test venue: lajpat bhawan, madhya marg ... - chandigarh€¦ · 02/08/2018 · 2 chemistry...

$: Test Venue: Lajpat Bhawan, Madhya Marg ... - Chandigarh€¦ · 02/08/2018 · 2 CHEMISTRY COACHING CIRCLE D:\Important Data\2018\+2\Org\Test\Grand Test\+2 Grand Test-4.doc GRAND$
Dr. Sangeeta Khanna Ph.D 1 CHEMISTRY COACHING CIRCLE D:\Important Data\2018\+2\Org\Test\Grand Test\+2 Grand Test-4.doc

Test Venue:

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

Dr. Sangeeta Khanna Ph.D


GRAND TEST – 4 (Alcohol, Phenol & Grignard Reagent) 25.8.2018

READ THE INSTRUCTIONS CAREFULLY

1. The test is of 1 hour 45 minutes duration. 2. The maximum marks are 262. 3. This test consists of 60 questions. 4. Use of white fluid for correction is NOT permissible on the Answer Sheet

5. Keep your mobiles switched off during Test in the Halls.

Section – A (Single Correct Choice Type) Negative Marking [-1] This Section contains 40 multiple choice questions. Each question has four choices A), B), C) and

D) out of which ONLY ONE is correct. 40 × 4 = 160 Marks

1. Chloroform is more acidic than fluoroform due to

a. Electronegativity of fluorine is more than the chlorine b. Size of chlorine is more than that of fluorine. c. Fluorine is second group element having only s and p-sub-shells whereas chlorine is third group

element having s,p and d-sub-shell in which d sub-shell is empty.

d. 3

Θ

FC is less stable than 3

Θ

ClC due to the vacant d-orbital of chlorine.

D 2. Consider the following reaction:

)B(

||

3)A(23 OH

O

CCHHOCHCH . HOHCH

O

COCHCH 3

||

23

In the above reaction ester formation takes place by:

a. Breaking of O – H bond of (A) & O – H bond of (B) b. Breaking of C – O bond of (A) & C – O bond of (B) c. Breaking of O – H bond of (A) & C – O bond of (B) d. Breaking of C – O bond of (A) & O – H bond of (B)

C

3. An unknown organic compound [X] on treatment with K2Cr2O7/H gives another unknown compound Y

which has only C’s. H’s & oxygen. Compound Y reacts with I2/Na2CO3 to form CHI3. The compound [X] is:

a. CH3OH b. CH3COCH3 c. CH3 – CHO d. CH3 – CHOH –CH3 D

Sol. Alcohol Methylketone

A B

4. List I List II I. Wurtz reaction

II. Hydration of alkenes

III. Nitration of benzene

IV. Hydration of alkynes in presence of Hg+2

i. Electrophilic substitution reaction

ii. Nucleophilic addition reaction

iii. Electrophilic addition reaction

iv. Free radical reaction

I II III IV I II III IV I II III IV I II III IV

a. (ii) (iii) (iv) (i) b. (iv) (iii) (ii) (i) c. (iv) (iii) (i) (ii) d. (i) (iii) (ii) (iv) C

Sol. Addition reactions of alkynes in presence of Lewis acid are nucleophilic addition



5. Which of the following reactions would give the best yield of t-butyl methyl ether?

a. (CH3)3C – OH C140

4SO2H

b. (CH3)3C – Br + CH3OH

c. (CH3)3C – Br + CH3NaO

Θ

d. BrCHKOC)CH( 3

Θ

33

D

6. Product P is a. 2, 4, 6-Tribromophenol b. 3, 5-dibromo-2-hydroxy benzoic acid

c. dibromosalicylic acid d. Monobromosalicylic acid A

7. Conversion of I to II : a. takes place by SN1 b. takes place by SN2 c. takes place by SN d. does not take place D 8. Which of the following is not expected to be intermediate of the following reaction? a. b. c. d. A 9. The following compound ‘X’ can exist in how many orientation?

