Professional Documents
Culture Documents
Alcohols, Phenols
and Ethers and Ethers
Question 1.
303
Intext
IntextQuestions
Questions
Classify the following as primary, secondary and tertiary
alcohols.
CH 3
(i) CH 3 C CH 2 OH
CH 3
(ii) H 2 C == CH CH 2 OH
OH
CHCH3
(iii) CH 3 CH 2 CH 2 OH
(iv)
CH3
CHCOH
CH
CH2CHCH3
(v)
(vi)
OH
CH3
Solution.
(i)
(iii)
(v)
(vi)
Question 2.
Primary alcohol
Primary alcohol
Secondary alcohol
Tertiary alcohol
allyl alcohol
C
Secondary (2 )
allyl alcohol
Solution.
(vi)
CHCOH
CH3
CH2 ==CH C OH
Tertiary (3 )
allyl alcohol
304
(i) CH 3 CH 2 CH CH CH CH 3
CH 2 Cl
CH 3
CH 2 OH
(ii) H 3 C CH CH 2 CH CH CH 3
CH 3
OH
OH
(iii)
Br
(iv) H 2 C==CH CH CH 2 CH 2 CH 3
OH
(v) CH 3 C==C CH 2 OH
CH 3 Br
Prefix according to the C-chain; for alcohol add suffix ol; for double
bond ene; tell the position of substituents, double bond and functional
group (s).Then, given the name in the following manner.
Name of substituent with position (in alphabetical order) + parent
C-chain name + primary suffix (antiene etc.) + secondary suffix with
position (for main functional group).
Solution.
1
CH2OH
5
4
3
2
(i) CH3 CH2 CH CH CH CH3
CH3
CH2Cl
3-chloromethyl-2-isopropyl
pentan - 1-ol
1
CH2OH
2
5
4
3
6
(ii) CH3 CH CH2 CH CH CH3
OH
CH3
2,5 dimethylhexan-1,3-di-ol
Chemistry-XII
305
OH
1
2
(iii)
Br
3-bromocyclohexanol
1
OH
Hex-1-en-3-ol
4
(v)
Question 4.
CH 3
(ii)
HO
H
2
HCHO + RMgX
+ RCH2OH + Mg(OH) X. Form here, it is clear that
Solution. (i)
Dry ether
Methanal
Isopropyl
magnesium
bromide
[(CH3)2 CH CH2OMgBr]
Addition compound
Mg(Br)OH H2O/H +
(CH3)2CH CH2OH
Isobutyl alcohol
or
Chemistry-XII
2-methylpropan-1-ol
306
MgBr
Dry ether
(ii) HCHO +
CH2OMgBr
Intermediate
product
Methanal Cyclohexyl
magnesium
bromide
H2O/H
CH2OH
Mg(OH)Br
Cyclohexyl
methanol
2
(i) CH 3 CH==CH 2
O
CH2COCH3
NaBH4
(ii)
NaBH
4
(iii) CH 3 CH 2 CH CHO
CH 3
Solution.
H O /H
2
(i) CH3 CH == CH2
CH3 CH CH3
Markownikoff's
Propene
rule
OH
Propan-2-ol
2
1
(ii)
O
methyl-2-oxocyclohexyl
ethanoate
Chemistry-XII
OH
CH2COCH3
NaBH4
Reduction
CH2COCH3
O
Methyl (2-hydroxycyclohexyl)
ethanoate
307
NaBH
4
(iii) CH3 CH2 CH CHO
Reduction
CH3
2-methylbutanal
CH3
2-methylbutan-1-ol
HCl ZnCl
2
(a) CH3 CH2 CH2 CH2 OH
Butan-1-ol(1)
HBr CH CH CH CH Br + H O
3
2
2
2
2
Heat
1-bromobutane
SOCl 2
Lucas reagent
OH
2- methylbutan-2-ol (3)
CH3
Cl
2-chloro-2-methylbutane
Chemistry-XII
308
CH3
CH3
HBr
(b) CH3 C CH2 CH3
CH3 C CH2 CH3
eat
H
Br
OH
2- methylbutan-2-ol
2-bromo-2-methylbutane
+ H2O
CH3
CH3
2
2
4
4
1
3
1
3
SOCl 2
(c) CH3 C CH2 CH3
CH3 C CH2 CH3
Heat
OH
Cl
2-chloro-2-methylbutane
+ SO2 + HCl
Note *Butan-1-ol, being primary alcohol requires heating with Lucas
reagent. 2-methyl butan-2-ol being tertiary alcohol reacts without heating.
