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Dipawali Home Assignment

Course : AJAY (ER)

Sub: Organic Chemistry (2014-2015)

1.

In which of the following first resonating structure is more stable than the second ?
(1)

(2)

(3) CH2=CHNH2
2.

(3) b > c > a > d

(4) a > b > d > c

(2)

C=CH2

(3) CH2 = CH N

(4)

The correct stability order of following species is :

(1) x > y > w > z


(3) x > w > z > y
5.

(2) d > c > a > b

In which of the following C = C bond length is minimum :


(1)

4.

The decreasing order of bond length of double bonds is :

(1) c > a > b > d


3.

(4)

(2) y > x > w > z


(4) z > x > y > w

The correct stability order of the following resonance structures is :

(1) (IV) > (I) > (III) > (II)


(3) (III) > (II) > (IV) > (I)

RESONANCE

(2) (II) > (IV) > (I) > (III)


(4) (I) > (IV) > (III) > (II)

PAGE # 1

6.

The correct IUPAC name of the compound is :

(1) (3-Aminomethyl-5-hydroxymethylcyclohexyl)methanesulphonic acid.


(2) (3-Hydroxymethyl-5-sulphomethylcyclohexyl)methanamine
(3) (3-Aminomethyl-3-sulphomethylcyclohexyl)methanol
(4) 3-Aminomethyl-5-hydroxymethyl-1-sulphomethylcyclohexane
7.

The correct IUPAC numbering in main chain in the compound is :

(1)
8.

(2)

(3)

(4)

The correct IUPAC name of the compound is :

(1) 2, 3-Dibromo-3, 6-dichlorodicyclohexane


(2) 1-Bromo-2-(3-bromo-5-chlorocyclohexyl)-3-chlorocyclohexane
(3) 1-Bromo-3-(2-bromo-6-chlorocyclohexyl)-5-chlorocyclohexane
(4) 2-Bromo-1-(3-bromo-5-chlorocyclohexyl)-6-chlorocyclohexane
9.

Correct IUPAC name of following compound is

(1) 5,8,9-Triethyl-4,7-Bis(1,1-Dimethylpropyl)-2,3-dimethylundecane
(2) 4,7-Bis(1,1-Dimethylpropyl)-5,8,9-triethyl-2,3-dimethylundecane
(3) 7-(1,1Dimethylpropyl)-4-(1,2dimethylpropyl)-5,8,9-triethyl-3,3-dimethylundecane
(4) 5-(1,1-Dimethylpropyl)8-(1,2-dimethylpropyl)-3,4,-7-triethyl-9-,9-dimethylundecone
10.

How many acyclic esters have molecular formula C4H6O2 (only structural isomers considered)
(1) 2
(2) 3
(3) 4
(4) 5

11.

The degree of unsaturation in the following compounds is

(1) 4

RESONANCE

(2) 3

(3) 2

(4) 5

PAGE # 2

12.

Which of the following pair is the chain isomer ?

(1)

13.

15.

16.

(3)

(4)

How many products (structural isomers) are formed by monochlorination of ?

(1) 13
14.

(2)

(2) 12

(3) 15

(4) 14

Compounds I and II can be distinguished by using reagent.

4-Amino-2-methylbut-3-en-2-ol
(1) NaNO2 / HCl

4Amino2,2-dimethylbut- 3-yn-1-ol.
(2) Br2 / H2O

(3) HCl / ZnCl2 (anhydrous)

(4) Cu2Cl2 / NH4OH

Which of the following statement is incorrect :


(1) Tollens reagent can distinguish propene and propyne
(2) Iodoform test can distinguish propanone and ethanal
(3) Lucas reagent can distinguish 1-propanol and 2-propanol
(4) NaHCO3 can distinguish phenol and benzoic acid.

O
O
O
||
||
||
O / Zn, H2O
H C CH2 C CH2 C H + HCHO
X 3
The structure of X will be :

(1)

17.

(2)

(3)

(4)

(3) 22

(4) 24

Number of -bond in the given compound is :

(1) 18

RESONANCE

(2) 20

PAGE # 3

18.

Among these groups, which of the following orders is correct for the magnitude of their + effect ?
(1) > >
(2) > >
(3) > >
(4) > >
19.

IUPAC name of the following compound is :

(1) 1,2-Dibromo-3-chlorocycloprop-1-ene
(3) 1,2 Dibromo-3-chlorocycloprop-2-ene

20.

(2) 1,3-Dibromo-2-chlorocycloprop-1-ene
(4) 2,3-Dibromo-1-chlorocycloprop-1-ene

The correct relation between above compounds is :


(1) Position isomers
(2) Homolog
(3) Functional isomers
21.

(1) 4-Bromo-3-cyanophenol
(3) 2-Cyano-4-hydroxybromobenzene
22.

(4) Metamers

The IUPAC name of the following compound is :

(2) 2-Bromo-5-hydroxybenzenecarbonitrile
(4) 6-Bromo-3-hydroxybenzonitrile

H / Ni

2
Cl2 / h
X
C8H16
3 mono chloro structural product

Structure of X will be :

(1)

RESONANCE

(2)

(3)

(4)

PAGE # 4

23.

Which of the following relation is incorrect.

(1)

and

(2)

and

(3)

are position isomers.

and

(4)

24.

are position isomers.

are chain isomers.

and

are geometrical isomers

Which of the following are functional isomers of methyl ethanoate ?

(a) CH3 CH2 COOH

O
||
C

(b) CH3
CH
|
OH

(1) a, b, c & d
(3) a & b
25.