3

2 3

3

|

| |

CHCH CH/

H C C C\CH

HHO

a. 1 b. 2 c. 3 d. 4 D

COOH

Br2 – water P

OH

Br

H

OH–

H

(I) (II)

OH

I H2O

OH

CH3

CH2

CH3

CH3

OH2

H3C



10. Find the product in the given reaction

3

3

2 2

| 1. BH

3 22. H O , OH

CH

CH CH CH CH

a.

3| |

3 3

CH OH

CH CH CH CH b.

3|

3 2 2|

CH

CH CH CH CH

OH

c.

3

|

3 3|

OH

CH CH CH CH

CH

d.

3|

3 2

CH

CH CH CH CHO

B 11. Major product A is a. b. c. d. C Sol. ring fusion 12. The major product formed by the action of NaBr/H2SO4 on neo pentyl alcohol is, a. neo pentyl bromide b. 2-bromo 2-methyl butane c. n-pentyl bromide d. 2-bromo 3-methyl butane B

Sol. CC

C

Br

CCCHCH

CH

CCHCH

CH

CH

CCHOHCH

CH

CH

CCH|

|

Br32

|

3shif t Methy l

2

|

|3

H2

|

|3

33

3

3

3

13. Which of the statements is incorrect?

a. 2,4,6-trimethyl phenol is less acidic than 2,4,6-trinitrophenol b. 2,6-dichlorophenol is stronger than 3,5 dichloro phenol c. para nitro phenol is more acidic than meta nitro phenol d. para chloro phenol is less acidic than para flouro phenol. D

Sol. para chloro phenol more acidic then para fluoro phenol since para chloro phenoxide has larger number of resonance stabilised structures due to presence of d-orbital.

14.

Identify B in the sequence a. Methyl orange b. Phenolphtheline c. Aspirin d. Methyl blue C

Sol. Kolbe’s reaction forward by acylation

H2SO4

OH

(A) (Major)

O–Na

+

CO2

A

Ac2O

H3PO4 B



15. In the above transformation ‘X’ could be

a. NaBH4|C2H5OH|H3O+ b. N2H4|OH–|Glycol|

c. LiAlH4|Et2O|H3O+ d. DIBAL-H|THF|H3O

+ C Sol. Only LiAlH4 reduces COOH group.

16. The above transformation can be done by using

a. Baeyer’s Reagent b. Tollen’s reagent c. Pyridinium dichlormate in CH2Cl2 d. Jone’s reagent C,D

17. Which of the following alcohols would be most likely to undergo dehydration with rearrangement by a process involving a methyl migration (methyl shift)?

a. b. c. d. A

18. Rank the following alcohols in order of decreasing reactivity (fastest slowest) toward dehydration with 85% H3PO4:

3

HCH

OH

CCH)(CH

2

CHCH

OH

C)(CH

1

OHCHCHCH)CH( 3

|

2332

|

232223

a. 2 > 3 > 1 b. 1 > 3 > 2 c. 2 > 1 > 3 d. 1 > 2 > 3 A 19. A certain alcohol has the functional class IUPAC name 1–ethyl-3-methylbutyl alcohol. What is its

correct IUPAC name?

a. 1 – Ethyl – 3 – methyl – 1 butanol b. 2 – Methyl – 1 – hexanol c. 3 – Methyl – 1 – hexanol d. 5 – Methyl – 3 – hexanol

D

Sol. 52

3

HC

OH/\

CC

CH

CC|

20. The order of reactivity of methyl alcohol (I), isopropyl alcohol (II) tertiary butyl alcohol (III) and ethyl alcohol (IV) for esterification in decreasing order will be:

a. I > II > III > IV b. IV > III > II > I c. I > IV > II> III d. I > IV > III > II C 21. A compound A of formula C3H6Cl2 on reaction with alkali can give B of formula C3H6O or C of formula

C3H4. B on oxidation gave a compound of the formula C3H6O2. C with dilute H2SO4 containing Hg2+ ion gave D of formula C3H6O, which with bromine and alkali gave the sodium salt of C2H4O2. Then A is:

a. CH3CH2CHCl2 b. CH3CCl2CH3 c. CH2ClCH2CH2Cl d. CH3CHClCH2Cl A

OH

OH OH OH

O

O

OH X

HO

OH

H3C

HO

OH

H3C

O

H

O



22. Sodium metal is added to t-butyl alcohol. When the metal was consumed, ethyl bromide is added to the reaction mixture. The end product is an …..

