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13. ORGANIC CHEMISTRY
1. PREVIOUS EAMCET BITS Identify the alkyne in the following sequence of reactions H2 Ozonolysis wac ker Alkyne ⎯⎯⎯⎯⎯ A ⎯⎯⎯⎯ B ←⎯⎯ CH 2 = CH 2 → → ⎯ lindlar 's catalyst process
only

( 2009 E )

1) H 3C − C ≡ C − CH 3 3) H 2 C = CH − C ≡ CH

2) H 3C − CH 2 − C ≡ CH 4) HC ≡ C − CH 2 − C ≡ CH
(A)

Sol:

Ans: 1 Pd / BaSO4 H 3C − C ≡ C − CH 3 + H 2 ⎯⎯⎯⎯⎯⎯ H 3C − CH = CH − CH 3 → Lindlar 's catalysis CH 3 − CH = CH − CH 3 ⎯⎯⎯⎯ CH 3CHO →
Ozonolysis (B)
CuCl2 H 2C = CH 2 + PdCl2 + H 2 O ⎯⎯⎯ CH 3CHO + Pd + 2HCl → H+

(B) Wacker’s process 2. One mole of alkene X on ozonolysis gave one mole of acetaldehyde and one mole of acetone . The IUPAC name of X is ( 2009 E ) 1) 2-methyl-2- butene 2) 2-methyl-l-butene 3) 2 butene 4) 1-butene Ans: 1 Ozonolysis CH 3 − C = CH − CH 3 ⎯⎯⎯⎯ CH 3 − C = O + CH 3CHO → | | CH 3 CH 3 Sol: 2-methyl-2-butene (x) 3. Which one of the following statements is true for the optical rotation exhibited by (2R, 3R) and (2S, 3S) ( 2009 M ) dibromobutene 1) The direction and magnitude are same 2) The direction is opposite but magnitude is same 3) The direction is same but magnitude different 4) Both the direction and magnitude are different Ans: 2 Sol. (2R, 3R) and (2S, 3S) forms are enantiomers of each other. They have equal and opposite optical reactions. 4. Which of the following do not obey Huckel’s rule for Aromaticity ( 2009 M )

I)

II)

III)

IV)

1) all the above 2) I, II 3) III, IV 4) I, IV Ans: 3 Sol: Structure I and II obey Huckels rule III and IV do not obey. 5. Match the following List – I List – II → A) CH 4 ⎯⎯ HCN I) NH , Al O , 1000°C
3 2 3

( 2009 M )

→ B) C2 H 2 ⎯⎯ CH 3CHO → C) C 2 H 4 ⎯⎯ C2 H 2 OH

II) 450°c, heating III) 40% H2SO4, 1% HgSO4, 60°C
1

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Organic Chemistry

D)

C2 H 6 ⎯⎯ C2 H 4 →

IV) con.H2SO4, H2O, 80°C V) Na, dry ether Δ B II I C IV IV D III II

The correct match is A B C D A 1) I III IV II 2) I 3) I IV III II 4) V Ans: 1 1000° C CH 4 + NH 3 ⎯⎯⎯ HCN + 3H 2 → Al2 O3 A −I Sol: A) 1% HgSO4 HC ≡ CH + H 2 O ⎯⎯⎯⎯ CH 3 − CHO → 30% H 2SO 4 B − III B) H 2SO4 H 2 C = CH 2 + H 2 O ⎯⎯⎯⎯ CH 3CH 2 − OH → 75−80%c (C) − IV C) 450° C C 2 H 6 ⎯⎯⎯ CH 2 = CH 2 + H 2 → D) D − II 6. The correct IUPAC name of hydrocarbon X
CH3 CH H 3C CH CH3 CH2 CH3 CH2

( 2009 M )

1) 2-methyl-3-ethyl pentane 2) 3-ethyl-3-methyl pentane 3) 3-isopropyl pentane 4) 1,1-diethyl-2-methyl propane Ans: 1 CH 3 | CH 3 − CH − CH − CH 2 − CH 3 | CH 2 − CH 3 Sol: 2-methyl –3-ethyl pentane 7. The latest IUPAC name f the following compound

( 2009 M)

NH2
1) 2-ethyl-4-bromoaniline 2) 4-bromo-2-ethyl aniline 3) 4-bromo-2-ethyl benzene amine 4) 2-ethyl-4-bromo-benzene amine Ans: 3

C 2H 5

Br

Sol: The latest IUPAC name is 4-bromo-2-ethyl benzene amine

2

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Organic Chemistry

8.