*Lucas test is used to distinguish between primary, secondary and tertiary
alcohols.
Question 7.
CH3
Solution. (i)
OH
H (Heat)
H2O
1-methyl
cyclohexanol
CH2
CH3
+
1-methyl
cyclohexene
(Major)
1-methylene
cyclohexane
(Minor)
H + , heat
H 2O
But- 2-ene
(Major)
Chemistry-XII
is
309
H+
H2O
H ion
shift
CH3 CH CH CH3
H
2 carbocation
(More stable)
H+
CH3 CH
CH CH3
But-2-ene
Question 8. Ortho and para nitrophenols are more acidic than phenol.
Draw the resonance structures of the corresponding phenoxide ions.
Acidic strength depends on the relative stabilities of corresponding
phenoxide ions based on resonance.
Chemistry-XII
310
O
O
N
O
N
N
O
O
O
Due to R effect of NO2 group, o- and p-nitrophenoxide ions
are more stable than phenoxide ion. Consequently, both o- and
p-nitrophenols are more acidic than phenol.
O
Chemistry-XII
Alcohols,PhenolsandEthers
311
Question 9.
Solution. (i)
CHCl2
Phenol
O Na
O Na
OH
CHO
NaOH
Intermediate
OH
CHO
Salicylaldehyde
OH
ONa
(i) CO2
NaOH
(ii)
OH
(ii) H
Sodium
phenoxide
the
2-ethoxy-3-methylpentane
pentan-2-ol.
COOH
2-hydroxybenzoic
acid
(Salicylic acid)
CH3 OH
3-methylpentan-2-ol
CH3 ONa
Sodium-(3-methyl)-pentoxide
Chemistry-XII
312
C 2H5Br
+ H2O
Bromoethane
CH3 ONa
CH3 CH2 CH CH CH3
CH3 OC 2H5
2-ethoxy-3-methylpentane
+ CH3Br
(ii)
+ CH3ONa
NO2
NO2
This reaction involves preparation of ether by Williamson synthesis. It
takes place by SN2 attack of an alkoxide ion on primary alkyl halide.
Solution.
ONa
(ii)
OCH3
+ CH3Br
+ NaBr
NO2
NO2
1-methoxy-4-nitrobenzene
(ii)
+ HBr
OC2H5
(iii)
Conc. H2SO4
Conc. HNO3
HI
(iv) (CH 3 ) 3 C OC2H 5
Chemistry-XII
Alcohols,PhenolsandEthers
Alcohols,PhenolsandEthers
313
313
primary halide is
primary halide is
place at o- and
place at o- and
OC2H5
OC2H5
+ HBr
+ HBr
(ii)
(ii)
Ethoxy benzene
Ethoxy benzene
OH
OH
+ C2H5Br
+ C2H5Br
Phenol
Phenol
OC2H5
OC2H5 Conc. H2SO4
2 OC2H5
2 OC2H5
1
1
Conc. H2SO4
Conc. HNO3
Conc. HNO3
(iii)
(iii)
Ethoxy benzene
Ethoxy benzene
NO2
NO2
2-ethoxy2-ethoxynitrobenzene
nitrobenzene
+
+
O2N
O2N
1
1
4 OC2H5
4 OC2H5
3
3
2
2
4.-ethoxy4.-ethoxynitrobenzene
nitrobenzene
HI
t butyl iodide
Ethanol
Exercises
Exercises
Exercises
CH
(i) CH 3 CH CH C
(i) CH 3 CH CH C CH 33
CH
CH
3
3 OH
CH 3 OH CH 3
(ii) H 3 C CH CH 2 CH CH CH 2 CH 3
(ii) H 3 C CH
CH 2 CH
CH
CH 2 CH 3
OH
OH
CH
OH
OH C22H 55
Chemistry-XII
314
(iii) CH 3 CH CH CH 3
OH OH
(iv) HO CH 2 CH CH 2 OH
OH
CH3
CH3
OH
(v)
(vi)
OH
CH3
CH3
OH
(vii)
(viii)
OH
CH3
CH3
(ix) CH 3 O CH 2 CH CH 3
CH 3
(x) C6H 5 O C2H 5
(xi) C6H 5 O C7 H15 ( n)
(xii) CH 3 CH 2 O CH CH 2 CH 3
CH 3
Prefix according to the carbon chain; for alcohol (OH) use suffix -ol; tell
the position of substitutents and functional group. For ether ( O ),
prefix alkoxy is used. For OH group attached directly to benzene ring,
suffix phenol is used.