a. acid b. alcohol c. ether d. aldehyde C

Sol. 52

3

3

|

|3

NaBr

Br5H2C

3

3

|

|3

2H21

Na

3

3

|

|3 HCO

CH

CH

CCHONa

CH

CH

CCHOH

CH

CH

CCH

(Williamson synthesis)

23. In the following compounds, The order of acidity is a. III > IV > I > II b. I > IV > III > II c. II > I > III > IV d. IV > III > I > II D 24. Given A = , B = , C = , D = The decreasing order of their acid character is a. A > B > C > D b. B > A > C > D c. B > D > C > A d. C > B > A > D C 25. The IUPAC name of

3

|

2|

2|

3 CHH

OH

CH

SH

CH

NH

CCH

a. 4-Hydroxypentan-2-amine b. 4-Hydroxy-2-aminopentane thiol c. 2-Amino-3-mercapto-pentan-4-ol d. 4-Amino-3-mercaptopentan-2-ol D 26. Among the following compounds, the strongest acid is:

(a) HC CH b. C6H6 c. C2H6 d. CH3OH D

Sol. HOCH OHCHΘ

33

Since, -ve charge is on electronegative oxygen. So, CH3OH is most acidic. 27. Consider the following benzyl alcohol:

OH

Cl

OH

OMe

OH

NO2

OH

CH2OH

(I)

CH2OH

(II)

NO2

CH2OH

(III)

OCH3

CH2OH

(IV)

Cl

OH

(I)

OH

(II)

CH3 OH

(III)

NO2

OH

(IV)

O2N



Correct order of their Kb value is: a. III > IV > II > I b. III > I > IV > II c. I < II < III < IV d. IV > II > I > III B 28. Correct stability order is a. P > R > Q > S b. Q > R > S > P c. R > S > Q > P d. P > R > S > Q A 29. Which of the following pairs of compounds are not isomers? a. b. c. d. C,D 30. The major products P and Q are: a. b. c. d.

C Sol.

CH2

OH

(P)

CH2

(Q)

CH2

NH C CH3

(R)

O

CH2

NO2

(S)

OH

CH3

and

OH

CH3 H3C OH

and

CH3

OH

CH2OH

and

CH3

CH3

OH

and

CH3 HO

and CH3 – CH2 – CHO

and CH3COCH3

and CH3COCH3 and CH3 – CH2 – CHO

+ Cl – CH2 – CH2 – CH3 AlCl3

P (i) O2/

(i) H3O+

Q + Phenol

Cl – CH2 – CH2 – CH3 AlCl3

– AlCl4–

CH2 – CH2 – CH3

CH3 – CH – CH3

/AlCl4–

O2

CH3 – C – O – OH

CH3

H+/

C

CH3 CH3

O

C

CH3

H

CH3

(P)

+ AlCl3 + HCl +

OH



31. Which of the following alcohols will not react with Cu/?

a. CH3 – CH2 – OH b. OH

Ph

Ph

CPh|

| c. OH

CH

CH

CCH

3

3

|

|3 d.

OH

CHCHPh

3

/\

B 32. Which of the following alcohols would be most reactive with a Grignard reagent?

a. CH3OH b. (CH3)3COH c. CH3CHOHCH3 d. CH3(CH2)11CH2OH A

Sol. Methyl alcohol is the strongest acid and will thus react most vigorously with a Grignard reagent. The strongest acid is the primary alcohol with the shortest carbon chain.

