Test Date: 08.02.2015 (Sunday) Time : 11:00 am to 01:00 pm · PDF fileWhich of the following is not an electrophile? a

Dr. Sangeeta Khanna Ph.D 1 CHEMISTRY COACHING CIRCLE C:\Users\Sahil\Desktop\Obj-Grand Test - 7.doc

Test Date: 08.02.2015 (Sunday) Time : 11:00 am to 01:00 pm

Test Venue:

Lajpat Bhawan, Madhya Marg, Sector 15-B, Chandigarh

Dr. Sangeeta Khanna Ph.D


Test Date 8.2.2015

READ THE INSTRUCTIONS CAREFULLY

1. The test is of 2 hours duration.

2. The maximum marks are 192.

3. This test consists of 59 questions. 4. For each question in Section - A, B & C you will be awarded 3 marks if you have darkened only the

bubble corresponding to the correct answer and zero mark if no bubbles are darkened. Minus one

(-1) mark will be awarded for wrong answer

5. For each question in Section–D (More than One Answer), you will be awarded 3 marks for each correct

answer. There is no negative marks awarded for incorrect answer(s) in this Section.

6. For each question in Section–E (Matrix Match), you will be awarded 2 marks for each row in which you have darkened the bubble(s) corresponding to the correct answer. Thus, each question in this

section carries a maximum of 8 marks. There is no negative marks awarded for incorrect answer(s)

in this Section.

7. For each question in Section F (Integer Type), you will be awarded 3 marks if you darken the

bubble corresponding to the correct answer and zero mark if no bubble is darkened. No negative marks will be awarded for in this Section.

8. Keep Your mobiles switched off during Test in the Halls.

SECTION – A (Single Option Correct)

This Section contains 34 multiple choice questions. Each question has four choices A), B), C) and

D) out of which ONLY ONE is correct. (Mark only One choice) 34 × 3 = 102 Marks

1. The IUPAC name of is

a. 3-vinyl-3-ethyl-2-propene b. 3-Ethyl-3-vinylprop-2-ene c. 3-Ethylpenta-1, 3-diene d. none C

2. The IUPAC name of the compound is :

a. Toluene carbonyl chloride b. 3-Methyl benzene carbonyl chloride c. 5-Methyl benzoyl chloride d. 5-Methyl benzene carbonyl chloride B

3. The IUPAC name of

is

a. 6-carboxy-2, 3-dimethyl-4-heptenoic acid b. 2, 3, 6-trimethyl-4-heptene-1, 7-dioic acid c. 2, 5, 6-trimethyl-3-heptenedioic acid d. 6-carboxy-2, 5-dimethyl-3-heptenoic acid C

4. The IUPAC name of C6H5CH = CHCOCH3 is

a. 4-Phenylbut-3-en-2-one b. 1-Phenylbut-1-en-3-one c. 2, 5, 6-trimethyl-3-heptenedioic acid d. 2-Oxo-4-Phenylbut-3-ene A

C = CH – CH3

H5C2

CH

CH2

COOH

COOH

COCl

CH3



5. An electrophilic reagent must have

a. a vacant orbital b. an orbital containing one electron c. an orbital containing two electrons d. a positive charge on it A

6. The hybridization states of the carbon atom (1) and carbon atom (2) in the compound

2

321

HCHCCN

are respectively

a. sp2 and sp b. sp3 and sp c. sp and sp2 d. sp and sp C

7. The IUPAC name of the compound

a. 3, 3-Diethyl-4-methyl-5-isopropyl octane b. 3, 3-Diethyl-5-isopropyl-4-methyl octane c. 4-Isopropyl-5-methyl-6,6-diethyl octane d. 6,6-Diethyl-4-isopropyl-5-methyl octane B

8. Among the following carbon radicals, the stability decreases in the order

a. (CH3)3C > CH2 = CH – CH2 > (CH3)2CH > CH3CH2 b. (CH3)3C > (CH3)2CH > CH2 = CH – CH2 > CH3CH2 c. CH2 = CH – CH2 > (CH3)3C > (CH3)2CH > CH3CH2 d. (CH3)3C > (CH3)2CH > CH3CH2 > CH2 = CH – CH2 C