Which of the following compound (S) has Z configuration I) Cl

( 2008 E )

Br II) Cl C C
H F 2) II only C C

F

III) Br

CH3 C C H
4) I and III only

H 1) I only Ans: 4 Sol: I)

Br

Cl

3) III only

Higher atomic number Cl C H Lower atomic number
II)

Higher atomic number Br C F Lower atomic number

Higher atomic number Br C Cl Lower atomic number
9.

Higher atomic number CH3 C H Lower atomic number
( 2008 E )

If higher atomic numbers are same side of the double bond the configuration is Z. What are x and y respectively in the following reaction y X Z product ←⎯ 2 − butyne ⎯⎯ E product ⎯ → 2) Ni/140°C and Pd/BaSO4 + H2 1) Na/ NH3 liq and Pd/BaSO4 + H2 3) Na/ 140°C and Na/NH3(liq) 4) Pd/BaSO4 + H2and Na/NH3 (liq) Ans:1
CH3 Na/Li Liq NH3 H 3C C C CH3 Pd/BaSO4 Lidnlars H CH3 C H C H Z C C CH3 E CH3 H

Sol:

10.

According to Cohn – Ingold- Prelog sequence rules the correct order of priority for the given groups ( 2008 E ) 1) −COOH > −CH 2 OH > −OH > −CHO 2) −COOH > −CHO > −CH 2 OH > −OH 3) −OH > −CH 2 OH > −CHO > −COOH Ans: 4 4) −OH > −COOH > −CH 6 − CH 2 − OH 3

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Sol: According to Cohn – Ingold- Prelog notation system the correct order is −OH > −COOH > −CHO > −CH 2OH CH 3 C2 H 5 − O − CH CH 3 is 11. The IUPAC name of ( 2008 E ) 1) Ethoxy propane 2) 1,1- diethyl ether 3) 2-ethoxy isopropane 4) 2-ethoxy propane Ans: 4 Sol: IUPAC name is 2-ethoxy propane 12. Identify C in the following reaction ( 2008 E) NH3 Δ chromic C 2 H 2 ⎯⎯⎯ A ⎯⎯⎯ B ⎯⎯⎯ C → → → acid H2O
1) CH 3 − CH 2 − NH 2 3) CH 3 − CH 2 − NH − CH 3 Ans: 4 chromic HC ≡ CH + ( O ) + H 2 O ⎯⎯⎯ CH 3COOH → acid Sol:
B (A)

2) CH3 − CN O || CH 3 − C − NH 2 4)

Δ CH 3COOH + NH 3 ⎯⎯ CH 3COONH 4 ⎯⎯⎯ CH 3CONH 2 → → − H2O C

13.

Identify ‘B’ in the following reaction Anhydrous Zn − Cu CH 2 = CH 2 + HCl ⎯⎯⎯⎯ A + 2 [ H ] ⎯⎯⎯⎯ B + HCl → → AlCl3 C2 H5 OH

( 2007 E )

Sol:

1) CH4 2) C2H6 3) C2H5Cl Ans: 2 Anhydrous CH 2 = CH 2 + HCl ⎯⎯⎯⎯ CH 3 − CH 2 − Cl → AlCl3
A

4) C2H5OH

CH 3 − CH 2 − Cl+ 2 [ H ] ⎯⎯⎯→ C2 H 6
A Zn − Cu C2 H 5 O 4

14.