33. Which of the following is correctly matched a. tert pentyl alcohol – 1,1-Dimethylpropan-1-ol b. neopentyl alcohol – 2,2-Dimethylpropan-1-ol c. sec.-butyl alcohol – 1-Methylpropan-2-ol d. Anisol – Methyl benzene B

34. What are x, y & z in the following conversion. x y z

a.

b. c. d. A

OH

(1) CCl4 + NaOH

(2) H3O+

x Br2/water

y Zn/dust

z

OH

COOH

OH

Br

Br Br

Br

Br Br

OH

COOH

OH

Br

Br Br COOH Br

Br

OH

CHO OH

Br

Br Br Br

Br

Br

OH

COOH

OH

Br

Br

Br

Br

Br

OH



35. Which of the following reagent cannot be used to distinguish ethanol and phenol

a. Iodoform test b. Br2-water Test c. FeCl3-test d. NaHCO3 test D

Sol. Both phenol & alcohol donot react with NaHCO3

36. 2 3

3

Cl /FeCl1. NaOH

2. NaOCHA B C

A, B & c are respectively a. b. c. d.

D 37. Predict the product when given compound reacts with LiAlH4. a. b.

;

Cl

; CH3OH

SO3Na

;

OCH3

;

OCH3

Cl

OCH3

;

OCH3

Cl ;

OCH3

Cl

OCH3

;

OCH3

Cl

;

OCH3

Cl

SO3H

C–O–CH3

O

OH C–O–CH3

O

OH

OH

OCH3 C

O

C

O

H

O



c. d. C

38. For the given reaction Θ||Θ||

LNu

O

CRuNL

O

CR

which of the following species is formed as an intermediate ?

a. R – C

O b. R-

C = O c. L

O

Nu

CR

Θ

|

| d. uN

….

O

R

C| |

|….

L

C Sol. This Reaction involve formation of tetrahedral Intermediate 39. In the following sequence of reactions,

3

2

|3 CHH

NH

CCH BAOxidation(aq.) HNO2

O2H/H)ii(

MgI3CH )i(

C

the compound C formed will be: a. Butanol – 1 b. Butanol – 2 c. 2 Methylpropanol – 1 d. 2 – Methyl propanol – 2 D

Sol.

3|

(O)3 3 3 3 3 3

| || |

(A) (B) (C)

CH

CH CH CH CH C CH CH C CH

OH O OH

40. a. b. c. d.

B

OH

OH

OH

OH

OH C

O

H

O

O

CH3

CH3

CH3 OH H

CrO3Cl

dichloro methane (A)

N



SECTION – C (Paragraph Type) Negative marking [-1] This Section contains 2 Comprehension. Each of these questions has four choices A), B), C) and D)

out of which ONLY ONE is correct. 7 × 4 = 28 Marks

Comprehension –1 Use the table of physical constants below answer questions Alcohol Molecular Weight Boiling Point benzyl alcohol 108.14 205°C cyclohexyl alcohol 100.16 161°C isoamyl alcohol 88.15 130°C octyl alcohol 130.23 196°C propyl alcohol 60.10 82°C

1. If a mixture of the alcohols shown in the table is distilled, which alcohol would be the last to come

across?

a. benzyl alcohol b. isoamyl alcohol c. octyl alcohol d. propyl alcohol A

Sol. Benzyl alcohol has the highest boiling point, so it will be the last to come across in distillation. 2. Which of the following mixtures would be the easiest to separate using distillation?

a. benzyl alcohol and propyl alcohol b. isoamyl alcohol and propyl alcohol c. benzyl alcohol and octyl alcohol d. octyl alcohcol and cyclohexyl alcohol A

Sol. Benzyl and propyl alcohols have the largest difference in boiling point, therefore they are the easiest to separate using distillation

3. Benzyl acetate (boiling point 206 °C) is synthesized by reacting acetic anhydride with benzyl alcohol. What is true about the distillation to separate the ester from the alcohol starting material?

a. The ester and alcohol will come across as pure vapour b. The distillation cannot be carried out with a simple distillation apparatus c. The benzyl acetate will come across first d. The distillation will be fast. B

Sol. The two have boiling points that differ by 1°C so they cannot the separated by distillation. 4. Which of the following will have lowest Boiling point?

a. CH3 – O – CH3 b. CH3CH2OH c. CH3CH2 – CH3 d. 3

O||

3 CHCCH

C

Comprehension – 2 Grignard reagents resemble carbanion hence they act as strong nuclephiles as well as strong bases. They give nucleophilic addition reactions with compounds containing hetero multiple bonds such as carbonyl compounds. The addition products on hydrolysis give alcohols. The readily take part in acid-base reactions with compounds containing acidic hydrogens.