9. Which of the following chemical systems is/are nonaromatic?

a. II b. IV c. II and IV d. None of the above A

10. Which of the following is aromatic?

a. b. c. d. D

11. Cyclopentadiene is much more acidic than cyclopentane. The reason is that

a. cyclopentadiene has conjugated double bonds b. cyclopentadiene has both sp2 and sp3 hybridized carbon atoms c. cyclopentadiene is a strain-free cyclic system d. cyclopentadienide ion, the conjugate base of cyclopentadiene, is an aromatic species and hence

has good stability D

Sol.

CH3CH2CH2CH – CH

CH

CH3

C – CH2CH3

CH2CH3

CH2CH3 CH3 CH3

I III II

N

H

N

H

N

Θ

H + Θ

Aromatic

IV

H

B



12. Which of the following is not an electrophile?

a. 4NH b. BF3 c. AlCl3 d. all are electrophile

A 13. Which of the following is the correct order of decreasing stability?

a. CH ΘC > CH2 = ΘCH > CHΘ3

b. CHΘ3

> CH2 = ΘCH > CH ΘC

c. Θ2

ΘΘ3 CHCHCCHCH d. CH2 = Θ

3ΘΘ CHCCHCH

A

14. Which of the following statement is CORRECT regarding the inductive effect?

a. it implies the atom’s ability to cause bond polarization b. it implies the transfer of lone pair of electrons from more electronegative atom to the lesser

electronegative atom in a molecule c. it implies the displacement of lone pair of electrons from less electronegative atom to the more

electronegative atom in a molecule d. it increases with increase in distance C

15. Which of the following is the correct order of stability of following carbocation?

a. I > II > III > IV b. III > IV > I > II c. III > I > IV > II d. II > III > IV > I B

16. Which of the following is the correct order of increasing +M effect?

a. b.

c. d. A 17. Which of the following carbanion is least stable?

a. b. c. d. C

CH2 CH2

NO2

CH2

OCH3

CH2

CH3

CH2

(I)

;

CH2

C N

(II)

;

CH2

OH

(III)

;

CH2

(IV)

CH3

O

>

NH2

>

OH OH

>

NH2

>

O

> >

NH2 O OH

>

OH O NH2



18. In which of the following Benzene ring is most activated for electrophilic attack.

a. b. c. d. B 19. Which of the following position is reactive for electrophilic attack a. 1, 3, 8 b. 1, 3, 5 c. 10, 8, 6 d. 1, 3, 6

B 20. Which of the following compound is meta directing due to reverse Hyperconjugation effect.

a. b. c. d.

B 21. Which alkene is most stable.

a. b. c. d. C

22. The IUPAC name of OH

CH

CH

CCH)OH(CHCH

3

3

|

|23 is

a. 1, 1-Dimethyl-1, 3-butanediol b. 2-Methylpentane-2, 4-diol

c. 4-Methyl-2, 4-pentanediol d. 1,3,3-Trimethyl-1,3-propanediol B

23. The compound 3

3

|

3

|3 CHH

CH

CH

CH

CCH have

a. Twelve 1° hydrogen atoms only b. Two 2° and twelve 1° hydrogen atoms c. Two 3° hydrogen atoms only d. Twelve 1°- and Two 3°-hydrogen atoms D

24. The compound in which C uses only its sp3 hybrid orbitals for bond formation is a. HCOOH b. (NH2)2CO c. (CH3)3COH d. CH3CHO C 25. Following compound contains three C = C, arrange these in stability order: a. a > b > c b. c > b > a c. b > a > c d. c > a > b

