Answer Key

2018-2019
Class: 11 Worksheet Number:11/Chem/12/AK
Subject: Chemistry Chapter: Organic Chemistry

Section A
Each question carries 1 mark :
1. Write the structural formula of the following:
(i) 4- Chloro – 2- pentene
(ii) p- Nitroaniline
(iii) 2,3-Dibromo-1-phenyl pentane
(iv) 4-Ethyl -1-fluoro -2-nitrobenzene
(v) Cyclohex-2-en-1-ol.

(i)

(ii) p-Nitroaniline

(iii) 2,3-Dibromo-1-phenyl pentane

(iv) 4-Ethyl -1-fluoro -2-nitrobenzene

(v) Cyclohex-2-en-1-ol.
2. Which of the following represents the correct IUPAC name for the compounds concerned ? (a)
2,2-Dimethylpentane or 2-Dimethylpentane (b) 2,4,7-Trimethyloctane or 2,5,7-Trimethyloctane
(c) 2-Chloro-4-methylpentane or 4-Chloro-2-methylpentane (d) But-3-yn-1-ol or But-4-ol-1-yne.

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3. Write all the acyclic and cyclic isomers having the molecular formula C3H6O

4. Draw formulas for the first five members of each homologous series beginning with the following
compounds. (a) H–COOH (b) CH3COCH3 (c) H–CH=CH2

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5. Give the IUPAC names of the following compounds

(i) CH3CH(Br)COCH(CH3)2 (ii) CH3CH(CHO)CH2CH(CH3)(COOH)
(iii) CH3COCH2CH2CHO (iv) CH3CH2CH(C2H5)CH2CH(CH3)CH2CH3
(v) CH= C-CH=CH-CH=CH2 (vi) CH3CH(NH2)CH2CH(C2H5)COOH
(vii) CH3CH(OH)CH2OCH3 (viii) CH3COCH(CH3) CH2CH2CH2Cl
(i)2-bromo-4-methylpentan-3-one
(ii)4-formyl-2-methylpentanoic acid
(iii)4-oxopentanal
(iv)3-ethyl-5-methylheptane
(v)Hexa-1,3-dien-5-yne
(vi)4-amino-2-ethylpentanoic acid
(vii)1-methoxypropan-2-ol
(viii)6-chloro-3-methylhexan-2-one
6. Write bond line formulas for :
(a)Isopropyl alcohol (b)2,3-Dimethyl butanal, (c)Heptan-4-one.

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7. Which of the following carbocation is the most stable ?

Tertiary carbocation (CH3)3C+ is the most stable carbocation due to the elctron releasing
effect of the three methyl groups. An increased +I effect due to the three methyl groups
stabilizes the postive charge on the carbocation.
8. Which of the following is not an electrophile ? OH- , SO3, NO2+, Cl+
OH- is not an electrophile, it is a nucleophile which can attack positive charge carbon atom.
Each question carries 2 marks :
9. Draw the structural formula and IUPAC names of the above compounds.

2-propylcyclohexane pent-4-yn-2-ol
10. Arrange the following compounds in increasing order of their property as indicated:
. (a) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid
strength)
(b) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid
strength)

(a)

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(b)

11. What do you understand by (i) Homolytic fission (ii) Heterolytic fission
(i)In homolytic fission, one of the electrons of the shared pair in a covalent bond goes with each of
the bonded atoms.

(ii)In heterolytic fission, the bond breaks in such a fashion that the shared pair of electrons remains
with one of the fragments

12. What is the relation between the following pairs? Are they structural or geometrical isomers or
resonance contributors?

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(a) Structural isomers (b)Geometrical isomers (c) Resonance contributors
13. Using curved-arrow notation, show the formation of reactive intermediates when the following
covalent bonds undergo heterolytic cleavage. (a) CH3–SCH3, (b) CH3–CN, (c) CH3–Cu

14. Explain the terms inductive and electrometric effects.

Inductive Effect :- Permanent electron displacement along a chain due to the presence of polar
covalent bond is known as Inductive effect.
If an atom or group attracts electron more strongly than hydrogen, it is said to have –I effect.
e.g. nitro (- NO2), cyano (- CN), carboxy (- COOH), ester (-COOR), aryloxy (-OAr, e.g. – OC6H5),
etc. are electron-withdrawing groups.
If an atom or group attracts electron less strongly than hydrogen it is said to have electron
releasing /donating group.
e.g. the alkyl groups like methyl (–CH3) and ethyl (–CH2–CH3) are usually considered as electron
donating groups.

