments is reinforced by resultant of two C
– H dipoles, therefore, CH2CI2 (1 .62 D) has a dipole moment higher than that of CHCl 3.
Thus, CH2CI2 has highest dipole moment.
10.5. A hydrocarbon C5H10 does not react with chlorine in dark but gives a single
monochloro compound C5H9CI in bright sunlight. Identify the hydrocarbon.
Ans: The hydrocarbon with molecular formula C5H, 0 can either a cycloalkane or an
alkene.
Since the compound does not react with Cl2 in the dark, therefore it cannot be an alkene
but must be a cycloalkane. Since the cycloalkane reacts with Cl2 in the presence of
bright sunlight to give a single monochloro compound, C 5H9Cl, therefore, all the ten
hydrogen atoms of the cycloalkanes must be equivalent. Thus, the cycloalkane is
cyclopentane.
It can attack through carbon to form cyanide and through N to form is O cyanide.
10.9. Which compound in each of the following-pairs . will react faster in SN2
reaction with -OH? (i)CH3Br or CH3I
(ii)(CH3)3CCl or CH3Cl
Ans: (i)Since I– ion is a better leaving group than Br- ion, therefore, CH3I reacts faster
CH3Br in SN2 reaction with OH– ion.
(ii)On steric grounds, 1° alkyl halides are more reactive than tert-alkyl halides in SN2
reactions. Therefore, CH3CI will react at a faster rate than (CH3)3CCl in a SN2 reaction
with OH– ion.
10.10. Predict all the alkenes that would be formed by dehydrohalogenation of the
following halides with sodium ethoxide in ethanol and identify the major alkene:
(I) 1-Bromo-l-methylcyclohexane
(ii) 2-Chloro-2-methylbutane.
(iii) 2,2,3-Trimethyl-3-bromopentane.
Ans:
(ii) Alkyl halides are polar molecules, therefore, their molecules are held together by
dipole-dipole attraction. The molecules of H2O are hold together by H-bonds. Since the
new forces of attraction between water and alkyl halide molecules are weaker than the
forces of attraction already existing between alkyl halide – alkyl halide molecules and
water-water molecules, thefefore, alkyl halides are immiscible (not soluble) in water.
Alkyl halide are neither able to form H- bonds with water nor are able to break the H-
bounding network of water.
(iii)Grignard reagents are very reactive. They react with moisture present in the
apparatus to form alkanes
10.13. Give the uses of freon 12, DDT, carbon tetrachloride, and iodoform.
Ans: Iodoform: It was earlier used as an antiseptic but the antiseptic properties are due
to the liberation of free iodine and not due to iodoform itself. Due to its objectionable
smell, it has been replaced by other formulations containing iodine.
Carbon tetrachloride:
Uses:
(i)As an industrial solvent for oil, fats, resins etc.and also in dry cleaning.
(ii)CCl4 vapours are highly non-inflammable, thus CCl4 is used as a fire extinguisher
under the name pyrene.
(iii)Used in the manufacture of refrigerants and propellants for aerosol cans.
Freons: Freon-12 (CCl2F2) is most common freons in industrial use.
Uses: For aerosol propellants, refrigeration, and air conditioning purposes.
DDT (p -p’ – Dichloro diphenyl – trichloro ethane):
(i)The use of DDT increased enormously on a worldwide basis after World War II,
primarily because of its effectiveness against the mosquitoes that spreads malaria and
other insects which damages crops.
(ii) However, problems related to extensive use of DDT began to appear in the late 1940
s. Many species of insects developed resistance to DDT, it was also discovered to have
a high toxicity towards fishes. DDT is not metabolised very rapidly by animals, instead, it
is deposited and stored in the fatty tissues. If the ingestion continues at a steady rate,
DDT builds up within the animal’s overtime.
10.14. Write the structure of the major organic product in each of the following
reactions:
Ans:
Thus, CN– ion is an ambident nucleophile. Therefore, it can attack the “carbon atom of
C-Br bond in n-BuBr either through C or N. Since C – C bond is stronger than C – N
bond, therefore, attack occurs through C to form n-butyl cyanide.
10.16. Arrange the compounds of each set in order of reactivity towards SN2
displacement:
(i) 2-Bromo-2-methyibutane, 1-Bromopentane, 2-Bromopentane.
(ii) l-Bromo-3-methyIbutane, 2-Bromo-2-methylbutane, 3-Bromo-2-methylbutane.
(iii) 1-Bromobutane, l-Bromo-2,2-dimethylpropane, l-Bromo-2-methylbutane, l-
Bromo-3-methyl butane.
Ans: The SN2 reactions reactivity depends upon steric hindrance. More the steric
hindrance slower the reaction.Thus the order of reactivity will be 1°> 2° >3°
Since in case of 1° alkyl halides steric hindrance increases in the order) n-alkyl halides,
alkyl halides with a substituent at any position other than the β-position, one substituent
at the β-position, two substituents at the β-position, therefore, the reactivity decreases in
the same order. Thus, the reactivity of the given alkyl bromides decreases in the order:
1-Bromobutane > l-Bromo-3-methylbutane > l-Bromo-2-methyjbutane> 1-Bromo-2,2-
dimethyl propane.
10.18. p-dichlorobenzene has higher m.p. and lesser solubility than those of o-
and m-isomers. Discuss. (C.B.S.E. Delhi 2013)
Ans: The three isomers are position isomers which differ in the relative positions of the
chlorine atoms in the ring :
10.21. Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give
compound (b) Compound (b) is reacted, with HBr to give (c) which is an isomer of
(a). When (a) is reacted with sodium metal it give compound (d), C8H18 which is
different from the compound formed when n-butyl bromide is reacted with
sodium. Give the structural formula of (a) and write the equations for all the
reactions.
Ans: (i) There are two primary alkyl halides having the molecular formula, C4H9Br.
(ii) Since compound (a) when reacted with Na metal gave a compound (d) with
molecular formula C8H18 which was different from die compound obtained when n-butyl
bromide was reacted with Na metal, therefore, (a) must be isobutyl bromide and
compound (d) must be 2,3-dimethylhexane.
(iii) If compound (a) is isobutyl bromide, than the compound (b) which it gives on
treatment with alcoholic KOH must be 2-methyl-1-propane.
(iv) The compound (b) on treatment with HBr gives compound (c) in accordance with
Markownikoff rule. Therefore, compound (c) is tert-butyl bromide which is an isomer of
compound (a) ,i.e., isobutyl ‘ bromide.
Thus
(a)is isobutyl bromide,
(b)is 2-methyl-1 -propane,
(c)is tert-butylbromide, and
(d)is 2,5-dimethylhexane.