SRM

Nandhivaram
PUBLIC
Guduvanchery
SCHOOL
Chennai 603202 Worksheet
s. Reste
Name Grade XIlB
Subject CHEMISTRY Issued Date Submission Date>

Chapter / Topic Unit-7 - Alcohols,Phenol and Ethers

Aloho'sAlcohols
Level 1:
1.The Hydroboration-Oxidation process proceeds throygh:
a) Markovnikov rule b) Saytzeff rule Ant-markovnikoV rule d) Anti-Saytzeff rule
2.Upon reacting with Grignard's Reagent; formaldehyde forms:
a) Primary alcohol b) Secondary alcohol c) Tertiary alcohol d) Quarternary alcohol
3. The reaction of Lucas reagent is fastest with
a) (CH3)sCOH b) (CHs)2CHOH c) CH3(CH2)20H d) CH3CH20H
4. What is the IUPAC name of CH,(OH)- CH,(0H) and CH, = CH- CH20H?
5. Write the IUPAC name of the following:
CH, frg-en- tol
OH
2,5-donatiy! heal
CH,

6. Write the IUPAC name of the following compound:

Hee--en-3
CH,
H,C=CH-CHCH,--CH,CH, CH, --
CH =CH CH: - OH -CH,CH,-OH
Br -SH,oHi-bems-3mstg
3Haylo-2-en-lol 2-feny-Phan l
7. Write the structure of the molecule of a compound whose
IUPAC name is 1- phenylpropan-2-ol.
8. Draw the structure of hex--en-3-ol
9. Lower alçohols are soluble in water. Justify OH
43o10. Propanol has higher boiling point than butane. Give reason.hee to an deal
11.a) What is degatured alcohol? ’ CHhot t
b) Menion two important Coso
H- Benttr. L 5 g u s e s gt methapol.
12.Arrange the following compound groups in the
(0 p-nitrophenol, ethanol, phenol (acidic character) increasing order of their property indicated:
eonol fhene p-netefleuol
(O Propanol, Propane, Propanal (boiling point)
Level 2:
pfme faofaual > frofomal
H -Bon
1. Ethanol on heating with conc. H2SO at 443 Kgives- olllwson
sysrcttau -S N meh
a) diethylsulphate b) Ethene c) Diethyl ether d) Ethyl hydrogen sulphate
2. The correct order ot boiling points for primary (1), secondary (2') and tertiary
1>2>3 bj3 >2>1 c) 2 >1' >3 d) 2>3 >1 alcohol (3') is..
 CHy-(H-CH-CH -cHs

3.UPAC name of the compound HCCH(OH)CH2CH(CH3)CH3 ls.