Electromeric Effect:- This is a temporary effect which involves complete transference of the
shared pair of electrons to either of the two atoms linked by multiple bonds on the demand of the
attacking reagent.

15. Define. Give examples

(i)Metamerism
(ii)Position isomerism
(iii)Functional isomerism
(i)Metamerism: It arises due to different alkyl chains on either side of the functional group in the
molecule. For example, C4H10O represents methoxypropane (CH3OC3H7) and ethoxyethane
(C2H5OC2H5).

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(ii)Position isomerism: When two or more compounds differ in the position of substituent atom or
functional group on the carbon skeleton, they are called position isomers and this phenomenon is
termed as position isomerism. For example, the molecular formula C3H8O represents two alcohols:
CH3CH2CH2OH Propan-1-ol CH3−CH(OH)-CH3 Propan-2ol

(iii)Functional group isomerism: Two or more compounds having the same molecular formula but
different functional groups are called functional isomers and this phenomenon is termed as
functional group isomerism. For example, the molecular formula C3H6O represents an aldehyde
and a ketone.
16. What are electrophiles and nucleophiles? Explain with examples.
A reagent that brings an electron pair is called a nucleophile (Nu:) i.e., nucleus seeking and the
reaction is then called nucleophilic.
Examples of nucleophiles are the negatively charged ions with lone pair of electrons such as
hydroxide (HO– ), cyanide (CN- )and carbanions (R3C:–). Neutral molecules such as H2O etc., can
also act as nucleophiles due to the presence of lone pair of electrons.
A reagent that takes away an electron pair is called electrophile (E+) i.e., electron seeking and the
reaction is called electrophilic.
Examples of electrophiles include carbocations ( CH3 + ) and neutral molecules having functional
groups like carbonyl group (>C=O) or alkyl halides (R3C-X, where X is a halogen atom).
17. What are carbocations? Explain the order of relative stability of primary, secondary and tertiary
carbocations.
A species having a carbon atom possessing sextet of electrons and a positive charge is called a
carbocation (earlier called carbonium ion).
The CH3+ ion is known as a methyl cation or methyl carbonium ion.

Carbocations are classified as primary, secondary or tertiary depending on whether one, two or
three carbons are directly attached to the positively charged carbon.
Some other examples of carbocations are: CH3CH2+(ethyl cation, a primary carbocation),
(CH3)2CH + (isopropyl cation, a secondary carbocation), and (CH3)3C + (tert-butyl cation, a tertiary
carbocation).

Carbocations are highly unstable and reactive species. Alkyl groups directly attached to the
positively charged carbon stabilise the carbocations due to inductive and hyperconjugation effects,

The observed order of carbocation stability is:

CH3+(primary) < (CH3)2CH +(secondry) < (CH3)3C +(tertiary)
Thus tertiary carbocations are the most stable.
18. Identify the reagents shown in bold in the following equations as nucleophiles or electrophiles:

(a) OH -- Nucleophile as it is electron rich and nucleus seeking species.

(b) CN -- Nucleophile as it is electron rich and nucleus seeking species.
(c) CH3CO + Electrophile as it electron deficient.
19. Write structures of different chain isomers of alkanes corresponding to the molecular formula
C6H14. Also write their IUPAC names.

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Section B
Each question carries 1 mark :
20 Name each of the following compounds by IUPAC system
1) CH3-CH2-CHO Propanal