So, give the name of alcohol as substituent with position (in alphabetical
order) + prefix of carbon chain + primary suffix (ane, ene, yne) + ol with
position and give the name of ether as alkoxy alkane (where alkoxy
smaller R group and alkane is main chain)
CH3
1
2
Solution. (i) CH3 CH CH C CH3
CH3 OH CH3
5
2, 2, 4-trimethyl pentan-3-ol
Chemistry-XII
Alcohols,PhenolsandEthers
1
315
6
OH
OH C 2H5
5-ethyl heptane-2, 4-diol
1
OH OH
Butane-2, 3-diol
1
(iv) HO CH2 CH C H2 OH
OH
Propane-1, 2, 3-triol
CH3
CH3
OH
(v)
(vi)
2
1
OH
2-methylphenol
4-methyl phenol
CH3
CH3
(vii)
(viii)
3
2
OH
1
2 CH
3
3
2,6-dimethyl phenol
OH
CH3
2,5-dimethyl phenol
1
CH3
(x)
C 6H5 O C 2H5
Ethoxybenzene
1- methoxy-2-methyl propane
1
CH3
2-ethoxybutane
Chemistry-XII
316
(vii) Cyclohexylmethanol
(ix) Cyclopent-3-en-1-ol
(viii) 3-cyclohexylpentan-3-ol
(x) 3-chloromethylpentan-1-ol
(i) Draw the main carbon chain according to the root word of carbon
chain and then attach the other groups according to the positions
mentioned.
(ii) Suffix al represents OH group and prefix alkoxy repersents RO
group.
CH3
OH
2-methylbutan-2-ol
1
OH
1-phenylpropan-2-ol
CH3
OH
1
2
4
6
3
5
(iii) CH2 CH2 C CH2 C CH3
OH
OH
CH3
3, 5-dimethylhexane-1, 3-5-triol
OH
1
2 C2H5
1
(iv)
C2H5
1-ethoxypropane
2,3-diethyl phenol
1
OC 2H5 CH3
2-ethoxy-3-methyl pentane
OH
1
CH2OH
(vii)
(viii) CH3CH2CCH2CH3
Cyclohexyl methanol
3-cyclohexylpentan-3-ol
Chemistry-XII
Alcohols,PhenolsandEthers
317
OH
(ix)
1
2
3
Cyclopent-3-en-1-ol
1
CH2Cl
3-chloromethylpentan-1-ol
Solution.
CH3
3-methyl butan-1-ol
4
CH3
2-methyl butan-1-ol
CH3
CH3
2, 2-dimethyl propan-1-ol
5
OH
Pentan-2-ol
Chemistry-XII
318
OH
CH3 OH
2-methyl butan-2-ol
3-methyl butan-2-ol
5
OH
Pentan-3-ol
(ii) Primary : (a), (b), (c) and (d); Secondary (e), (f), (h) Tertiary : (g).
Question 4. Explain why propanol has higher boiling point than that of
the hydrocarbon, butane?
Boiling point is directly proportional to the intermolecular forces existing
in a compound.
H O H O H O
C 3H7
C 3H7
C 3H7
Solution. Water and alcohols both are polar in nature. When an alcohol
is dissolved in water, it forms hydrogen bonds with water by breaking
the H-bonding already existing between the water molecules.
Hydrocarbons are non-polar in nature and do not form H-bonds with
water molecules. Therefore, alcohols are readily soluble in water
whereas hydrocarbons are not.
R O H O H O
+
H
R
H
Hydrogen bonding among alcohol and water
Chemistry-XII
Alcohols,PhenolsandEthers
319
H
BH2
CH3 CH== CH2
3H 2O 2 , OH
CH CH ==CH
3
2
(CH3 CH2 CH2)3 B
H 2O
(CH3 CH2 CH2)2 BH
Boric acid
OH
OH
2 CH3
CH3
2-methyl phenol
or
o- cresol (I)
3-methyl phenol
or
m cresol (II)
CH3
4-methyl phenol
or
p-cresol (III)
Question 8.
Chemistry-XII
320
N+
O
H
O
o-nitrophenol
+
HO
NO
HO
NO
O Intermolecular
H-bonding
p-nitrophenol
CH3
Solution.
