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1. Name the following halides according to IUPAC system and classify them
as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
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a. (CH3)2CHCH(Cl)CH3
b. CH3CH2CH(CH3)CH(C2H5)Cl
c. CH3CH2C(CH3)2CH2I
d. (CH3)3CCH2CH(Br)C6H5.
•
Solution:
a. 2-chloro-3-methyl butane (sec)
b.3-chloro-4-methyl-hexane[sec]
c. 1- ido-2, 2-dimethyl butane
d. 1-bromo –3,3-dimethyl-1-phenyl-butane[sec,,benzylic]
2. Name the following halides according to IUPAC system and classify
them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl
halides:
a. CH3CH(CH3)CH(Br)CH3
b. CH3C(C2H5)2CH2Br
c. CH3C(Cl)(C2H5)CH2CH3
d. CH3CH=C(Cl)CH2CH(CH3)2.
•
Solution:
b. 1-bromo-2-ethyl-2-methyl-butane[pri]
in
a. 2-bromo-3-methyl butane (sec)
c. 3-chloro-3-methyl-pentane[ter]
d. 3-chloro-5-methyl-hex-2-ene[vinylic]
3. Name the following halides according to IUPAC system and classify
them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl
halides:
1
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a. CH3CH=CHC(Br)(CH3)2
b. p-ClC6H4CH2CH(CH3)2
c. m-ClCH2C6H4CH2C(CH3)3
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d. o-Br-C6H4CH(CH3)CH2CH3.
•
Solution:
a. 4-bromo-4-methyl- pent-2-ene [allylic]
b. 1-chloro-4-(2-methyl propyl ) benzene(aryl) (sec)
c. 1-chloro methyl-3-(2,2-dimethyl propyl)benzene [benzylic])
d. 1-bromo-2(1-methyl propyl) benzene.[aryl]
4. Give the IUPAC names of the following compounds:
i. CH3CH(Cl)CH(Br)CH3
ii. CHF2CBrClF
iii. ClCH2C ßCCH2Br.
•
Solution:
i. 2-bromo-3-chloro-butane
ii. 1-bromo,1-chloro,1,2,2-tri fluoro ethane
iii. 1-bromo-4-chloro-but-2-yne
5. Give the IUPAC names of the following compounds:
i. (CCl3)3CCl
iii. (CH3)3CCH=ClC6H4I-p.
•
in
ii. CH3C(p-ClC6H4)2CH(Br)CH3
Solution:
i 2-(trichloro methyl)-1,1,1,2,3,3,3-hepta chloro propane.
ii 2-bromo—3,3-bis( p- chloro phenyl) butane
iii 1-chloro-1-(4-iodo phenyl) -3,3-dimethyl-but-1-ene.
2
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6. Write the structures of the following organic halogen compounds.
i. 2-Chloro-3-methylpentane
ii. p-Bromochlorobenzene
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iii. 1-Chloro-4-ethylcyclohexane
iv. 2-(2-Chlorophenyl)-1-iodooctane.
•
Solution:
i.
ii.
iii.
7. Write the structures of the following organic halogen compounds.
i. Perfluorobenzene
iii. 1-Bromo-4-sec-butyl-2-methylbenzene
in
ii. 4-tert-Butyl-3-iodoheptane
vi. 1,4-Dibromobut-2-ene.
•
Solution:
3
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iv.
.
8. Which one of the following has the highest dipole moment?
i. CH2Cl2
ii. CHCl3
iii. CCl4.
•
Solution:
i. CH2Cl2
9. A hydrocarbon C5H10 does not react with chlorine in dark but gives a
single monochloro compound C5H9Cl in bright sunlight. Identify the
hydrocarbon.
•
Solution:
The higher alkanes do not react in dark, but in ultraviolet light or higher temperature
gives monochloro derivative as main product. Pentene or chlorination in presence of
sunlight gives monohalogen derivative.
•
in
10. Write the isomers of the compound having formula C4H9Br.
Solution:
a.
- 1-bromobutane
b.
- 1-bromo-2-methyl propane
4
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c.
- 2-bromo- 2-methyl propane
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d.
- 2-bromobutane.
11. Write the equations for the preparation of 1-iodobutane from
(i) 1-butanol (ii) 1-chlorobutane (iii) but-1-ene.
•
Solution:
(i)
(ii)
(iii)
.
12. What are ambident nucleophiles? Explain with an example.
•
Examples are C ≡ N (reagent KCN, AgCN) etc
Nitrite O = N – O- (KNO2, AgNO2).
in
Solution:
The nucleophiles with two nucleophilic centers are called ambident nucleophile. They
can react through either of these centers. Depending on the reagent and the reaction
conditions; the reaction may take place predominantly at one of these centers.