2) 3-chloro-1-nitrobutane
COOH
CH3

3) 2-methyl benzoic acid

4) (CH3)2 C(C2H5)2 3, 3-Dimethylpentane

5) 1,3-dimethylcyclohexene
OH
HO OH
6) Propane-1,2,3-triol

7) Octa-1,3,5,7-tetraene

8) 1-ethyl-3-iodobenzene

9) ClCH2-CCl3 1,1,1,2-Tetrachloroethane

10) 4-Phenylbut-1-ene

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11) Pent-1-ene-3-yne

12) CH3-CO-CH2-CH2-CH3 Pentan-2-one

Br

13) Cl 1-Bromo-3-chloro Benzene

OCH 3
Cl

14) CH3 2-chloro-4-methyl anisole

15) 4-Nitrobenzoic acid

OH
H3C O
16) CH3 1-Ethoxy propan-2-ol

17) 2-methyl-3-nitropentane
21. In which C-C bond of CH3CH2CH2Br, the inductive effect is expected to be the least?
Bond between C2 & C3. Magnitude of inductive effect diminishes as the number of intervening
bonds increases.
22. Out of benzene, m-dinitrobenzene and toluene which will undergo nitration most easily and why?
Order of ease of nitration is
Toluene > Benzene > m- dinitrobenzene
Nitration is an electrophilic substitution reaction. Since methyl group is electron releasing group
,i.e. activating, it increases electron density on the benzene ring thereby facilitating electrophilic
substitution reaction. Nitro group on the other hand is electron withdrawing group, therefore it is
deactivating i.e. decreases the reactivity towards electrophilic substitution reaction

> >
23. (CH3)3C+ is more stable than (CH3)2CH+. Explain, Why?
Due to hyper conjugation and +I effect
24. Why do SO3 act as an electrophile?
Since oxygen is more electronegative than ‘S’, therefore, ‘S’ is positively charged and acts as a
electrophile.

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25. Which of the following species act as a nucleophiles?

NH3, BF3, +NO2, C2H5O-
NH3, C2H5O- act as a nucleophiles
As these species have unshared pairs of electrons which can be donated or shared with an
eletrophile.
26. Write the metamer of diethyl ether . What is its IUPAC name?
CH3OCH2CH2CH3 1-methoxypropane
CH3OCH(CH3)2 2-methoxypropane
27. Ethyne is stronger acid than propyne .Explain.
This is because of the +I effect of the methyl group which tends to increase the electron density
on the triple bonded carbon atom in propyne. The release of H+ ion from propyne is more difficult
than from ethyne or it is a weaker acid than ethyne.
H--CC—H (Ethyne)
CH3---CC---H (Propyne)
28. Electromeric effect is a temporary effect. Give reason.
The electromeric effect is seen in organic compound s containing multiple bonds (-C=O, -C=C-,-
CC-) under the influence of attacking reagent. The moment, the attacking reagent is removed, pi
electron pair comes back to its original position forming multiple bonds again.
Hence electromeric effect is a temporary effect.
29. Alcohols are weaker acids than water. Why?
In Alcohols (R-OH), the alkyl group has +I effect. It increases the electron density on the oxygen
atom. As a result, the release of H+ ion from alcohol is more difficult than from water .Hence
alcohols are weaker acids than water.
30. Ethylamine is a stronger base than acetamide. Give reason.
In acetamide, the carbonyl group is elctron withdrawing in nature. It decreases the electron density
on the N-atom of the amino group due to conjugation.
On the other hand, in ethylamine, ethyl group has +I effect and it increases the electron density on
N-atom. Hence electron releasing tendency is more in ethylamine than in acetamide.
Therefore ethylamine is a stronger base than acetamide.

(acetamide) CH3CH2NH2
(ethylamine)
31. Higher alkyl substituted alkene is formed in greater proportion than the lower alkyl substituted
alkene. Justify.

In alkyl substituted alkene, the α- (alpha) hydrogen atoms of the methyl group are involved in the
hyperconjugation with the pi() electron pair of the double bond. As a result, the stability of the
alkene increases. Greater the number of such groups more will be the stability of alkene. Thus, the
relative order of stability of alkenes is

CH3—CH=CH—CH3 (But-2-ene) > CH3-CH=CH2 (Propene) > CH2=CH2 (Ethene)

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32. Write the structural formula for the following compound:-

1 5-(2,2– Dimethylpropyl)nonane

2 2-Methyl phenol

3 1-bromo-2-methylcyclohexane

4 1-cyclopropyl-3-
methylcyclobutane

5 2,2-dichloropropane H3C
Cl
Cl CH3
6 Methoxy ethane CH3-O-CH2-CH3
7 Methoxy methane CH3-O-CH3
8 Butanoic acid CH3-CH2-CH2-COOH
9 Ethanoyl chloride CH3-COCl
10 Methyl ethanoate CH3-COOCH3
11 Propanamide CH3-CH2-CONH2
12 Methanamine CH3-NH2
13 Ethanenitrile CH3-CN
14 Ethane-1,2-dial OHC--CHO
15 3-Methyl pentanenitrile CH3
H3C CN
16 2-Methoxypropan-1-al OCH3

