Chapter 16 OH LaNun
Chapter 16 OH LaNun
Chapter 16 OH LaNun
Phenol dissolve in aqueous NaOH because it is a weak acid. It react with strong
base NaOH to form soluble salt.
OH ONa
NaOH
+ H2O
soluble salt
ii) Ethanol reacts with iodine in aqueous solution of sodium hydroxide forming
yellow precipitate but 1-propanol does not
• Ethanol gives +ve test with Iodoform reagent, because it has methyl alcohol
structure, when it oxidised with Iodoform reagent a methyl carbonyl structure
compound is formed.
• 1-propanol gives –ve test with Iodoform reagent, no methyl alcohol structure.
iii) Write a chemical equation for the reaction between ethanol and iodine in aqueous
solution of sodium hydroxide.
O
I2, NaOH
CH3CH2OH CH3CH
I2, NaOH
O
CHI3 + HCO
yellow ppt
June 99 a) Give suitable chemical tests to distinguish the following pairs of compounds by
2. specifying the necessary reagents, appropriate observations and chemical
equations involved.
i. C6H5CH2OH and C6H5OH
ii. CH3CH(OH)CH2CH2CH3 and (CH3)2C(OH)CH2CH2CH3
1
Scheme past year semester 2- 1 Edition
i) Benzyl alcohol react with Lucas’s reagent, solution turns cloudy immediately,
phenol does not react with Lucas’s reagent.
Lucas reagent
ZnCl2, HCl
CH2OH CH2Cl
ii) 2-pentanol reacts with acidified KMnO4, purple colour disappear, brown
precipitate is formed. 2-methyl-2-pentanol does not react, purple colour
remain.
KMnO4,/H+
O
CH3CH(OH)CH2CH2CH3 CH3CCH2CH2CH3 + MnO2
brown precipitate
i)
H2SO4(con)
HOCH2CH2CH3 H2C CHCH3
heat
KMnO4,/OH-
cold
H2C CHCH3
OH OH
ii)
Cl MgCl
Mg/ether
i. HCHO
ii. H3O+
CH2OH
iii)
O CH3
i. CH3MgBr OH
ii. H3O+
2
Scheme past year semester 2- 1 Edition
June 00 Based on the molecular formula of C6H14O, draw the structural formulae for two
3. tertiary alcohols. Then draw and label the structural formula of an alcohol which
contains primary and secondary carbons atoms. State whether this alcohol is
optically active
CH3 CH3
CH3CCH2CH2CH3 CH3CH2CCH2CH3
OH OH
(I) (II)
C6H14O
CH3
CH3CHCH2CHCH2OH
OH
20 10
CH2OH CH2OH
C C
H H
CH2CH3 H3CH2C
OH OH
Show the mechanism for the formation of the major product. Draw the structure of
another possible product and state the rule applied in determining the major
product.
CH3 CH3
H2SO4(con)
CH3
heat
OH CH3
major product
3
Scheme past year semester 2- 1 Edition
Mechanism:
CH3 CH3
CH3 + H+ CH3
OH OH2
CH3 CH3
CH3 CH3
OH2
CH3 CH3
H+
CH3 CH3
Other product:
CH3 CH3
or
CH3
CH3
2001/02 A compound AA, C3H8O reacts with phosporus pentachloride, PCl5 to form
Session compound BB. Compound AA forms a cloudy solution in 5 minutes after the
5. addition of Lucas reagent. Compound BB reacts with magnesium in ether solvent
to produce CC. The reaction between CC and carbon dioxide, followed by
hydrolysis yields DD. By giving appropriate reasons, draw the structural formulae
of AA to DD and the structural formula for an isomer of AA.
PCl5
C3H8O BB
AA
Lucas's reagent
AA HCl, ZnCl2
cloudy after 5 mins.
BB Mg/ether
CC
i.CO2
ii. H3O+
CC DD
4
Scheme past year semester 2- 1 Edition
MgCl
OH
AA: CC: CH3CHCH3
CH3CHCH3
Cl COOH
BB: CH3CHCH3 DD:
CH3CHCH3
Reasons:
* AA is a secondary alcohol as it react with Lucas’s reagent
moderately (cloudy after 5 mins).
Isomer AA is CH3CH2CH2OH
COOH COOCH2CH3
CH3CH2OH/H+
CH3CHCH3 CH3CHCH3 + H2O
heat
ester
DD
H CH3 H
5
Scheme past year semester 2- 1 Edition
i) 4,6-dimethyl-2-octanol
ii) Yes, A is optically active because at least there are 3 chiral carbon, at carbon
number 3, 4 and 6.
iii) A is secondary alcohol.
iv) Product of the dehydration of A:
Major product:
7. Given below are the observations from experiments carried out on an alcohol,
C4H10O which has several isomers.
(i) Isomer L does not show any changes upon mixing with Lucas reagent but it
forms butanoic acid upon oxidation with acidified potassium dichromate (IV).
(ii) Isomer M is optically active and gives positive test with I2/NaOH.
(iii)Isomer N reacts instantly with Lucas reagent but it does not change the purple
solution of acidified potassium manganate (VII).
6
Scheme past year semester 2- 1 Edition
HCl, ZnCl2
(i) L no reaction
KMnO4/H+
L CH3CH2CH2COOH
(ii) M
I2, NaOH
CHI3
yellow precipitate OH
M is CH3CH2 C CH3
H
2-butanol
KMnO4/H+ no reaction
N
* N is tertiary alcohol, fast reaction with Lucas test & does not oxidised by KM
OH
N is H3C C CH3
CH3
2-methyl-2-propanol
Suggest how the above compound can be synthesized using benzene and phenol
con.H2SO4
NH2 N2Cl
NaNO2, HCl
<5oC
N2Cl + OH N N OH