IUPAC names of the compound 1) 5-methyl hex-3-en-2-ol 3) 2-hydroxy-5-methyl-3-hexene
6 5 4 3 2 1

( CH3 )2 CH − CH = CH − CHOH − CH3

B

is 2) 2-methyl hex-3-en-2-ol 4) 5-hydroxy-2-methyl-3- hexene

( 2007 E )

Ans: 1

CH 3 − CH − CH = CH − CH − CH 3 | | CH OH Sol: 5-methyl hex-3-en-2-ol An aqueous solution of an organic compound ‘A’ on electrolysis liberates acetylene and CO2 at anode A ( 2007 E ) is 1) potassium acetate 2) Potassium succinate 3) Potassium citrate 4) Potassium maleate Ans: 4 HC − COOK Electrolysis || + 2H 2 O ⎯⎯⎯⎯ HC ≡ CH + 2CO 2 + 2KOH + H 2 → At anode At cathode CH − COOK Sol: Na / NH3 Lindlars B ←⎯⎯⎯ RC ≡ CR ⎯⎯⎯⎯ A → Catalyst 16. A and B are geometrical isomers then ( 2007 M ) 1) A is cis and B is Trans 2) A is trans and B is cis

15.

4

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3) A and B are cis Ans: 2 Sol: 4) A and Bare trans

R Na/NH3 R C C R H2 Lindars Catalyst H R C H Cis B C C C

H

Trans A R R

H

17.

CH 3 − CH 2 − CH − C = CH 2 | | CH 2 CH 3 | CH 3 is IUPAC name of 1) 2-methyl-3-ethyl-1-pentene 2) 3-methyl-4-methyl-4- pentene 3) 3-ethyl-2-methyl-1 pentene 4) 3-methyl-2-ethyl-1-pentene Ans: 1
5 4 3 2 1

( 2007 M )

CH 3 − CH 2 − CH − C = CH 2 | | CH 2 CH 3 | CH 3 Sol: 3-ethyl-2-methyl-1-pentene 18. Match the following Set – I conc.H 2SO4 C H OH ⎯⎯⎯⎯→ 170° C A) 2 5 Δ CHI3 ⎯⎯⎯⎯ → Ag powder B) electrolysis → C) CH 3COONa ⎯⎯⎯⎯
D) CH3COONa ⎯⎯⎯ →
NaOH CaOΔ

( 2007 M )

Set – II
1) Methane 2) Ethylene 3) Benzene 4) Acetylene 5) Ethane 2) A-2, B-4, C-5, D-3 4) A-4, B-2, C-5, D-3 A–2 B–4 C–5 D–1
5

the correct set is 1) A-2, B-4, C-5, D-1 3) A-4, B-2, C-5, D-1 Ans: 1 conc.H 2SO 4 C H O ⎯⎯⎯⎯→ CH 2 = CH 2 170° C Sol: A) 2 5 17 Δ → B) 2CHI3 + 6Ag ⎯⎯ CH ≡ CH → C) CH 3COONa ⎯⎯⎯⎯ CH 3 − CH 3 NaOH CH 3COONa ⎯⎯⎯ CH 4 → CaO Δ D)
Electrolysis

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Organic Chemistry 1,2-dibromo ethane reacts with alcoholic KOH to yield a product X. The hybridisation state of the carbons present in X, respectively are (2005 M) 3 3 2 2 3 2 1) sp, sp 2) sp , sp 3) sp , sp 4) sp , sp

19.

Ans: 1 H Br | | Alc.KOH Alc.KOH → → H − C − C − H ⎯⎯⎯⎯ H − C = C − H ⎯⎯⎯⎯ HC ≡ CH Acetylene(X) | | | | Br H Br H Sol. In acetylene charbon atom undergoes sp hybridisation 20. The compounds formed at anode in the electrolysis of an aqueous solution of potassium acetate are (2005 M) 1) C2 H 6 and CO2 2) C2 H 4 and CO2 3) CH 4 and H 2 4) CH 4 and CO2 Ans: 1
Elelctrolysis 2CH 3COOK + 2H 2 O ⎯⎯⎯⎯ C 2 H 6 + 2CO 2 + 2KOH + H 2 →

Sol. 21.