CH3
H3CCH
H3CCOOH
+
O2
Cumene
or
(Isopropyl benzene)
H
H2O
Cumene
hydroperoxide
OH
O
+
CH3CCH3
Phenol
Propanone
(Acetone)
Question 10. Write chemical reaction for the preparation of phenol from
chlorobenzene.
Reaction of chlorobenzene with
acidification of the product formed.
Chemistry-XII
sodium
hydroxide
followed
by
Alcohols,PhenolsandEthers
Solution.
321
Cl
O Na
+ NaOH
OH
623 K
HCl
300 atm
Chlorobenzene
Sodium
phenoxide
Phenol
+H
+ H2O
H
C
H
+
+ H2O
H
C
H
C
H + H2O
OH
+ H3O
Question 12. You are given benzene, conc. H 2SO 4 and NaOH. Write the
equations for the preparation of phenol using these reagents.
(i) Sulphonation of benzene.
(ii) Reaction with NaOH and water.
Chemistry-XII
322
SO3H
Solution.
H2SO4 (Conc.)
NaOH
Heat
H2O
Benzene
SO3 Na
Benzene
sulphonic
acid
Sodium benzene
sulphonate
OH
ONa
+
Phenol
Sodium phenoxide
2
4
Solution. (i) C 6H5 HC == CH2 + H2O
Markownikoff's
rule
Ethenylbenzene
(Styrene)
C 6H5 CH CH3
OH
1-phenyl ethanol
CH2Br
(ii)
CH2OH
+ NaOH(aq)
+ NaBr
Cyclohexyl
methyl bromide
5
Cyclohexyl
methanol
1
(iii) CH3 CH2 CH2 CH2 CH2 Br + KOH CH3 CH2 CH2 CH2 CH2 OH
1-bromopentane
(aq )
Pentan-1-ol
+ KBr
Chemistry-XII
Alcohols,PhenolsandEthers
323
Question 14. Give two reactions that show the acidic nature of phenol.
Compare acidity of phenol with that of ethanol.
Reaction of phenol with Na and NaOH; comparing of acidity of phenol
and ethanol.
+ 2Na
Phenol
+ H2
Sodium phenoxide
(ii) Reaction with sodium hydroxide Forms sodium salt and water.
OH
ONa
+ NaOH
Phenol
+ H2O
Sodium phenoxide
II
III
IV
Question 15. Explain why is ortho nitrophenol more acidic than ortho
methoxyphenol?
(i) NO 2- electron withdrawing group. OCH3-electron releasing group.
(ii) Presence of electron withdrawing group increases the stability of
phenoxide ion while presence of electron releasing group decreases
its stability.
(iii) Higher is the stability of phenoxide ion formed, more is the acidic
character.
Chemistry-XII
324
O
NO2
NO2
+ H
o-nitrophenol
OH
O
OCH3
OCH3
+H
O
O
CH3
O
O
CH3
OH
OH
OH
Chemistry-XII
OH
Alcohols,PhenolsandEthers
325
(i)
(ii)
(iii)
(v)
4
Solution. (i) CH3CH2CH2OH
CH3 CH2 CHO
(Oxidation)
Propan-1-ol
Propanal
KMnO 4 /OH
CH3CH2COOH
(Oxidation)
OH
OH
Br
Br2/CS2
(ii)
Propanoic acid
OH
+
HBr
Br
Phenol
o-bromophenol
OH
OH
OH
NO2
+
HNO3(dil.)
(iii)
p-bromophenol
H2O
NO2
Phenol
o-nitrophenol
OH
ONa
CHCl3/NaOH (aq)
(iv)
p-nitrophenol
OH
CHO
H2O/H
CHO
343 K
Phenol
Salicylaldehyde
Kolbe's reaction.
Reimer-Tiemann reaction.
Williamsonethersynthesis.
Unsymmetricalether.
Chemistry-XII
326
NaOH
(ii) H
Phenol
2-hydroxybenzoic
acid
(Salicylic acid)
Sodium
phenoxide
O Na
OH
CHCl2
Phenol
Intermediate
OH
O Na
CHO
CHO
NaOH
Salicylaldehyde
(iii) Williamson
ether
synthesis Ethers
(symmertical
and
unsymmertrical) are prepared by this method. It involves the
reaction of an alkyl halide with sodium alkoxide.
