Chem Jee Soln Set

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1 (a) Lucas rcagcnt is conc. HCl+ anhyd. ZnCl,.

2 (c) Step 2: (CH,),C -0H,: (CH),c + H,0


3. (a) Methyl alcohol (CH,0H) is also known as carbinol. Hence 3° Carbocation
vinyl carbinol is CH, =CH-CH,OH
4. (a) 3-methyl pentanol-3 willbe dehydrated most readily Step 3: (CH}); C* +CI(CH,),C -CI
since it produces tertiary carbonium ion as intermediate. t-Butylchlornde
10. (d) The two components should be (CH),CONa +
CH, (CH),(Br. However, tert-alkyl halides tend to undergo
climination rcaction rather than substitution kcading to
CHy -CH, - -CH, -CH, the formation ofan alkene, Me,C= CH,
OH 11. (d)
12. (d)
distill
(C,H,0), Mg+ H,0- ’2C,H,OH+ Mg(OH);
H,CH; -CH, -C -CH, -CH; (distillate ) (residue j
13. (a) MnO, being a mild oxidising agent stops the
5. (C) oxidation of - CH,OH group at aldehyde stage.
14. () The tertiary alky halide undergo elimination reaction
6. (c) CH,CHCHl to give alkenes

7. (d) 2-Phenylethanol, CGHsCH,CH,OH, is a | alonhal CH;


which can be prepared from C,,HMgBr by treating with
ethylene oxide(note that HCHO will introduce only one CH -x +NaC,H’
carbon atom, i.e. it will give C,H,CH,0H and not
CH3
C,H,CH,CH,OH).
CGH,MgBr+ CGHsCH,CH,0H: CH:
C,H,MgBr +HCHO C,H,CH,OH
CHC=CH)
(b) Methyl vinyl ether under anhydrous condition at ronm 2-methyl propene
iemperature undergoes addition reaction.
HRr
OH OH OH
CH= CH-OCH; ’CH; -CH-0-CH, COOH
CH,
Br 15. (d)
9 (b) Tertiary alcohols react fastest with conc. HCI and 0-cresol Salicylic acid Phenol
anhydrous ZnCl, (lucas reagent) as its mechanism
proceeds through the formation of stable tertiary Electron releasing groups(-CH¡, -0CH,-NCH, etc)
carbocation. intensify the negative charge of phenoxide ion, i.e.,
Mechanism destablises it hence decrease ionization of parent
phenol. Therefore decreases acidity while electron
donating groups(-N0,,-COOH,-CHOetc.)increases
ÇH, acidity.
Sep I: CH,C -OH+ H-CI 16. (b) Number ofactive hydrogen in a compound corresponds
to the number of moles of CII, evolved per mole of the
CH, Compound.
2 Methy Propan-2-ol
-NH,- SH, -0H r -C= CH- CH,Mgl CI
(CH ) C-OH +Cr (2CH, from - NH,)
17.(b) 23. (b)
18. (b) 24. (b) The commercial alcohol is made unfit for drinking by
mixing in it some copper sulphate (to give it colour)
-ONa and pyridine (a foul smelling liquid). It is known as
19. (2) denaturation of alcohol.
+CO,
Oxidation
Sodium 25. (b) CH,CH,CH,CH,OH ’ CH;CH,.CH,CHO
Phenoxide

OH OH OCH,
OH
H,SOA

COONa
26. (a) CH, Sc-CH, CHOH ,
H,SO4 H,c-c-cH,
COOH
Salicylic acid CH, CH,
27. (c) Electron withdrawing group stabilises the benzene ring
JCH, CO), 0 due to delocalisation of charge.
-CH, and-CH,OH are electron donating group and
hence decrease the stability of benzenering-0CH,
is weaker electron withdrawing group than -COCH,.
co--u. Hence-COCH, group more stabilize the phenoxide
ion at p-position.
COOH
+CH,COOH 28. (d) This method is suitable for the preparation ofa wide
variety of unsymmetrical ethers. The nucleophilic
Aspirin substitution of halides with alkoxide leads to desired
(Acetyl Salicylate) product.
29. (c) Due to presence of methyl alcohol in liquor.
20. (b) CHçBr +C,H0Na ’CzHs-0-C,Hs
-NaBr
Sod. ethoxide diethyl ether 30. () CH-CH, -CH-CH-CH,-CH, HIO4,
21. (b)
CH, HNO, COOH
22. (c) 2CH, -CH, -CHO
CH,(Oxidation) COOH
0-Xvlene

Phenol
Phenolpthalein
H5SO4
(Y

Phthalic anhydride, X

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