Anode

Cathode

C2 H 2 + 2 HCl → C2 H 4Cl2 is an example of ..... reaction (2005 M) 1) Addition 2) Hydrogenation 3) Substitution 4) Chlorination Ans: 1 Cl HC ≡ CH + 2HCl ⎯⎯ CH 3CH → Cl Sol. Unsaturated compounds generally undergo in addition reactions. The above reaction is addition reaction. 22. The chemical and the reaction conditions required for the preparation of ethane are (2004 E) 1) C2 H 5l , Zn − Cu , C2 H 5OH 2) CH 3Cl , Na, H 2O
3) KOOC − CH = CH − COOK , electrolysis 4) CH 3CO2 Na, NaOH , CaO, Δ Ans: 1 Sol. 23.
Zn − Cu / C2 H5 OH C 2 H 5 I + 2 ( H ) ⎯⎯⎯⎯⎯⎯ C 2 H 6 + HI →

alc KOH → The following reaction is an example of - reaction C2 H 4 Br2 ⎯⎯⎯⎯ C2 H 2 1) Addition 2) Dehydrobromination 3) Substitution 4) Debromination Ans: 2

(2004 E)

Sol.
H Br | | Alc.KOH Alc.KOH → → H − C − C − H ⎯⎯⎯⎯ H − C = C − H ⎯⎯⎯⎯ HC ≡ CH − HBr − HBr Acetylene | | | | Br H Br H 24. In the above reaction HBr is eliminated Hence it is a dehydro-bromination reaction. The metal used for the debromination reaction of 1,2-dibromo ethane. (2004 E)

6

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1) Na Ans: 2 2) Zn 3) Mg 4) Li

Alcohol CH 2 − CH 2 + Zn ⎯⎯⎯ H 2 C = CH 2 + ZnBr2 → Δ | | Br Br Sol. ∴ The metal used is Zn 25. What is the molecular formula of the product formed when benzene is reacted with ethyl chloride in presence of anhydrous aluminium chloride? (2004 E) 1) C8 H10 2) C6 H 6 3) C8 H 8 4) C6 H 5Cl Ans: 1 Al.Cl2 → Sol. C6 H 6 + C 2 H 5 Cl ⎯⎯⎯ C6 H 5 − C2 H 5 + HCl

26.

(or) C8H10 Match the following lists. List - I a) ethane b) ethylene c) acetylene d) benzene

(2004 E) List -II 1) two sp carbons 2) six sp2 carbons 3) two sp3 carbons 4) two sp2 carbons 5) one sp and one sp2 carbons

The correct answer is A B C D 1) 3 4 1 2 2) 4 5 3 2 3) 3 1 2 5 4) 2 3 4 5 Ans: 1 Sol. (A) Ethane H 3 C − CH 3 2 sp3 carbons (B) Ethylene H 2 C = CH 2 2 sp2 carbons (C) Acetylene HC ≡ CH 2 sp carbons
CH HC CH

( 2001 )

. (D) Benzene

6sp2 carbons
HC C H CH

27.

The reagent used for converting benzene to ethyl benzene is 1) C2 H 5Cl , anhydrous AlCl3 2) C2 H 5Cl , aqueous AlCl3 3) C2 H 5OH , anhydrous AlCl3 4) C2 H 5Cl , SOCl2 Ans: 1 Anhydrous C6 H 6 + C2 H 5 − Cl ⎯⎯⎯⎯ C6 H5 − C2 H 5 + HCl → AlCl3

(2004 M)

Sol. 28. Which one of the following compounds decolourises cold alkaline potassium permanganate soleuction? (2004 M) 7

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1) C2 H 6 2) C2 H 5Cl 3) C2 H 4 4) C2 H 5OCH 3 Ans: 3 Sol. Unsaturated compounds decolourises cold alkaline potassium permagarate solution 29. Wet ether is not used as a solvent in Wurtz reaction, because the water present in it. (2004 M) 1) hydrolyses RX to ROH 2) reduces RX to RH 3) destroy the Na metal 4) reacts with R-R Ans: 3 Sol. The water vapour in wet ether destroys metal. So wet ether is not used in Wurth reaction 30.
H 2O 80 C → → Δ What are X and Y in the reaction C2 H 4 + H 2 SO4 ⎯⎯⎯ X ⎯⎯⎯ Y 1) C2 H 6 , C2 H 5OH 2) C2 H 4 , C2 H 5 SH
0

(2004 M)

4) C2 H 4 , C2 H 5OH 3) C2 H 5OSO3 H , C2 H 5OH Ans: 3 H 2O 75 −80° c CH 2 = CH 2 + H 2SO 4 ⎯⎯⎯→ CH 3CH 2 OSO3 H ⎯⎯⎯ CH 3 − CH 2 − OH + H 2SO 4 →
(X) (Y) Sol. 31. Which one of the following gases is liberated when ethyl alcohol is heated with methyl magnesium iodide H 2O 800 C C2 H 4 + H 2 SO4 ⎯⎯⎯ X ⎯⎯⎯ → → Δ (2003 E)

Sol. 32.