13. 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.
5
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•
Solution:
Methyl iodide is more reactive than methyl bromide as iodide is a better leaving group.
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14. 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-1-methylcyclohexane
ii. 2-Chloro-2-methylbutane
iii. 2,2,3-Trimethyl-3-bromopentane.
•
Solution:
i. 1 - methyl cyclohexene
ii. 2 - methyl but-2-ene
iii. 3,4,4-trimethyl-pent-2-ene
15. How will you bring about the following conversions?
i. Ethanol to but-1-yne
ii. Ethene to bromoethane
iii. Propene to 1-nitropropane
iv. Toluene to benzyl alcohol
v. Propene to propyne.
•
Solution:
in
ii.
iii.
6
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.
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vi.
v.
16. How will you bring about the following conversions?
i. Ethanol to ethyl fluoride
ii. Bromomethane to propanone
iii. But-1-ene to but-2-ene
iv. 1-Chlorobutane to n-octane
v. Benzene to biphenyl.
•
Solution:
i.
ii.
in
iii.
iv.
7
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v.
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17. Explain why
i. The dipole moment of chlorobenzene is lower than that of cyclohexyl
chloride?
ii. Alkyl halides, though polar, are immiscible with water?
iii. Grignard reagents should be prepared under anhydrous conditions?
•
Solution:
i. The low dipolemoment of chlorobenzene is due to resonance phenomenon. The
polarity and hence dipole moment is due to resonance effect as a result the
transmission of π - electron in conjugate π - bonds is very little.
Where as there is no resonance in cyclohexyl chloride, but the polarity and hence
dipolemoment is due to induction effect which is more.
ii. All the halogen derivatives of hydrocarbon are polar in nature but they are insoluble
in water, because they are unable to form hydrogen bond with water to break the
hydrogen bond already present in water. They are soluble in organic solvents.
iii. Grignard reagent should be prepared under anhydrous conditions, because it is
very reactive. It reacts very quickly with any source of proton to give hydrocarbon. It
reacts with water very quickly. Therefore, it is necessary to avoid moisture from the
Grignard reagents.
18. Give the uses of Freon 12, DDT, carbon tetrachloride and iodoform.
•
b) It is also used as a propellant in aerosols and foams to spray out deodorants,
cleaners, hair sprays, shaving creams and
in
Solution:
Freon12
a) It is used as a refrigerant (cooling agent) in refrigerators and air conditioners,
c) It is also used as insecticides.
Carbon tetrachloride
a) It is used as a solvent for oils, fats and waxes.
b) It is used as a fire extinguisher under the name pyrene.
8
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c) It is used as dry cleaning.
Iodoform
a) It is used as antiseptic and this nature is due to iodine that it liberates.
b) It is used in the manufacture of pharmaceuticals.
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19. Write the structure of the major organic product in each of the
following reactions:
i.
ii.
iii.
iv.
•
Solution:
i.
ii.
iii.
20. Write the structure of the major organic product in each of the
following reactions:
in
iv.
i.
ii.
iii.
9
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iv.
•
Solution:
i.
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ii.
iii.
iv.
21. Write the mechanism of the following reaction:
nBuBr + KCN
EtOH – H2O
•
€nBuCN
Solution:
€n-BuBr is a primary halide
Undergoes nucleophilic substitution by SN2 mechanism
CN- appraoaches the carbon atom from the side opposite at the halogen atom and
forms a covalent bond and at the same time Br leaves as BrThe transition state is
in
The nucleophiles, Nu- approaches the carbon atom on the side opposite from the
halogen and forms new covalent bond with the carbon of the group –C-X as the
displaced base, X-, leaves Nu- + R-X slow Nu…….R…….X fast
10
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Nu—R + XRX + KCN transition state
RC = N + KX
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This is because KCN is an ionic compound, K+ [CN-], Since carbon carrying a lone pair
of electrons is more reactive than nitrogen carrying a lone pair, the transition state is
formed by the carbon of the cyanide ion forming band with the carbon of the –C-X.
22. Arrange the compounds of each set in order of reactivity towards
SN2 displacement:
i. 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
ii. 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 3-Bromo-2methylbutane
iii. 1- Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2methylbutane, 1-Bromo-3-methylbutane.
•
Solution:
i. 1-Bromopentane, 2-Bromopentane, 2-Bromo-2-methylbutane,[ in decreasing order]
ii .1-bromo-3-methyl butane, 2-bromo- 3 – methyl butane,2-bromo-2-methyl-butane
iii. 1- Bromobutane, 1-Bromo-3-methyl-butane,1-bromo-2-methyl-butane,1-bromo2,2 dimethyl propane.