CH3

NH – C

1 2

3

4 5

O 10 9

8

7 6

CN CCl3 CH3 NO2

CH3

C = C

H

H CH3

CH3

CH3

C = CH2

CH3

CH3

C = C

CH3

CH3

CH3

H3C

C = C

CH2

CH3

CH3

C C C C C

CH3 CH3

H

H

CH3 CH3

a

a b

c

C CH3

OH O – C – CH3

O

NH – C – H

O



C Sol. As the number of hyperconjugative structure increases in alkene stability also increases so order is

b > a > c 26. Which of the following resonating structures is most unstable?

a. b. c. d. B

Sol. (b) is most unstable because both parts of cycle are Anti aromatic 27. The correct order of nucleophilicity is:

a. FOHNHCH 23 b. 23 NHCHOHF

c. 32 CHFNHOH d. 32 CHNHOHF

D

28. Degree of unsaturation in is:

a. 2 b. 3 c. 4 d. 5

C

29.

Arrange the (C–H) bonds x, y & z in decreasing order of their bond dissociation energies in homolysis.

a. y > x > z b. z > x > y c. z > y > x d. y > z > x

B

Sol

so bond dissociation energy order is E1 < E2 < E3

30. The total number of lone pair of electrons in the molecule given is:

a. 2 b. 3 c. 4 d. 5

B

Sol. Total ‘3’ P in molecule

CH2

CH2

H H x

H H

y

H

z

H x

H y

z

H

Highly unstable

Stable due to hyper conjugation

Stable due to resonance +

hyperconjugation

E3 E2

E1

N – H

O

N – H

O



31. The functional groups present in Cortisone are:

a. Ether, alkene, alcohol b. Alcohol, ketone, alkene, ether

c. Alcohol, ketone, ester d. Ether, amine, ketone

B

32. Which of the following alkenes is the most stable?

a. b. c. d.

C

Sol. Stability of Alkene No. of ‘’ H atoms or more hyper conjugation & resonance.

33. Which one among the following carbocations has the longest life?

a. b. c. d.

A

Sol. most stable C due to ‘’ resonance or bent bond overlapping 34. Identify the correct statement.

a. /\

\/ CC and OC\

/ undergo nucleophilic addition

b. /\

\/ CC and OC\

/ undergo electrophilic addition

c. /\

\/ CC undergoes electrophilic addition but OC\

/ undergoes nucleophilic addition

d. /\

\/ CC undergoes nucleophilic addition but OC\

/ undergoes electrophilic addition

C

Sol. /\

\/ CC undergoes electrophilic addition but OC\

/ undergoes nucleophilic addition

CH3

HOH2C

O

O

OCH3

Cortisone

C

C

C

CH3 – C – CH3

CH3

C



SECTION – B (Assertion and Reason)

This Section contains 3 multiple choice questions. Each question has four choices A), B), C) and D) out of which ONLY ONE is correct. 3 × 3 = 9 Marks

(A) If both the statements are true and statement-2 is the correct explanation of statement – 1. (B) If both the statements are true but statement-2 is not the correct explanation of statement – 1. (C) If statement – 1 is True and Statement – 2 is False. (D) If statement – 1 is False and statement – 2 is True. 1. Assertion: 7-Bromo-1, 3, 5-Cycloheptatriene exists as ionic compound.

Reason: Tropylium ion is Anti aromatic and is stable a. (A) b. (B) c. (C) d. (D) C

Sol.

2. Assertion: OCR is more stable than R – C+ = O.

Reason: In 1st structure positive charge is present on oxygen atom a. (A) b. (B) c. (C) d. (D)

B

3. Assertion: IUPAC name of the compound

32 3

| |33

CHCHCH

CHCHCCHCCCH

is 3-ethyl-4-methylhept-

2-en-5-yne Reason: Double bond is given preference over triple bond if both gets same position. a. (A) b. (B) c. (C) d. (D) A

SECTION – C (Comprehension Type)

This Section contains 1 Comprehension. Each of these questions has four choices A), B), C) and D) out of which ONLY ONE is correct. 4 × 3 = 12 Marks

Passage – 1 Carbocation is a group of atoms with positively charged carbon atom having six electrons in the valence shell after sharing. Carbocations are formed in the heterolysis of a bond and are planar species. Stability of carbocation is determined by inductive effect, hyperconjugation and resonance effect. Greater the number of contributing structures, more is the stability of a Carbocation. Electron releasing groups (+I effect) increases the stability of a carbocation whereas the electron withdrawing groups (-I effect) have an opposite effect.