1) methane 2) ethane 3) propane Ans: 1 Δ C 2 H 5`OH + CH 3MgI ⎯⎯ CH 4 + Mg ( OC 2 H 5 ) I →

4) carbondioxide

∴ The gas liberated is CH4 Wurtz reaction of methyl iodide yields an organic compound X, which one of the following reactions also yields X? (2003 M) dry ether → → 1) C2 H 5Cl + Mg ⎯⎯⎯⎯ 2) C2 H 5Cl + LiAlH 4 ⎯⎯
→ 3) C2 H 5Cl + C2 H 5ONa ⎯⎯ Ans: 2 Ether 2CH 3 I + 2Na ⎯⎯⎯ C2 H 6 →
Ag powder → Δ 4) CHCl3 ⎯⎯⎯⎯

Sol.
LiAlH 4 (X)

(X)

C 2 H 5Cl ⎯⎯⎯ C2 H 6 + HCl → 33. Which one of the following reagents is used for detection of unsaturation in alkenes (2003 M) 2) cold dilute alkaline KMnO4 1) NaOH + CaO

3) Cl2 / hV 4) KOH / C2 H 5OH Ans: 2 Sol. Cold alkaline KMnO4 is used in the detection of alkene and alkynes 34. Which one of the following compounds is prepared in the laboratory from benzene by a substitution reaction? (2003 M) 1) Glyoxal 2) Cyclohexane 3) Acetophenone 4) Hexa bromo cyclo hexane Ans: 3 AlCl3 C6 H 5 − H + CH 3 COCl ⎯⎯⎯ C6 H 5 COCH 3 + HCl → Acetophenone Sol. 8

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35.

C H ⎯⎯⎯⎯⎯⎯→ X ⎯ In the following reaction, 2 2 2) CH 3 − O − CH 3 3) CH 3CH 2 CHO 1) CH 3CH 2 OH
H 2O HgSO 4 / H 2SO 4 ,60° C

Re arrangement

CH 3CHO,

what is X?(2001M) 4) H 2 C = CHOH

CH 3 CHO (X) Sol. 36. ------- test is used for detecting unsaturation in hydrocarbons (2001M) 1) Silver mirror 2) Lassiagne’s 3) Carbylamine 4) Baeyer’s Ans: 4 Sol. Baeyer’s test is used in the detection of unsaturation. 37. Which one of the following is used in the preparation of styrene ? (2001E) 4) C6 H 6 1) CH 3CHO 2) P2 O5 3) CH 4 Ans: 4 Sol. Benzene is used in the preparation of styrene. 38. Which one of the following compound converts methyl magnesium iodide to methane in one step (2002M) 2) C2 H5Cl 3) C2 H 4 4) C2 H5OH 1) C 2 H 5 OC 2 H 5 Sol. 39. When acetylene gas is passed through solution, a white precipitate is formed. 2) ammonical cuprous chloride 1) aqueous AgNO3 Ans: 4 CH 3 MgI + C2 H5 OH ⎯⎯ CH 4 + Mg ( OC2 H 5 ) I →

Ans: 4 H2O HC ≡ CH ⎯⎯⎯⎯⎯⎯→ CH 2 = CH − OH ⎯ HgSO 4 / H 2SO 4 60° C

(2002M)