5. Which of the following compound will not give acid-base reaction with RMgX? a. CH3 – CH2 – CN b. CH3 – CO – CH2 – CO – CH3 c. CH3 – NO2 d. CH3OH A

Sol. Cyanides give nucleophilic addition with Grignard reagents. The other compounds contain more acidic hydrogen.

RMgX +

Θ

O R O Θ

MgX

H2O R OH + Mg(OH)X



6. Which of the following compounds give racemic mixture on reaction with methyl magnesium bromide? a. HCHO b. CH3 – CO – CH3 c. Ph – CHO d. CH3 – COCl C

Sol. Only benzaldehyde gives optically active products. 7. Arrange the following compounds in decreasing order of nucleophilic addition reaction?

(P) CH3 – CHO (Q) CH3 – CO – CH3 (R) COCl2 (S) Ph – CHO a. R >P > S > Q b. P > Q > R > S c. Q > R > S > P d. R > S > P > Q A

Sol. Reactivity is proportional to the electrophilicity of the carbonyl carbon.

SECTION – D (One or More than One Answer) No Negative Marking

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 × 5 = 25 Marks

1.

(X) The product P

a. is the retended form of (X) b. is the inverted form of (X) c. has no chiral carbon d. is a meso compound B

Sol.

2. Grignard reagent is not prepared in aqueous medium but prepared in ether medium because

a. the reagent is solvated in ether b. it is insoluble in water c. the reagent becomes inactive in water d. the reagent reacts with water A, D

Sol. The reagent reacts with H2O

RMgX + H2O RH + Mg(OH)X 3. Which of the following will give CH4 with CH3MgBr.

a. CH3NH2 b. CH3SH c. HC CH d.

3

3|

CH CH OH

CH

A,B,C,D 4. Which of the following compounds would yield chloroform on warming with bleaching powder paste?

a. 1-Propanol b. Propanone c. Ethanol d. Propanol B,C

Sol. For haloform reaction, the compound should have group

OH

CCH or

O

CCH|

3

||

3

H OTs

D

CH3

(1)

CH3COO

CH3

D

H

(2)

CH3C – OH

(3) & (4)

O

18 +

CH3

D

H HO

(P)

H OH

D

CH3

(1) (2)

CH3COONa 18

OH/H2O (Ester hydrolysis) Acidification CH3COOH + (P)

(3) (4)

18

Me Cl S

O

O



5. In the given reaction

[Y] ]X[BrCHCHCHHCHOH

256

[X] and [Y] are a. b. c. d. A,B

Sol. Ph – CH = CH – CH2 – Br Ph – CH = CH – 2CH CC

OH

CPhCHCHHCPh|

SECTION – E (Matrix Type) No Negative Marking

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. Any given statement in Column I can have correct matching with one or more statement(s) given in Column II. 8 × 3 = 24 Marks

1. Match the Column – I with Column – II (One or More than One Match) Column – I Column – II

(A) (p) Electrophilic substitution reaction (B) (q) Nucleophilic substitution reaction

(C) OHCHI

CH

CH

CCHCHO

CH

CH

CCH 3

|

|3

HI3

|

|3

3

3

3

3

(r) Elimination

(D) 3

|

3SOH

32

|

|3 CHCH

CH

CCHCHCH

CH

OH

CCH

3

42

3

(s) Coupling

Sol. A p, s; B q ; C q ; D r 2. Match the Column – I with Column – I (One or More than One Match)

Column - I Column-II (A)

(p)

(B)

(q)

HO + Cl – N2

0 – 50C

HO N = N

N2Cl H2O

600C OH

CH3

CH3

OH

POCl3

Pyridine

CH3

CH3

CH3

CH3

OH

Conc. H2SO4

CH3

CH3

H5C6 OH

CH2

H5C6

OH

CH2

H5C6

OH



(C)