1. Which of the following is most stable carbocation?

a. 3HC

b. 33 CHHCCH

c. 23 HCOCH

d. 23 HCSCH

C

Tropylium ion (stable due to resonance)

Br H

+ Br –



2. The most stable carbocation among the following

a. b. c. d.

C 3. The most stable and the least stable carbocation among

(I) (II) 22 HCCHCH

(III) 256 HCHC

and (IV) 33 CHHCHC

are respectively:

a. II, I b. III, IV c. I, II d. I, IV D

4. Most stable carbocation is formed by the heterolysis of

a. (CH3)3CBr b. (C6H5)3CBr c. (C6H5)2CHBr d. C6H5CH2Br. B

SECTION – D (More than One Answer Type)

This Section contains 5 multiple choice questions. Each question has four choices A), B), C) and D) out of which ONE OR MORE may be correct. 5 × 3 = 15 Marks

1. Which of the following represents functional isomers?

a. Alcohols and ether b. Nitroalkanes and alkyl nitrites (R – O – N = O) c. Aldehyde and Ketone d. Glucose and fructose A,B,C,D

2. Some pairs of acids are given below. Select the pair in which second acid is stronger than first

a. CH3CO2H and CH2FCO2H b. CH2FCO2H and CH2ClCO2H

c. OHH

NO

C ; OHH

lC

C 2

2

|2

|

d. COOHCHH

F

CCH & HCOOH

F

CCHCH 2|

3|

23

A, C Sol. With the increase in –I of group acidic strength increases. 3. In which of the following cases, the carbocation (I) is less stable than the carbocation (II),

a. b.

c. )II(HCCH ),I(HCCH 232

d. 22|

23 HCH

F

C ),I(HCCH

A, C

+

NO2

CH2 +

(I),

CH2 +

(II)

CH2

NO2

,

CH2

OCH3



4. Which of the following reaction is not correctly matched.

a.

b. AdditionlicelectrophiCH

CH

Cl

CCHCH

CH

CCH 3

3|

|3

HCl2

3|

3

c. on]substituti licelectrophi[ CHH

OH

CCHCHH

Cl

CCH 3|

3KOH

.aq3

|3

d. ion]ilic Addit[electroph H

Br

CCHCHCHCHCH 2|

23Peroxide

HBr23

C, D 5. Which of the following is correct? a. b. c. d. A, D

Cl2

h

Cl

Cl

Cl

Cl

Cl

Cl

[Free radical Addition]

Ea[1]

Ea[2]

CH3+

(CH3)3C+

C – Cl

Reaction coordinate

En

erg

y Ea[1]

Ea[2] CH3

(CH3)3C+

C – Cl

Reaction coordinate

En

erg

y

Ea[1]

Ea[2]

CH2 = CH

C – Cl

Reaction coordinate

En

erg

y

Ea[1]

Ea[2]

C – Cl

Reaction coordinate

En

erg

y

CH3 – CH – CH3

CH2



SECTION – E (Matrix Type)

This Section contains 3 questions. Each question has four choices (A, B, C and D) given in Column I and five statements (p, q, r, and s) in Column II. (More than one Match may be Answer). No negative Marking 8 × 3 = 24 Marks

1. Match the column – I with column – II.

Column – I Column - II

(A)

(p)

All atoms sp2 hybridised

(B)

(q)

Heterocyclic

(C)

(r)

Antiaromatic

(D)

(s)

Homocyclic

Sol. A p, q; B p, s; C p, q; D p, r, s

2. Match Column – I with Column – II

Column – I Column – II

(A) CH3 – CH2 – O – CH2CH3 and

CH3 – O – CH2 – CH2 – CH3

(p) Tautomers

(B) CH3CHO & CH2 = CH – OH (q) Metamers

(C) CH3COOH and HCOOCH3 (r) Functional Isomers

(D)

