ORGANIC CHEMISTRY –II

ALCOHOLS ETHERS AND PHENOLS
PREVIOUS EAMCET BITS 1. What are the X and Y in the following reaction sequence? Cl2 Cl2 C2 H 5OH ⎯⎯ X ⎯⎯ Y → → 1) C2 H 5Cl , CH 3CHO 2) CH 3CHO, CH 3COOH 3) CH 3CHO, CCl3CHO 4) C2 H 5Cl , CCl3CHO (2009 E)

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Ans : 3 Cl2 Cl2 Sol: C2 H 5 − OH ⎯⎯ CH 3CHO ⎯⎯ CCl3CHO → → (X) 2. (Y)

What is the hybridisation state (s) of the atoms in X formed in the following reaction Al2O3 C2 H 5OH ⎯⎯⎯ X → 2600 C (Vapours) 1) Sp3 only 2) Sp only Sp
2 3

3) Sp only

2

(2009 M) 4) Sp only

Ans : 1 Al2O3 Sol: 2C2 H 5OH ⎯⎯⎯ C2 H 5 − O − C2 H 5 → 2600 C (X) Atoms have Sp hybridisation
3

3.

In which of the following reaction chlorine acts as an oxidizing agent i) CH 3CH 2OH + Cl2 → CH 3CHO + HCl ii) CH 3CHO + Cl2 → CCl3CHO + HCl iii) CH 4 + Cl2 → CH 3Cl + HCl The correct answer is 1) i only 2) ii only 3) i and iii

(2008 E)

4) i, ii and iii

Ans : 4 Sol:
Oxi (i) C2 H 6 O ⎯⎯→ C2 H 4 O2 Oxi → (ii) C2 H 4 O ⎯⎯ C2 Cl3 H O Oxi (iii) C H 4 ⎯⎯→ C H 3 Cl −4 +1 −2 +1 −1 −1 +1 −2 +2 −1 +1 − 2 −2 +1 −2 0 +1 −2

4.

Identify A and B in the following reaction B A CH 3CH 3 ←⎯ CH 3COOH ⎯⎯ CH 3CH 2OH ⎯ → A 1) HI + Red P 2) NI/ Δ 3) LiAlH4 4) Pd – BaSO4 B LiAlH4 LiAlH4 HI + Red P Zn + HCl

(2008 E)

Ans : 3 LiAlH 4 Sol: CH 3COOH ⎯⎯⎯ CH 3CH 2OH →
HI + Re d P CH 3COOH ⎯⎯⎯⎯ CH 3 − CH 3 →

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A → LiAlH 4
5.

Powered by myengg.com B → HI + Re d P

Organic Chemistry – II

Pyrodine C2 H 5OH + SOCl2 ⎯⎯⎯⎯ X + Y + Z →

In this reaction X, Y and Z respectively are 1) C2 H 4Cl2 , SO2 , HCl 2) C2 H 5Cl , SO2 , HCl 3) C2 H 5Cl , SO Cl , HCl 4) C2 H 4 , SO2 , Cl2 Ans : 2 Sol: C2 H 5Cl + SOCl2 → C2 H 5Cl + SO2 + HCl X 6. Y Z

(2008 M)

Methyl alcohol when reacted with carbon monoxide using cobalt (or) Rhodium as catalyst, compound A is formed, A on heating with HI in the presence of red phosphorous as catalyst B is formed identify B (2007 M) 1) CH3COOH 2) CH3CHO 3) CH3CH2I 4) CH3- CH3

Ans : 4 Cobalt ( or ) Rhodium Sol: CH 3OH + CO ⎯⎯⎯⎯⎯⎯ CH 3COOH → (A)

CH 3COOH ⎯⎯⎯⎯ CH 3 − CH 3 →
(A) 7. B

HI + Re d P

Which of the following compounds when heated with CO at 1500C and 500 atm pressure in the presence of BF3 form ethyl propionate (2006 E) 1) C2H5OH 2) CH3OCH3 3) C2H5OC2H5 4) CH3OC2H5

Ans : 3 BF3 /1500 C Sol: C2 H 5OC2 H 5 + CO + ⎯⎯⎯⎯ C2 H 5COOC2 H 5 → 500 atm 8. In which of the following reaction ethylene is formed (2006 M) 0 0 2) CH3OH, con H2So4, 170 C 1) C2H5OH, dil H2So4, 0 C 3) C2H5Br, Zn, Δ 4) C2H5OH, con H2So4, 1700C

Ans : 4 con H 2 SO4 /1700 C Sol: CH 3CH 2OH ⎯⎯⎯⎯⎯⎯ CH 2 = CH 2 + H 2O → 9.
Cu → In the reaction C2 H 5OH ⎯⎯⎯ X 3000 C

(2005 E)

(Vapour) The molecular formula of X is 1) C4H6O 2) C4H10O Ans : 3 Cu Sol: C2 H 5OH ⎯⎯⎯ CH 3CHO + H 2 → 3000 C (or) C2H4O 10.