3) ammonical silver nitrate 4) aqueous potassium permanganate Ans: 3 → Sol. HC ≡ CH + 2AgNO3 + 2NH 4 OH ⎯⎯ Ag − C ≡ C − Ag + 2NH 4 NO3 + 2H 2 O X Y → → 40. In the following reaction X and Y are respectively, C 2 H 2 ⎯⎯ C 6 H 6 ⎯⎯ C6 H 5SO3 H (2002M) 1) ion tube/heating Na 2SO4 2) Zn and conc. H 2SO4 3) red hot iron tube and fuming H 2SO4 4) H 2 / Pd, BaSO4 dil H 2SO4 Ans: 3 Re d hot General C 2 H 2 ⎯⎯⎯→ C6 H 6 ⎯⎯⎯ C6 H 5SO3 H ⎯ → Cu tube heating
A Zn / HCl → In the following reaction A and B respectively are, C 2 H 6 ⎯⎯ C 2 H 5 Cl ⎯⎯⎯→ B PCl3 and C 2 H 4 2) 1) Cl2 /UV light and C 2 H 6

Sol. 41.

(2002M)

B Sol. 42. The reacting ion in the nitration of benzene is (2002M) − − + − 1) NO 2 2) NO 2 3) NO 3 4) O 2 Ans: 2 Sol. Nitration of benzene ring is due to attack of NO2+ ion (nitronium – ion) on the benzene ring.

4) Cl2 and C2 H 2 3) HCl and C 2 H 6 Ans: 1 Cl2 / U.V light Zn / HCl C 2 H 6 ⎯⎯⎯⎯⎯ C 2 H 5 Cl ⎯⎯⎯→ C 2 H 6 → A

9

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43.

→ In the following reaction X and Y are, 2C 2 H 6 + 7O 2 ⎯⎯⎯⎯ X + Y + heat 3) 4CO2 ,10H 2O 4) 4CO2 , 6H 2O 1) 2C2 H 5OH, 6O 2 2) 4HCHO,5H 2O
Combustion

(2002M)

X Y Sol. 44. The reactants and reaction conditions used in the preparation of ethane are C H COOK 1) 2CH 3I, Na / C2 H 5OH 2) electrolysis 2 5 3) C2 H 4 , H 2 , 27°C 4) C2 H 5 I, H 2 , Zn − Cu, C2 H 5OH

ns: 4 Combustion 2C 2 H 6 + 7O 2 ⎯⎯⎯⎯ 4CO 2 + 6H 2 O + heat →

(M2002)

Sol. 45. The reagent used for converting acetylene to oxalic acid is 1) HgSO4 / H 2SO4 2) HgSO 4 / CH 3COOH 3) KMnO4 / KOH Ans: 3

Ans: 4 Zn − Cu C 2 H 5 I + H 2 ⎯⎯⎯⎯ C2 H 6 + HI → C2 H5 OH

(E2002)

4) Cr2 O3 / H 2SO 4

KMnO4 / OH 25° c HC ≡ CH + 4 ( O ) ⎯⎯⎯⎯⎯⎯ COOH → | COOH Sol. 46. The reaction condition used for converting 1,2-dibromo ethane to ethylene are 1) Zn , alcohol, Δ 2) KOH, alcohol , Δ 3) KOH, water, Δ 4) NaCl , alcohol, Δ Ans: 1 Alcohol CH 2 − CH 2 + Zn ⎯⎯⎯ CH 2 = CH 2 → Δ | | Br Br Sol. HBr B ⎯ → 47. In the following reaction, A and B respectively are, A ⎯⎯→ C 2 H 5 Br ⎯⎯ A

(E2002)

(E2002)

1) C2 H 4 and alcoholic KOH / Δ 3) C2 H 5OH and aq KOH / Δ Ans: 1
B

2) C2 H 5Cl and aqueous Br2 / Δ 4) C2 H 2 and Br2

A Sol. 48. The chemicals used for preparing acetophenone are B) CH 3COCH 3 C) CH 3COCl A) C6 H 6

HBr Alcoholic CH 2 = CH 2 ⎯⎯→ C 2 H 5 Br ⎯⎯⎯⎯ CH 2 = CH 2 ⎯ → KOH

(E 2002) D) anhydrous 4) A,B,D

Sol. 49. What is the minimum quantity of methyl iodide required for preparing one mole of ethane by Wurtz reaction (At.wt.of iodine=127) (E2002) 1) 142 gram 2) 568 gram 3) 326 gram 4) 284 gram Ans: 4 → Sol. CH 3 I + +2Na + ICH 3 ⎯⎯ C2 H 6 + 2NaI