R X + RONa R O R + NaX
e.g., 1. (CH3)3 C ONa + CH3Br CH3OC (CH3)3 + NaBr
RX
Chemistry-XII
Alcohols,PhenolsandEthers
327
Ethanol
Protonated ethanol
(Ethyl oxonium ion)
Propene propan-2-ol.
Benzylchloride Benzylalcohol.
Ethylmagnesiumchloride Propan-1-ol.
Methylmagnesiumbromide 2-methylpropan-2-ol.
(i)
(ii)
(iii)
(iv)
CH CH CH
3
3
OSO3H
Chemistry-XII
H O
OH
Propan-2-ol
328
CH2OH
+ NaOH (aq)
Hydrolysis
(ii)
+ NaCl
Benzyl
chloride
Benzyl
alcohol
OMgCl
O
Dry
(iii) CH3CH2MgCl + H C H C H
ether
Ethyl magnesium
H2CCH3
chloride
H
Methanal
Adduct
OH
H 1C H
2
CH23 CH3
H 2O / H +
Propan-1-ol
(iv)
CH3MgBr
Methyl magnesium
bromide
H3C C
CH3
Propanone (Acetone)
OMgBr
H3C C CH3
CH
3
H 2O / H +
Aduct
OH
3
H3C1 2C CH3
CH3
2 - methyl propan - 2 - ol
Oxidationofaprimaryalcoholtocarboxylicacid.
Oxidationofaprimaryalcoholtoaldehyde.
Bromination ofphenolto2,4,6-tribromophenol.
Benzylalcoholtobenzoicacid.
Dehydrationof propan -2-ol topropene.
Butan-2-one to butan-2-ol.
(i)
(ii)
(iii)
(iv)
(v)
(vi)
Chemistry-XII
Alcohols,PhenolsandEthers
Solution.
(i)
329
Question 22. Give reason for the higher point of ethanol in comparison
to methoxymethane.
Presence of intermolecular H-bonding in ethanol, but not in ether.
H O H O H O
C 2H5
C 2H5
C 2H5
CH3
(iii) O2N C6H 4 OCH 3 ( p)
H3C CH3
(ii) CH 3 OCH 2 CH 2 Cl
(iv) CH 3 CH 2 CH 2 OCH 3
(v)
(vi)
OC2H5
OC2H5
Solution.
CH3
1-ethoxy-2-methylpropane
1
OCH3
2-chloro-1-methoxyethane
or
3
4
NO2
4-nitroanisole
Chemistry-XII
330
H3C
CH3
(v)
(vi)
2
1
OC2H5
OC2H5
1-ethoxy-4,4-dimethyl
cyclohexane
Ethoxy
benzene
Question 24. Write the names of reagents and equations for the
preparation of the following ethers by Williamsons synthesis.
(i) 1-propoxypropane
(ii) Ethoxybenzene
(iii) 2-methoxy-2-methylpropane
(iv) 1-methoxyethane
Williamson's
synthesis
(i) R X + RO Na
R O R + Na X
(ii) Alkyl halide should be primary.
Solution.
Heat
Sodium propoxide
1-bromopropane
O Na
(ii)
+ CH3CH2Br
Sodium
phenoxide
Heat
Bromoethane
OCH2CH3
+
NaBr
Ethoxybenzene
Chemistry-XII
Alcohols,PhenolsandEthers
(iii)
CH3
CH3 C O Na+
CH3
331
C H3 Br
Heat
Bromomethane
Sod. tert-butyl-alkoxide
CH3
CH3
2-methoxy-2-methylpropane
CH3 Br
Heat
CH3CH2 O CH3
Bromomethane
Sodium ethoxide
1-methoxyethane
+ NaBr
C 2H5Br
+ Na+O C CH3 C 2H5 O C CH3
Ethyl bromide
CH3
CH3
tertiary butyl ethyl ether
+ NaBr
CH3
H3C C Br
CH3
Tert. butyl bromide
CH3
2-methyl propene
(Ether is not formed)
+ NaBr + C 2H5OH
(ii) Aryl halides and vinyl halides cannot be used as substrates
because they are less reactive in nucleophilic substitution.
Chemistry-XII
332
Propan-1-ol
Sodium propoxide
Reaction mechanism
Dry ether
Heat
1-bromopropane
or
(ii) By dehydration of 1-propanol with conc. H 2SO4 at 413 K.