(s) Geometrical Isomers

Sol. A Q; B P & R; C R; D S 3. Match Column – I with Column – II

Column – I Column – II

(A)

(p) Most stable conformation

(B)

(q) Least stable conformation

O

NH2

N

CH3

H

C = C

CH3

H

and

CH3

H

C = C

CH3

H

H

H

CH3

CH3

H

H

H

CH3

H H H

H3C



(C)

(r) Gauch conformation

(D)

(s) Partially Eclipsed conformation

Sol. A P; B Q; C P, R; D S

SECTION – F (Integer Type) No Negative Marking

This Section contains 10 questions. The answer to each question is a Single Digit Integer ranging from 0 to 10. The correct digit below the question number in the ORS is to be bubbled.

(10 × 3 = 30 Marks)

1. Total No. of structural isomers possible for formula C4H6. Sol. 9; 1-Butyne; 2-Butyne; buta-1,2-diene; Buta-1,3-diene; Cyclobutene; 2. How many dinitrobenzene can exist. Sol. 3; Ortho; meta and para isomer 3. An alkane has ‘Ethyl’ side chain. What minimum number of carbon should be present in alkane (Do not

consider cyclo-alkane) Sol. 7

4. C2H6

h

Cl2 C2H5Cl, C2H4Cl2, C2H3Cl3, ...... C2Cl6

In total how many structures are possible in products? Sol. 9

)2(

ClCHCHCl

ClHC

CHCCl

22

332

33

)2(

ClCHCHCl

ClHC

ClCHCCl

22

422

23

C2HCl5 CCl3 – CHCl2 (1)

C2Cl6 CCl3 – CCl3 (1)

CH3 – CH2 CH– CH2 – CH3

C2H5

C2H5Cl (1), C2H4Cl2

CH3 – CHCl2

CH2 – CH2

(2)

Cl Cl

CH3

;

CH3

;

CH2

;

H

H

OH

H

H

OH

OH

H H

OH H

H



5. How many primary carbon atoms are present in Isobutane Sol. 3

3

|

|3 CH

CH

H

CCH

3

6. How many of the following compounds will have +M effect

222 HNCHCHCH

; 23 HNCHCHCH

; HOCHCH 23

,

Sol. 4

23 HNCHCHCH

7. Which of the following groups on Benzene ring will make it meta directing:

– C N; ;CH

CH

CH

C 3

|

|

3

3

HO

; 2

||

HN

O

C

; 2HN

; H

O

C||

;

; Cl

O

C||

– Cl;

Sol.6 8. How many of the following will show Geometrical Isomerism.

CH2 = CH2; CH3 – CH = CH – CH3; 3|

CHCH

Cl

CH ;

H

Cl

C

Cl

CH||

; 1,2,-dimethyl cyclopropane; CH3 – CH2 – CH3;

CH3 – CH = CH2

Sol. 4

CH3 – CH = CH – CH3; 3|

CHCHH

Cl

C ; H

Cl

CH

Cl

C||

;

9. How many metamers are possible for formula C4H10O Sol. 3

CH3 – O – CH2 – CH2 – CH3; 3

3

CH

CHCHOCH /

\3 ; CH3 – CH2 – O – CH2 – CH3

10. How many alkyne of formula C5H8 can exist Sol. 3 1-pentyne; 2-pentyne; 3-Methyl-1-butyne

C N;

O – C2H5 ;

Cl ;

O – C – CH3 ;

O

Cl ; O – C2H5 ; O – C – CH3 ;

O

N

O

O

;

C – NH2 ;

O

Cl C

H

Br

CH3 ;

H H

CH3 CH3

CH3

H3C C = C

CH3

CH3

;

Documents

Test Date: 08.02.2015 (Sunday) Time : 11:00 am to 01:00 pm · PDF fileWhich of the following is not an electrophile? a