DUld

[CBSE Delhi 20130CI

Q.7. How is toluene obtained from phenol?
OH CH3
+CH CVAnhyd. AICl
Ans. Zn(dust)
A
Toluene
Phenol
a aala and ar 393
0.2. How will you convert:
() Propene to Propan-1-o1? [CBSE Delhi 2013]1
(i) Ethanal to Propan-2-01?
CHCHCH,Br KOHA(a4)
Peroxide
Ans. () CHCH=CH2 +HBr - CH,CH,CH,OHH
Propene Propan- 1-ol

(i)
CH3 CHMgl CH
CHN OMgl H, HO CHs OH

H H H CH3
Ethanal Propan-2-ol
ICRSE (AN 20081
 Benzylalcohol
0.4. How would you obtain
() picric acid (2, 4, 6-trinitrophenol) from phenol?
()2-Methylpropene from 2-Methylpropanol? [CBSE Delhi 2011]

QH QH QH

Ans. () HSO4 (conc.) SO,H HNO (conc.)

O;N ONO2
Phenol
SOH NO
Picric acid
Phenol-2,4
disulphonic acid
CHa CH3
CH3
(ii) CH3-CH-CH,OH +SOCl2 CH-CH-CH2-Cl +KOH (alc.) CH-C= CH2
2-methyl propene
2-Methyl propanol
 4-Methoxy acetophenone
write
Q.3. W the main
product(s) in each of the (Major)
CH3 following reactions: ICBSE Delhi 2016]

CH-CH-0-CH3 +HI (i) CH-CH=CH BH

() 3H0,/OH
CH3
( ) CHs-OH9ag. NaOH
(i) CO2, H*
CH3 CH3
Ans. () CH3-CH-0-CH3 + H- - CH-C-I + CH-OH
Methy!
CH3 CH3 alcohol
Methyl Tert. butyl iodide
tert. butyl ether

) B2H6
(i1) CH3-CH-CH3 CH-CH-CH-OH
(it) 3H2O2/OH n-propyl alcohol

OH OH
COOH
() aq NaOH
(iii) (ii) CO/H
Salicylic acid
Phenol
 PropallFa

Q.6. How do you convert the following:

) Phenol to anisole i) Propan-2-ol to 2-methylpropan-2-o1
() Aniline to phenol BSE Delhi2
+
OH ONa OCH3
Ans. () +CHBr
+NaOH
Phenol Anisole

OH O OH

(i) CH-CH-CH3-PCC CH3-C-CH 0 CH3MgBr CH-C-CH3

i) H2O
Propan-2-ol
CH3
2- methyl propan-2-ol

NH2 NCI OH

(ii) NaNO,/HCI HO
273-278 KK Warm
Aniline
Phenol
Q.7. Explain the mechanism of the following reactions:
()Addition of Grignard's reagent to the carbonyl of
followed by hydrolysis. group compound forming an adud
a

(ii) Acid catalysed dehydration of an alcohol

forming an alkene.
(ii) Acid catalysed hydration of an alkene
forming an alcohol. [CBSE Delhi 2009; (AI) 2012] [HOID)
Ans. (i) Step Nucleophilic addition of Grignard
I:
reagent to carbonyl group.

+R-Mg-X C-OMg-X
R
Adduct
 Step l1: Hydnolysis

-OMg-x 11,0
R
2S=OH+ Mg(O1)X
R
CHCH;-OH
Mechanis:
CH CH +H,0
Step I: Formation of protonated alcohol

H- + H Fast
H-C-¢-O-H
H
H H
Ethyl alcohol
Ethyl oxonium ion

Step 11: ormation of carbocation: It is the slowest step and hence, the rate determining step.

H H
Slow +
H-¢ H-C-C +HoO
H H H H
Ethyl oxonium ion Ethyl carbocation

Step IlI: Formation of ethylene by elimination of a proton

H H
H- +H
H H
Ethyl carbocation Ethylene
To drive the equilibrium to the right, ethylene is removed as it is formed.

H
Cin =cK + H20
Alkene

Mechanism:
attack of H,O".
Step I: Protonation of alkene to form carbocation by electrophilic
H+H H,O

carbocation.
Step II: Nucleophilic attack of water
on

. HO
alcohol
form
Step Ill: Deprotonation to
an

A :OH

+ HO +HO
 tert-butyl chloride
Q.3. Write the formula of (Turbidity appears immediately)
(a) Bromination of reagents used in the following reactions:
phenol to 2, 4,
b) Hydroboration of propene and6-tribromophenol
then oxidation to
() Arrange the propanol.
following compound groups in the
(a) p-nitrophenol, increasing order of their property
ethanol, phenol (acidic character) inaicateu
(b) Propanol, propane, propanal (boiling
(ii) Write the mechanism (using point)
curved arrow notation) of the
+ following reaction:
CH-CH-ÖH,CH,CH,oH CH3-CH2-0-CH-CH, + H,0 [CBSE Delhi 2017]
Ans. a)Br,(aq) H
(b) B.H, HO, H,O2 and OH
(ii) (a) Ethanol< Phenol <p-nitrophenol
(b) Propane < Propanal < Propanol
H H H
(in) CHy-CH2-0: + CH-CHo-H CH-CH-0-CH-CH + H,O
****