23. Out of C6H5CH2Cl and C6H5 CHClC6H5 , which is more easily hydrolysed
by aqueous KOH.
•
Solution:
C6H5CH2Cl is a primary halide and undergoes hydrolysis bySN2 mechanism.
in
C6H5CHClC6H5 undergoes hydrolysis by SN1 or SN2 mechanism. Though the
carbocation in this case is more stable, there is steric hindrance and hence
SN2 mechanism is followed and the first one is more readily hydrolysed.
24. p-Dichlorobenzene has higher m.p. and solubility than those of o- and
m-isomers. Discuss.
•
Solution:
The melting of p-isomer is quite higher than ortho and meta isomer. This is due to the
fact that it has symmetrical strcture and therefore its molecules can be easily packed
closely in crystal lattice. As a result, intermolecular forces of attraction are stronger
and therefore greater energy is required to break its lattice and it melts at higher
temperature.
11
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25. The treatment of alkyl chlorides with aqueous KOH leads to the
formation of alcohols but in the presence of alcoholic KOH, alkenes are major
products. Explain.
•
Solution:
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Aqueous KOH contains only OH- ions, which acts as nucleophiles and these bring about
hydrolysis of alkyl chlorides to the corresponding alchohol.
In the case of alcoholic KOH, the ethoxide ion present is a strong base and removes
HCl.
26. Primary alkyl halide C4H9 Br (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 gives 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.
•
Solution:
According to the problem when alkyl bromide (A) was treated with sodium, it gave a
compound which is not a straight chain hydrocarbon. Therefore (A) cannot be butyl
bromide. It may be isobutyl bromide. The complete reactions are
in
27. Write structures of the following compounds:
i. 2-Chloro-3-methylpentane
ii. 1-Chloro-4-ethylcyclohexane
iii. 4-tert. Butyl-3-iodoheptane
12
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iv. 1,4-Dibromobut-2-ene
v. 1-Bromo-4-sec. butyl-2-methylbenzene.
•
Solution:
i.
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ii.
iii.
iv.
v.
28. Why is sulphuric acid not used during the reaction of alcohols with KI?
•
Solution:
H2SO4 cannot be used along with KI in the conversion of an alcohol to an alkyl iodide
as it converts KI to corresponding HI and then oxidises it to I2.
29. Write structures of different dihalogen derivatives of propane.
•
Solution:
i. ClCH2CH2CH2Cl
ii. ClCH2CHClCH3
iv. CH3CCl2CH3.
in
iii. Cl2CH2CH2CH3
30. Among the isomeric alkanes of molecular formula C5H12, identify the
one that on photochemical chlorination yields
i. A single monochloride.
ii. Three isomeric monochlorides.
13
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iii. Four isomeric monochlorides.
•
Solution:
i. All the hydrogen atoms are equivalent and replacement of any hydrogen will give
the same product.
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ii. The equivalent hydrogens are grouped as a, b and c. The replacement of equivalent
hydrogens will give the same product.
iii. Similarly the equivalent hydrogens are grouped as a, b, c and d. Thus, four
isomeric products are possible.
31. Draw the structures of major monohalo products in each of the following
reactions:
i.
ii.
•
Solution:
in
iii.
i.
4
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ii.
.
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iii.
32. Arrange each set of compounds in order of increasing boiling points.
i. Bromomethane, Bromoform, Chloromethane, Dibromomethane.
ii. 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.
•
Solution:
i. Chloromethane, Bromomethane, Dibromomethane, Bromoform. Boiling point
increases with increase in molecular mass.
ii. Isopropyl chloride, 1-Chloropropane, 1-Chlorobutane. Isopropyl chloride being
branched has lower b.p. than 1-Chloropropane.
33. In the following pairs of halogen compounds, which compound
undergoes faster SN1 reaction?
•
Solution:
in
Tertiary halide reacts faster than secondary halide because of the greater stability of
tert-carbocation.
34. Write the structure of the major organic product in each of the
following reactions
i.
1
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ii.
iii.
.
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iv.
v.
vi.
vii.
viii.
•
Solution:
i.
ii.
iii.
in
iv.
v.
vi.
16
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vii.
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viii.