H3C CHO
17 2-Methyl butanoic acid

18 But-2-en-1-oic acid CH3-CH=CH-COOH

19 3-Bromo-5-methyl hexan-2-ol HO

H3C CH3

CH3 Br
20 2-methyl-4-nitropentan-2-ol H3C CH3
OH
NO 2 CH3

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21 2-Bromophenyl Ethanal CHO

Br

22 3-hydroxycyclohexan-1-one O

OH
23 Cyclohexyl benzene

24 1-Phenyl propan-1-one CH3

O

25 2,4,6-Trinitrophenol (Picric acid) OH

O 2N NO 2

NO 2
26 4-hydroxy-3-methoxy CHO

benzaldehyde

OCH 3
OH
27 3,4-dimethyl phenol OH

CH3
CH3

Each question carries 2 marks :

33. Which electron displacement effect explains the following correct orders of acidity of the
carboxylic acids?
(i)Cl3CCOOH > Cl2CHCOOH > ClCH2COOH
(ii)CH3CH2COOH > (CH3)2CHCOOH > (CH3)3CCOOH
(i)Cl is electron withdrawing group and it shows negative inductive effect therefore stabilizes
intermediate carboxylate ion, thus, acidic character increases with increase in the number of
chlorine atoms, because stability of carboxylate ion increases.
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(ii)Methyl is electron releasing group and it shows positive inductive effect hence will destabilize
carboxylate ion due to which acidic character decreases with increase in number of alkyl groups
34. Identify the electrophile center in CH3-CHO
O-

CH3-C+--H

‘C’ is positively charged therefore, it is electrophilic center.

35. What is the type of hybridization of each carbon in the following?
(i) CH3Cl (ii) (CH3)2CO (iii) HCONH2(iv) CH3CH=CH-CN
(i)C-H -sp3 (ii)C-Hsp3, C=O sp2, C-Hsp3 (iii)C=O sp2 (iv)C-Hsp3 C=C sp2 C=Csp2 C= N sp
36. Which bond is more polar in the following pairs of compound :
(i) H3C--H , H3C--Br (ii) H3C--NH2,H3C--OH (iii) H3C--OH ,H3C--SH
(i)C–Br, since Br is more electronegative than H.
(ii)C-O, since O is more electronegative than N
(iii)C–O, since O is more electronegative than S
37. Classify the following reactions according to the reaction type
(i) CH3CH2Br + HS- → CH3CH2SH + Br-
(ii) (CH3)2C = CH2 + HCl → (CH3)2C(Cl)-CH3
(iii) CH3CH2Br + OH- → CH2= CH2 + HBr
(iv)CH3C(C6H5)= NOH → CH3CONHC6H5
(i)substitution reaction
(ii)addition reaction
(iii)elimination reaction
(iv)rearrangement reaction
38. Arrange the following
(i)(CH3)3C+, CH3CH2CH+, CH3CH2CH2CH2+ : [increasing order of stability]

CH3
(ii) –I, -Br, -Cl, -F [decreasing order of –I effect]
(i) CH3CH2CH2CH2+ < CH3CH2CH+ < (CH3)3C+

CH3
This is because of greater + I effect and greater hyperconjugation seen in case of t-butyl cations .

(ii)F > Cl > Br > I

Fluorine being the most electronegative shows greater –I effect
Each question carries 3 marks :
39. Draw the structural formula of the following:
(i) 2-Phenylpropene (ii) 2-cyclopropylbutan-1-ol (iii) 3-Amino-2-oxopent-4-enoic acid

OH
(i) (ii) H3C (iii)
40. Draw the resonance structures of the following compounds.

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(a) Phenol (b) Aniline (c) Chlorobenzene

41. (a) How does hyperconjugation explain the stability of alkenes?

(b) Arrange the following in increasing order of stability.
2-Methylbut-2-ene, but-2-ene and 2,3-Dimethylbut-2-ene
(a) Hyperconjugation is a general stabilising interaction. It involves delocalisation of σ electrons of
C—H bond of an alkyl group directly attached to an atom of unsaturated system or to an atom with
an unshared p orbital.
The σ electrons of C—H bond of the alkyl group enter into partial conjugation with the attached
unsaturated system or with the unshared p orbital.
Hyperconjugation is a permanent effect.
Delocalisation of electrons by hyperconjugation in the case of alkene can be depicted as in Fig.