a) 4-methylpentene-2- ol b)2-methylpentanol - 4
c) 4,4- dimethyl- butan-2-ol 4-methyl pentan -2-ol
9In the reaction given below, Xis: H;SO*
Neopentyl alcohol +X
a) 2-methylpent-2-ene b) 2-metthylpentane cy2-methylbut-2-ene d) neopenlane
5. On oxidation, an alcohol gave aproduct Xwhich reduced Tollens reagent. Which of the following could the alcohols
be? P) CH -CH- CH,OH Q)CH3 -CH, -CHOH - CH R) CH,- CH2 -C(CH)2 -OH
a) only P b) only P or Q c) only Qor R d) any of P, Q
or R
6. Write the mechanism of acid catalysed hydration of propene.
7.Write the equation to prove the acidic nature of alcohol and phenol.
8. How would you convert the following:
(0) Propanone to 2-methylpropan-2-ol
(1) Propene to propan-2-ol
9. How are the following conversions carried out?
() Propene to propan-2-ol () Ethyimagnesium choride to pròpan-1-ol.
10.How are the following conversions carried out?
(0) Benzyl chioride to benzyl alcohol, (i) Methyl magnesium bromide to 2-methylpropan-2-ol
11.Arrange CsHsOH, CzHsOH &Hz0 in the increasing order of acid strength.
12. Distinguish chemically primary, secondary and tertiary alcohol.
13. Give simple chemical tests to distinguish between the given pair of compounds: Propanol and 2-methypropan-2-ol
14. Convert: Ethylchloride to ethanal.
15. Identify main product of the given reaction
PCC
CH,CH =CH--CH,-OH -’?
16. Explain the mechanism of the following reaction:
H"
CH,-CH,-OH 443 K + CH,=CH, + H,0
HBr
CH,CH,0H CH,CH,Br + H,0
Level 3: cH,ecHC
1.treatment
An organic compound A' having molecular formula CaHs on treatment with áqueous H2SO gives 'B' which on
with HCIZnClz gives C. The compound Con treatment with ethanolic KOH gives back the compound 'A'.
dentity the compounds A, B, C cHe- cH Cu ct
2. Acompound 'A' (CaH1o0) is optically active. On mild oxidation, it gives acompound 'B' but on vigorous oxidation
gives another compound'C.Calong with Dis also formed from Bby reaction with iodine and alkai. Deduce the
structures of A, B, C, D.
3. Acompound 'A' having molecular formula CaHio0 is found to be soluble in concentrated sulphuric acid. It does not
react with sodium metal or potassium pemanganate. On heating with excess of HI,itgivesa single alkyl halide. Deduce
the structure of compound A and explain all the reactions.
4.Propene is subjected to two different reactions:
() reaction with water followed by acidic hydrolysis
(ü) reaction with diborane followed by oxidation with hydrogen peroxide in aqueous sodium hydroxide
State the following about the products formed in the two reactions:
(a) the molecular formulae (b) the functional group present in the molecules (c) the difference between the two
products
5. An alcohol has the fomula CsHi1OH. Draw the structural formulae of any one of its isomers
that is:
() aprimary alcoholand has a lUPACname based on propane () a secondary alcohol and has a lUPAOname
based on butane (ii) a tertiary alcohol
2
 hosse
coiugat
Phenol
Level 1:
1. The C--Obond length in phenol is less than that in methanol due to
a) partial double bond character in aromatic ring b)sp² hybridised carbon
c) sp³ hybridised carbon d) both a) and b)
is.
2. The order of acidic strength among )Phenol i) p-nitrophenol iüi) 2,4 Dinitrophenol following
b) () <(ü) <(ii) c) (i) < (ii) =(iv) d) () < (ii) < ()
a) () = (ü) =(ii)
3. Aspirin is an acetylation product of: d) m-hydroxybenzoic acid
c) o-dihydroxybenzene
a) p-dihydroxybezene b)o-hydroxybenzoic acid
4. Assertion (A): Ethanol is a weaker acid than phenol.
reaction of ethanol with aqueous NaOH.
Reason (R): Sodium ethoxide may be prepared by the
methanol. Justify.
5. The carbon oxygen bond in phenol is slightly stronger than in
6. Ortho nitrophenolhas lower boiling point than p-nitrophenol. Why ?f
7. Ortho-nitrophenol is more acidic than ortho-methoxyphenol. Why?p-nitrophenol and why?
8. Which of the following isomers is more volatile: 0-nitrophenol or
9. Arrange the following compounds in the increasing their acid
order ofphdMcfhmyd
- r k
peresol. p-nitrophenol, phenol
10. Give reason for the following:
()Dipole moment of phenol is smaller than that of methanol.
ion is treated with 'carbon dioxide.
() In Kolbe's reactions, instead of phenol, phenoxide
Level 2:
1.When Phenol is treated with CHCl3and NaOH, the product
formed is
c) Salicylic acid d) Benzoic acid
a) Benzaldehyde b) Salicylaldehyde
hydrolysis with aq. NaOH yields.
2. Monochlorination of toluene in sunlight followed by d) Benzyl alcohol
b) m-Cresol c) 2, 4-Dihydroxytoluene
a) o-Cresol
readily attacked by an electrophile?
3. Which of the following compounds will be most yPhenol d) Toluene
a) Chlorobenzene b) Benzene
6- tribromophenol on treatment with Br2
in water
4. Assertion (A): Phenol forms 2, 4,
disulphide.
Reason (R):Bromine polarises in carbon
cumene?
5. How will youobtain phenol from
benzene?
6. How will youobtain phenol from Kolbe's reaction? Soda lemulao
What is the main product formed when phenol is subjected to
7.
to benzoquinone?
8. How would you convert Phenol
from phenol?
9. How will you prepare picric acid
explain Kolbe's reaction.
10. Write the chemical reaction to
oxidized by Na2Cr207/H2SO4?
11. What happens when phenol is
heated with zinc dust?
12. What happens when phenol is distinguish between the following pairs of compounds: kMa
13. Giveaseperate chemical test to
Benzoic acid and Phenol.
(i) Ethanol and Phenol (ü)
bromine in CS;?
happens when phenol is treated with - a) bromine water b) D)
14. What
15.Convert :Phenol to 2,4,6 trinitrophenol.
Level 3: Compounds 'B' and 'C'. Both B and C give the
treatment with CHCl/KOH gives twO The sodium
A. Anaromatic compound 'A' on zinc dust. Oxidation of Dgives E having molecular formula CHeO2. ldentify A to F.
same product 'D' when distilled withgives F which may also be obtained by distilling A with zinc dust.
sodalime
Lsalt of Eon heating with formation of acetophenone from phenol.
2.Write the equation of ok 3 kott.
asta tabe
3. How is toluene otbtained from phenol?
4. Phenol reacts with dil. HNO, at low temperature. The products are separated into two beakers.Christine and Zainab
recorded the boilingof the compounds as given in the tables below.
Beaker Boiling point Beaker BoilinBpoint
1 489 K 1 387 K