O
||
(c) CH 3 O CH 2 C H

O
||
(d) CH2 C CH3
|
OH

(2) a, b & c
(4) a only

The given compound can not show :


H
==
Br

Cl

(1) Positional isomerism


(3) Optical isomerism

(2) Geometrical isomerism


(4) Metamerism

26.

The INCORRECT statement about a pair of geometrical isomers.


(1) They are diastereomers of each other.
(2) They are mirror image of each other.
(3) They have different boiling points.
(4) They can be separated by physical methods of separation.

27.

The smallest unsaturated Acyclic aldehyde and its next homologue are reacted with NH2OH to form oximes.
(1) Two different oxime are formed
(2) Four different oxime are formed
(3) Three different oxime are formed
(4) Only one oxime is formed

28.

Which of the following is Z-isomer :

(1)

RESONANCE

(2)

(3)

(4)

PAGE # 5

29.

and

(1) Chain isomers


30.

(2)

(3) Homologs

(4) Identicle

(3)

(4)

Which of the following is the structure of (S)-Pentan-2-ol is ?

(1)

32.

(2) Enantiomers

Mark out the optically inactive molecule :

(1)

31.

are :

(2)

(3)

(4)

(3) 6

(4) 8

Total number of stereoisomer of compound is :

CH CH CH CH CH
|
Cl
(1) 2
33.

(2) 4

Which is the incorrect relationship mentioned in bracket :


(1) CH3 CN and CH3NC
(2) CH3 CH2 O CH2 CH3 and CH3 CH2 CH2 O CH3

(functional isomers)
(Metamers)

(3) CH3 CH2 CH2 CHO and H3C CH CH3

(Chain isomer)

(4) CH3CH2OH and CH3OCH3

(Metamers)

|
CHO

34.

The correct IUPAC Name of

is

(1) 5-carboxy-3-oxocyclohexane carboxaldehyde


(2) 2-carboxy-5-formylcyclohexane
(3) 4-formyl-2-oxocyclohexane carboxylic acid
(4) 4-carboxy-3-oxocyclohexanal
35.

Which species does not exhibit a plane of symmertry ?

(1)

RESONANCE

(2)

(3)

(4)

PAGE # 6

36.

The most stable conformation is :

(1)

37.

(2)

(3)

(4)

How many meso steroisomers are possible for 2, 3, 4Trichloropentane


(1) 1
(2) 2
(3) 3

(4) None

Paragraph for Question Nos. 38 to 39


X is the lowest molecular weight acyclic ester with saturated chain which can show metamerism. Y is an
isomeric carboxylic acid of next higher homolog of X.
38.
39.
40.*

What is the number of metamers of X ?


(1) 2
(2) 3

(3) 4

(4) 5

Total number of structurally isomeric carboxylic acid of Y is.


(1) 2
(2) 3
(3) 4

(4) 5

Which of the following is/are correct about the isomers?


(1) Four structurally isomeric acids are possible of formula C5H10O2.
(2) Four structurally isomeric aldehydes are possible of formula C5H10O.
(3) Nine structurally isomeric esters are possible of formula C5H10O2.
(4) Three structurally isomeric ketones are possible of formula C5H10O.

41.*

Which of the following pairs have same general formula ?


(1)

(3)

&

&

(2)

&

HC C C CH

(4)

&

42.*

Which statements for relationship are correct?


(1) Propanone and propanal are functional isomers
(2) Ethoxyehtane and 1-methoxypropane are metamers
(3) Isobutanol and neopentanol are homologs
(4) Ethylpentane and trimethylbutane are chain isomers

43.*

Which of the following will give positive iodoform test.


(1)

44.*

(2)

(4)

The compounds which are resonance stabilised are

(1) CH2=CHCl

45.*

(3)

(2)

(3) CH2 = CH CH2 Cl

(4)

The correct number of p-electrons have been mentained in :

(1)

RESONANCE

; (4)

(2)

; (6)

(3)

; (3)

(4)

; (6)
PAGE # 7

46.

Column-I

Column-II

(Stability order)

(Responsible effect)

(1)

>

(2)

(p) Inductive effect

>

(q) Resonance

(3) CH3CH2 >

(r) Hyperconjugation

(4)

(s) Steric repulsion

> CH3CH2

47.

Number of electrons in resonance in the following structure is.

48.

Find the number of total structurally isomeric cyclic isomers of C3H6O.

49.

Find the number of total structurally isomeric cyclic ethers with molecular formula C4H8O.

50.

How many groups show effect?

NH3 , CH2 , OH, N(CH3)2 , SO3H, CHO, Cl, CH3 , COO , O

ANSWER KEY
1.

(3)

2.

(4)

3.

(2)

4.

(3)

5.

(4)

6.

(1)

7.

(3)

8.

(2)

9.

(2)

10.

(4)

11.

(1)

12.

(2)

13.

(1)

14.

(3)

15.

(2)

16.

(2)

17.

(3)

18.

(4)

19.

(2)

20.

(4)

21.

(2)

22.

(4)

23.

(1)

24.

(1)

25.

(4)

26.

(2)

27.

(3)

28.

(1)

29.

(4)

30.

(3)

31.

(3)

32.

(2)

33.

(4)

34.

(3)

35.

(4)

36.

(1)

37.

(2)

38.

(1)

39.

(1)

40.*

(1, 2, 3, 4)

41.*

(1, 2, 3, 4)

42.*

(1, 2, 3, 4)

43.*

(2, 3, 4)

44.*

(1, 2, 4) 45.*

(1, 2, 3, 4)

46.

(1) s ; (2) p, q, r ; (3) p ; (4) p, r

47.

8e

48.

49.

RESONANCE

50. 6

PAGE # 8