There are various ways of looking at the hyperconjugative effect. One of the way is to regard C—
H bond as possessing partial ionic character due to resonance.

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In general greater the number of alkyl group attatched to the unsaturated system, greater is the
hyperconjugation interaction and stabilization of the alkene.

(b) < <

Greater the number of hyperconjugative structures more stable is the alkene.
As more number of hyperconjugative structures are possible for 2,3-Dimethylbut-2-ene it is the
most stable.

Section C
Each question carries 1 mark :
42. Arrange the following compounds in increasing order of their acid strength:
Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.
Propan-1-ol < 4-methylphenol < phenol < 3-nitrophenol < 3,5-dinitrophenol < 2,4, 6-trinitrophenol
(Electron withdrawing groups in phenol increase its acidic strength and electron releasing groups
decrease it.)
43. Arrange the three isomeric xylenes in the increasing order of their polarity.

p-xylene < m-xylene < o-xylene

ortho xylene is most polar due to the large electron density at one side of the molecule
44. Write resonance structures of CH2=CH–CHO. Indicate relative stability of the contributing
structures.

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I: Most stable, more number of covalent bonds, each carbon and oxygen atom has an octet and no
separation of opposite charge
II: negative charge on more electronegative atom and positive charge on more electropositive atom
III: does not contribute as oxygen has positive charge and carbon has negative charge, hence least
stable.
45. Explain why alkyl groups act as electron donors when attached to a -system.
Alkyl group has sp3 hybridization whereas  - bonded atom is sp2 hybridized which is more
electronegative, therefore, alkyl group act as electron donors.
46. Arrange the following in increasing order of basic strength:
C6H5NH2, (C2H5)2NH and CH3NH2
Due to the –R effect of the –C6H5 group, the electron density on the N atom in –C6H5NH2 is lower
than that on the N atom of C2H5NH2.Hence the given compounds can be arranged in the increasing
order as follows.
C6H5NH2 < CH3NH2 < (C2H5)2NH
47.
OCH2CH3

Write the metamers of

CH3 H3C

CH2OCH3 OCH 3 OCH 3H C OCH3

3

48. Cyclohexylamine is more basic than aniline. Explain.

Both are Lewis bases. In aniline the electron pair on the N-

atom is involved in conjugation with the pi-() electron pairs of the ring. As a result, the
electron density on the N-atom is reduced whereas in cyclohexylamine the electron pair on
N-atom is not involved in any conjugation.
Hence cyclohexylamine is a stronger base.

49. Which of the two: O2NCH2CH2O– or CH3CH2O– is expected to be more stable and why ?

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Each question carries 2 marks :

50. With proper justification, arrange the following in the order of increasing stability.
-
CH3CH2-- , HC C , CH2=CH--
-
In HC C ion , the C atom carrying the –ve charge is sp hybridized and has 50 % s-character, in
CH2=CH—ion the C atom is sp2 hybridized and has 33.3% s-character while in CH3CH2-- ion ,
the carbon atom bearing –ve charge is sp3 hybridised and has 25% s- character.
Since s-electrons are closer to the nucleus than p-electrons, hence C-atom with greater s-character
can accommodate or stabilize the negative charge better than the C-atom with smaller s-character.
Thus stability of the carbanion increases as the s-character of the C-atom carrying –ve charges
increases.
-
Thus CH3CH2-- < CH2=CH-- < HC C
51. Give the IUPAC names of the following compounds :

(a)(1-Propane)benzene
(b)3-methylpentane-1-nitrile
(c)2,5-dimethylheptane
(d)3-bromo-3-chloroheptane
(e)3-chloropropanal
(f)2,2-dichloroethan-1-ol
52. For the following bond cleavages, use curved-arrows to show the electron flow and classify each
as homolysis or heterolysis. Identify reactive intermediate produced as free radical, carbocation
and carbanion.

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53. Although phenoxide ion has more number of resonating structures than carboxylate ion,
carboxylic acid is a stronger acid than phenol. Why?

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Each question carries 3 marks :

54. Draw the resonance structures for the following compounds. Show the electron shift using curved-
arrow notation.
(a) C6H5OH (b) C6H5NO2 (c) CH3CH=CHCHO (d) C6H5–CHO (e) C6H5-CH2+(f) CH3CH
=CHCH2+

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55. Which acid of each pair shown here would you expect to be stronger?

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