3) C2H4O

4) C2H6

A B → ⎯ Identify A and B in the following reaction C2 H 5Cl ⎯⎯ C2 H 3OH ←⎯ C2 H 5Cl

(2004 E) 1) A = aqueous KOH B = AgOH 2) A = alcoholic KOH B= aqueous NaOH Powered by 2 myengg.com

Powered by myengg.com 3) A = aqueous NaOH B = AgNO2 4) A = AgNO2 B=KNO2 Ans : 1 Aq KOH Ag OH Sol: C2 H 5Cl ⎯⎯⎯→ C2 H 5OH ←⎯⎯ C2 H 5Cl ⎯ ⎯ A 11. What are X and Y in the reaction H 2O 800 C C2 H 4 + H 2 SO4 ⎯⎯⎯ X ⎯⎯⎯ Y → → Δ 1) C2H5, C2H5OH 3) C2H5, OSO3H, C2H5OH Ans : 3 800 C Sol: CH 2 = CH 2 + H 2 SO4 ⎯⎯⎯ CH 3CH 2 HSO4 → (X) CH 3CH 2 HSO4 + H 2O ⎯⎯ CH 3CH 2OH + H 2 SO4 → (Y) 12.
BF3 In the reaction C2 H 5OC2 H 5 + CO ⎯⎯⎯⎯⎯ X → 1500 C , 500 atom

Organic Chemistry – II

(2004 E) 2) C2H4, C2H5OH 4) C2H2, CH3CHO

(2003 E)

1) Diethyl carbonate 3) Diethyl peroxide

2) Ethyl carbonate 4) Ethyl propionate

Ans : 4 BF3 /1500 c Sol: C2 H 5 − O − C2 H 5 + CO ⎯⎯⎯⎯ C2 H 5COOC2 H 5 Ethyl propionate. → 500 atm 13. Canned heat is prepared by mixing -------------- and ------------- at high pressure (2003 M) 1) C2H5OH, HI/ Red P 2) C2H2, O2 3) C2H5OH, Ca(OH)2 4) C3H6O, CaOCl2

Ans : 3 Sol: Ethyl alcohol is mixed with saturated solution of calcium hydroxide to give a solid gel canned heat. 14. The products formed when diethyl ether is reacted with cold HI are 1) C2H5I + C2H5OH 2) 2C2H5I + H2O 3) 2C2H5OH 4) C2H5-O-O-C2H5 +H2O (2002 E)

Ans : 1 cold Sol: C2 H 5 − O − C2 H 5 + HI ⎯⎯⎯ C2 H 5OH + C2 H 5 I → 15. Which one of the following compounds converts methyl magnesium Iodide to methane in one step (2002 M) 1) C2H5OC2H5 2) C2H5Cl 3) C2H4 4) C2H5OH

Ans : 4 CH 3 MgI + C2 H 5OH → CH 4 + Mg Sol:

OC2 H 5

16.

I Chloro ethane reacts with X to form diethyl ether. What is X 1) NaOH 2) H2SO4 3) C2H5ONa

(2001 E) 4) Na2S2O3

Ans : 3 Sol: C2 H 5Cl + NaOC2 H 5 → C2 H 5OC2 H 5 + NaCl Powered by 3 myengg.com

Powered by myengg.com 17. Williamson’s synthesis is used for preparing 1) Alcohols 2) Ketones 3) Ethers

Organic Chemistry – II (2001 M) 4) Aldehydes

Ans : 3 Sol: Williamson’s synthesis Δ C2 H 5ONa + IC2 H 5 ⎯⎯ C2 H 5 − O − C2 H 5 + NaI → 18. Which of the following reacts with ethanol to form chloroform 1) SOCl2 2) PCl3 3) HCl (2000 E) 4) CaOCl2 / H2O

Ans : 4 H 2O Sol: C2 H 5OH + CaoCl2 ⎯⎯⎯ CHCl3 + ( HCOO )2 Ca → 19. Which of the following is Lucas reagent 1) Ammonical silver nitrate 3) ZnCl2/con HCl (2000 E) 2) Br2/CCl4 4) Cold Alkaline KMnO4

Ans : 3 Sol: ZnCl2/con HCl is called Lucas reagent. 20. Which of the following conditions are used for the conversion of ethanol to ethylene (2000 E) 0 0 1) Con H2SO4 / 70 C 2) dil H2SO4 / 140 C 0 3) dil H2SO4 / 100 C 4) Con H2SO4 / 1700C Ans : 4 160 −1700 C Sol: C2 H 5OH + Con H 2 SO4 ⎯⎯⎯⎯ CH 2 = CH 2 + H 2O →

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