2 387 K 2 489 K

If beaker 1contains p-nitrophenol and beaker 2 o-nitrophenol, identify the student whose data collection is correct. Give
areason for your answer.
Ether
Level 1:
1. 2- Methoxy -2- methylpropane on heating with Hl would produce
a) Methyl alcohol and sec-propyl iodide b) Methyl iodide and tert-butyl alcohol
c) Methyl iodide and isobutene d) Methyl alcoholand tert- butyl iodide
2..The reaction of (CH3)s C- Br with NaOCH3 produces:
CH; CH,

12) CH,- 0 ( Br (CH--CH, (e) CH--ONa (d) CH ÇH-CHCH;

CH, CH, CH, CH;

3, Assertion (A): An ether is more volatile than an alcohol of comparable molecular mass.
Reason (R): Ethers are polar in nature.
4.Wite the IUPAC name of the given compound:
-mettyl-ffen
CH,-CH-CH,-0-CH,-CH,
CH,
5. The boilingpoint of ethanol is higher than that of methoxymethane. Justify.
Level 2:
follows:
1. Anupam tabulated the time required for the reaction of different halogen halides with diethyl ether as
Halogenhalide HW HY

Time 1min lmin, 45sec 51 seC

Which of the following options correctly identifies the halide ions?

Y= Br dW= Br, X= Ct, Y=}
a) W=I,X= Br, Y= Cl b) W=CE, X=|,Y=Br c) W=I, X =CB,
2Assertion (A): Bond angle in ethers is slightly less than the
tetrahedral angle.
Reason (R): There is a repulsion between the two bulky (-R) groups.
3.Assertion (A): tert-butyl methylether on treatment with Hl at 373K
gives a mixture of methanol and tert-butyl iodide.
mechanism. t l l e SN, Meeh
<Reason (R): The reaction follows SN2 Na OCty
4. How will you convert phenol to anisole? Naot300
anisole.
5. Write the equation of nitration of
p-bromoanisole.
6. Convert anisole to
7. Write the major product in the following equations:
 CHs

CH, Cl + CH,CH, ONa

CH-o-CH,+,+ HI ’ CttGo# tet,I
CH,

8. State the product of the following reactions:

i CH-CH-CH,-0H, +HBi
0CH;
(ii) + HBr
CH;
(ii) (CH,),C-0C,H,
CH,-CH-0-CH,-CH, ",?+? CH,-t-G-H t, He I
Level 3:
1.Explain the mechanism of following reaction:
2CH, CH,-OHCH,CH,--O-CH,--CH,+ HO

n-propyl alcohol and ethyl alcohol in the presence of

2. Toprepare n-propylethyl ether, Kavita heats a mixture of
concentrated sulphuricacid. Is this a good method to prepare the
product? Give reasons to your answer.

CHy-CHa CH-O-gHs
shesymettd notsitale.
Kue atto frfae ztta

Locu
2

CHgCoce
focts
-2n0 A +étree
Anhy Alcg
tlHco