35. How can the following conversions be carried out?
i. Propene to propan-1-ol
ii. Ethanol to but-1-yne
iii.1-Bromopropane to 2-bromopropane
iv.Toluene to benzyl alcohol
v. Benzene to 4-bromonitrobenzene
vi. Benzyl alcohol to 2-phenylethanoic acid
vii. Ethanol to propanenitrile
viii. Aniline to chlorobenzene
ix. 2-chlorobutane to 3, 4-dimethylhexane
x. 2-methyl-1-propene to 2-chloro-2-methylpropane
xi. Ethyl chloride to propanoic acid
xiii. 2-Chloropropane to 1-propanol
in
xii. But-1-ene to n-butyliodide
xiv. Isopropyl alcohol to iodoform
xv. Chlorobenzene to p - nitrophenol
xvi. 2-Bromopropane to 1-bromopropane
xvii. Chloroethane to butane
17
CONTACT FOR MATHEMATICS GROUP/HOME COACHING FOR CLASS 11TH 12TH BBA,BCA,
DIPLOMA CPT CAT SSC AND OTHER EXAMS Also home tutors for other subjects in south and west delhi
EMAIL:17 [email protected] web site www.mathematic.in
MATHEMATIC CENTER D96 MUNIRKA VILLAGE NEW DELHI 110067 & VIKAS PURI NEW DELHI
CONTACT FOR COACHING MATHEMATICS FOR 11TH 12TH NDA DIPLOMA SSC CAT SAT CPT
CONTACT FOR ADMISSION GUIDANCE B.TECH BBA BCA, MCA MBA DIPLOMA AND OTHER COURSES 09810144315
xviii. Benzene to diphenyl
xix. tert - Butyl bromide to isobutyl bromide
xx. Aniline to phenylisocyanide
•
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ii.
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vi.
in
vii.
Viii.
18
CONTACT FOR MATHEMATICS GROUP/HOME COACHING FOR CLASS 11TH 12TH BBA,BCA,
DIPLOMA CPT CAT SSC AND OTHER EXAMS Also home tutors for other subjects in south and west delhi
EMAIL:18 [email protected] web site www.mathematic.in
MATHEMATIC CENTER D96 MUNIRKA VILLAGE NEW DELHI 110067 & VIKAS PURI NEW DELHI
CONTACT FOR COACHING MATHEMATICS FOR 11TH 12TH NDA DIPLOMA SSC CAT SAT CPT
CONTACT FOR ADMISSION GUIDANCE B.TECH BBA BCA, MCA MBA DIPLOMA AND OTHER COURSES 09810144315
.
ic
at
m
he 5
at 31
.m 44
w 1
w 0
w 81
09
ix.
x.
xi.
xii.
in
xiii.
xiv.
1
CONTACT FOR MATHEMATICS GROUP/HOME COACHING FOR CLASS 11TH 12TH BBA,BCA,
DIPLOMA CPT CAT SSC AND OTHER EXAMS Also home tutors for other subjects in south and west delhi
EMAIL:19 [email protected] web site www.mathematic.in
MATHEMATIC CENTER D96 MUNIRKA VILLAGE NEW DELHI 110067 & VIKAS PURI NEW DELHI
CONTACT FOR COACHING MATHEMATICS FOR 11TH 12TH NDA DIPLOMA SSC CAT SAT CPT
CONTACT FOR ADMISSION GUIDANCE B.TECH BBA BCA, MCA MBA DIPLOMA AND OTHER COURSES 09810144315
.
ic
at
m
he 5
at 31
.m 44
w 1
w 0
w 81
09
xv.
xvi.
xvii.
xviii.
xix.
in
20
CONTACT FOR MATHEMATICS GROUP/HOME COACHING FOR CLASS 11TH 12TH BBA,BCA,
DIPLOMA CPT CAT SSC AND OTHER EXAMS Also home tutors for other subjects in south and west delhi
EMAIL:20 [email protected] web site www.mathematic.in
MATHEMATIC CENTER D96 MUNIRKA VILLAGE NEW DELHI 110067 & VIKAS PURI NEW DELHI
CONTACT FOR COACHING MATHEMATICS FOR 11TH 12TH NDA DIPLOMA SSC CAT SAT CPT
CONTACT FOR ADMISSION GUIDANCE B.TECH BBA BCA, MCA MBA DIPLOMA AND OTHER COURSES 09810144315
.
ic
at
m
he 5
at 31
.m 44
w 1
w 0
w 81
09
xx.
in
21
CONTACT FOR MATHEMATICS GROUP/HOME COACHING FOR CLASS 11TH 12TH BBA,BCA,
DIPLOMA CPT CAT SSC AND OTHER EXAMS Also home tutors for other subjects in south and west delhi
EMAIL:21 [email protected] web site www.mathematic.in