1) A,B,C 2) B,C,D 3) A,C,D Ans: 3 Anhydrous C6 H 6 + CH 3 COCl ⎯⎯⎯⎯ C6 H 5 COCH 3 → AlCl3

10

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Organic Chemistry
2 mole of CH3 I is required to prepare 1 mole of ethane. 2 moles of CH3 I = 2(12+ 3x 127) = 284 50. In organic reactions sodium in liquid ammonia is used as (2001 E ) 1) Reducing agent 2) Hydrolysing agent 3) Oxidising agent 4) precipitating agent Ans: 1 Sol: In organic reaction sodium in liquid ammonium used as reducing agent 51. Which one of the following compounds is isomer of 1-butanol (2001 M) 1) 2-methyl-2-butanol 2) 2-methyl-1-butanol 3) 3- methyl -2-butanol 4) 2-methyl-1-propanol Ans: 4 Sol: 1-butanol and 2-methyl -1-propanol are isomers and they have same molecular formula. 52. The structural formula of 2-methyl-2-butene is ( 2001 E) CH 3 − CH ( CH 3 ) − CH = CH 2 CH 3 − CH 2 − C ( CH 3 ) = CH 2 1) 2) CH 3 − CH = C ( CH 3 ) − CH 3 3) CH 3 − CH = CH − CH 3 4) Ans: 4 CH 3 − CH = C − CH 3 | CH 3 Sol: Structure of 2-methyl-2-butene is 53. Which one of the following pairs of compounds are functional isomers ( 2001 E) CH 3CH ( OH ) CH 3 1) CH 3CH 2CH 2OH , CH 3CH 2 CH 2 CH 2 OH, ( CH 3 )2 CHCH 2OH 2) 3) CH 3CH 2 CH 2 OH, CH 3CH 2 CH 2 − Cl

4) CH 3CH 2 CH 2 OH, CH 3OCH 2 CH 3 Ans: 4 Sol: Alcohols and Ethers exhibits functional isomerism and functional isomers have same molecular formula. ( 2001 M) 54. ___ test is used for detecting unsatunation is hydrocarbon 1) Silver mirror 2) Lassaigne’s 3) Carbyl amine 4) Baeyer’s Ans: Sol: Baeyeis test is used in the detection of unsaturated compounds unsalturated compounds decolorises the pink colour of Baeyer is reagent H 2O C 2 H 2 ⎯⎯⎯⎯⎯⎯ X → CH 3CHO HgSO 4 / H 2SO 4 60° c . What is X ( 2001 ) 55. 2) CH 3OCH 3 3) CH 3CH 2 CHO 4) CH 2 = CHOH 1) CH 3CH 2 OH
Vinyl alcohol( X ) Acetaldehyde Sol: 56. Methyl benzene can be prepared by reacting benzene with bromomethane in the presence of 1. AlCl3 2. Br2/ CCl4 3. Ni /H2 4.dil. H2SO4 Ans: 1 AlCl3 → Sol. C6 H 6 + CH 3Br ⎯⎯⎯ C6 H 5CH 3 + HBr

Ans: 4 H2O tautomericm C 2 H 2 ⎯⎯⎯⎯⎯⎯ CH 2 = CH − OH ⎯⎯⎯⎯ CH 3CHO → → HgSO 4 / H 2SO 4 60° c

(2000)

57.

( Friedel craft Alkylation ) Ethylene reacts with Br2 in CCl4 to form x. When x is reacted with alcoholic KOH . Y is formed. Here X and Y are (2000) 2) C2 H 5 Br and C2 H 4 1) BrCH 2 − CH 2 Br and C2 H 2
11

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Organic Chemistry

3) C2 H 5 Br Ans: 1

and

C6 H 6

4) C2 H 3 Br3

and

C2 H 4

Br Br | | CCl4 Alc.KOH CH 2 = CH 2 + Br2 ⎯⎯⎯ CH 2 − CH 2 ⎯⎯⎯⎯ HC ≡ CH → →

Sol.

(X)

(Y)

12

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