H SO
2
4
CH3CH2CH2 O+
CH3CH2CH2OH + H+
Propan-1-ol
H
H
Protonated 1-propanol
CH3CH2CH2 O H + CH3CH2CH2 O+
H
H
Propan-1-ol
413 K
H 2O,
+
H
CH3CH2CH2 O CH2CH2CH3
H+ ,
1-propoxypropane
Chemistry-XII
Alcohols,PhenolsandEthers
333
Conc. H SO
2
4 CH CH==CH
CH3 CH OH
3
2
413 K
Propene
(major)
CH3
Propan-2-ol
(2 alcohol)
CH3
CH3
+ CH3 CH O CH CH3
Di-isopropyl ether
(minor)
CH3
CH3
Conc. H 2SO 4
CH3 C OH
CH3 C== CH2 + H2O
413 K
CH3
Solution.
HI
(i) CH3CH2CH2 O CH2CH2CH3
1-propoxypropane
373 K
CH3CH2CH2 OH + CH3CH2CH2 I
Propan-1-ol
OCH3
HI, 373 K
(ii)
Iodopropane
OH
Methoxybenzene
+ CH3I
Phenol
CH2OC2H5
Iodomethane
CH2I
HI, 373 K
(iii)
Benzyl ethyl ether
+ C2H5OH
Benzyl iodide
Ethanol
Chemistry-XII
334
OR
OR
OR
OR
IV
III
II
Br
Br2
CH3COOH
Br
Anisole
o-bromo-anisole
(minor)
p-bromo-anisole
(major)
H
+
Protonation
CH3 O CH3 + I
fast
H
+
SN 2
StepII I + CH3 O CH3
Slow
CH3 I
Iodomethane
+ CH3OH
Methanol
Chemistry-XII
Alcohols,PhenolsandEthers
335
H
+
Protonation
StepIII CH3 O H + H I CH3 O H + I
fast
Protonated methanol
H
+
SN 2
StepIV I + CH3 O H
CH3 I
Slow Iodomethane
+ H2O
OCH3
+ CH3Cl
Anisole
Anhyd. AlCl3
Chloromethane
OCH3
CH3
+
CS2
2-methoxy toluene
(Minor)
CH3
4-methoxy toluene
(Major)
OCH3
H2SO4
OCH3
NO2
+
HNO3
Anisole
2-nitroanisole
(Minor)
NO2
4-nitroanisole
(Major)
Chemistry-XII
336
OCH3
OCH3
Br
Br2 in
Ethanoic acid
Anisole
o-bromo
anisole (Minor)
Br
p-bromoanisole (Major)
Anhyd. AlCl3
Ethanoyl
chloride
OCH3
OCH3
COCH3
+
2-methoxy
acetophenone
(Monor)
COCH3
4-methoxy acetophenone
(Major)
Question 32. Show how would you synthesise the following alcohols
from appropriate alkenes?
CH3
(i)
OH
OH
(ii)
OH
(iii)
(iv)
OH
Chemistry-XII
Alcohols,PhenolsandEthers
337
Solution.
CH3
(i)
CH3
CH3
H2O
OH
H
1-methyl
cyclohexene
Tert. carbocation
CH3
H+
OH
1-methylcyclo-hexan-1-ol
OH
(ii)
+ HOH
4-methyl hept-3-ene
H
Markownikoff's
rule
4-methyl heptan-4-ol
OH
+
(iii)
+ HOH
Pent-1-ene
Penan-2-ol
(iv)
4
H2O
H
2-cyclohexylbut
-2-ene
OH
2-cyclohexyl
butan-2-ol
HBr
CH 3 CH CH CH 3 CH 3 C CH 2 CH 3
Br
CH 3
CH 3 OH
Give a mechanism for this reaction.
The secondary carbocation formed in the process rearranges to a more
stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.
Chemistry-XII
338
Solution. Mechanism
H2O
HBr
CH3 CH CH CH3
CH3 CH CH CH3
Br
CH3 O H
CH3 OH
3-methylbutan-2-ol
H
H
H ion shift
CH3 C CH CH3
CH3
2 carbocation
(Less stable)
Br
CH3
CH3
Br
3 carbocation
(More stable)
2-bromo-2-methyl
butane
OH
OH
OH
Propane-1,2,3-triol
(i) CH 3 CH CH CH CH CH 3
CH 3 OH C2H 5 OH
Solution.
(ii)
2
1
OCH3
CH 3 CH 2 C ==C OH
1
CH 3 CH 2 OH
Solution.
Chemistry-XII
3-methylpent-2-ene-1, 2-diol.