(r)

(D)

(s)

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

(A) E2 Elimination

(B) E1 Elimination (C) (D) Williamson’s synthesis (SN2)

3. Match the column (I) and (II). (Single Match)

Column – I (Reaction) Column – II No. of moles of CH3MgCl Reacted

(A)

(p)

4

CH3

CH3

OH

CH3

CH3

OH

NaOH

C2H5Br

CH3

CH3

Cl

CH3

CH3

OC2H5

CH3

CH3

O – H

O = P

Cl

Cl

Cl

CH3

CH3

OPOCl2

H

E2

CH3

CH3

Pyridine

CH3

CH3

OH

H+

CH3

CH3

OH2 –H2O

CH3

CH3

2°Carbocation

CH3

CH3

Methyl

Shift

–H+ CH3

CH3

CH3

CH3

OH

SOCl2

SN2

CH3

CH3

Cl

CH3

CH3

OH

NaOH

CH3

CH3

ONa

SN2

C2H5Br

CH3

CH3

OC2H5

SOCl2

Pyridine

HO O O

(i) CH3MgBr

(ii) H3O+

HO OH

HO SH

OH

SH

OH



(B)

(q)

3

(C)

3

|

|

|

|3

OH)2

MgClCH)1||||

CH

OH

CH

C

OH

CH

CCHOEt

O

C

O

CEtO

33

3

3

(r)

2

(D)

3

|

|

|

|3

OH)2

MgClCH)1||||

3 CH

OH

CH

C

OH

CH

CCHCl

O

C

O

CCH

33

3

3

(s)

5

Sol. A s; B r; C p; D q (A) one CH3MgCl reacts with phenolic –OH and other two reacts with cyclic ester group to produced alcohol.

SECTION – F (Integer Type) No Negative Marking

This Section contains 5 questions. The answer to each question can be between from 0 to 100.

5 × 5 = 25 Marks

1. Total number of stable isomers of molecular formula C3H8O2 [only alcohol & ether] Sol. 8 Alcohols Ethers

(i) 2|

22|

H

OH

CCHH

OH

C (i) CH3 – O – CH2 – CH2OH

(ii) )(

(-) H

OH

CH

OH

CCH 2||

3

(ii) )(

)( CHH

OH

COCH 3|

3

(iii) CH3O – CH2 – OCH3

gem diols are not stable 2. If the I.U.P.A.C name of compound is as

3

3 3|

CH C C CH CH

OCH

m-Methoxy-n-pentyne then what is m

n

Sol. 2

4-Methoxy-2-pentyne so m 4

2n 2

O

COCH3

1) CH3MgCl

2) H3O+

CH3 HO

C CH3 HO

CH3

COCH3 O (B)

(C) Et – O C

O

C

O

O – Et (D) C

O

CH3 COCl

HO O O

SH

OH

(A)



3. How many of the following would produce a distinct coloration with Victor Meyer test?

a. b. CH3CH2OH c. d. e. f. g. h. i. Sol. 5 (Pri. & sec.) (a, b, c, e, f) 4. How many of the following are weaker acids than H2CO3.

(6) CH3CH2SH; (7) C6H5SH; (8) CH3COOH; (9) CH3SO3H

Sol. 6 [1, 3, 4, 5, 6, 7] 5. A compound of formula C4H10O4 (A) on acetylation give a product with formula C12H18O8 (B) Number of

-OH groups in compound (A) is Sol. 4

OH

OH

OH

OH

OH

OH

OH OH

OH

OH

OH

(1) ;

OH

(2) ;

NO2

NO2

OH

(3)

NO2

;

OH

(4)

CH3

;

OH

(5)

OCH3

;

CH2OH

CHOH

CHOH

CH2OH

HCH3COCl

CH2 – O – C – CH3

O

CH – O – C – CH3

CH – O – C – CH3

O

O

CH2 – O – C – CH3

O

C4H10O4 [C12H18O8]

test venue: lajpat bhawan, madhya marg ... - chandigarh€¦ · 02/08/2018 · 2 chemistry...

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