24

rganic Compounds
ContainingOxygen
TOPIC 1 In the light of the above 05 CH,CH,CH--CH, Hz0.H,0,,OH
statements, choose the most
Alcohols and Phenols appropriate answer from the what is Z? [NEET (Oct.)2020]
options given below. (a)CH,CH,CH,CH,0H
01 Given below are two statements.
Statement I The acidic strength of
(NEET 2022]
(a) Both statement I andstatement II
(o)CH,CH, GHCH;
monosubstituted nitrophenol is are incorrect. OH
higher than phenol because of (b) Statement | is correct but (c)CH,CH,CH,CHO
electronwithdrawing nitro group. statement l is incorrect. (d)CH,CH,CH,CH,
(c) Statement Iis incorrect but
Statement ll o-nitrophenol, statement llis Correct. 06 The structure of intermediate Ain
M-nitrophenol andp-nitrophenol will (d) Both statement Iand statement ll the following reaction, is
have same acidic strength as they are correct. [NEET (National) 2019]
have one nitro group attached to .CH3
CH OH
the phenolic ring. 03 The major product formed in CHs
in the light of the above statements, dehydrohalogenation reaction of
choose the most appropriate 2-bromo pentane is pent-2-ene. |+ H3C CHs
answer from the options given This product formation is based
beiow. on [NEET 2021] CH3
[NEET 2002] (a) Saytzeff's rule (a) HzC00H
(a) Both statement Iand statement ll are (b)Hund's rule
incorrect. (c) Hoffmann rule
(b) Statement i is correctbut statement lI (d) Huckel's rule
is incorrect.
(c) Statement I is incorrect but statement 04 Which of the following
| is correct. (b)
(d) Both staterTent Iand statement ll are substituted phenols is the
Correct. strongest acid? CH
(NEET (0ct.) 2020]
02 Giyen below are twO statements.
OH CH ooH
Statementiin Lucas test, primary.
secondary and tertiary alcohols are HC
(a (b)
distinguished on the basis of their CH3
reactivity with conc.HCI+ ZnClz! ÖCH
known as Lucas reagent.
OH OH CH3
Statement Il Primary alcohols are CH
most reactive and immediately (d)
produce turbidity at room CH3
temperature on reaction with Lucas CH3 (d)
reagent.
organic
Compounds Containing Oxygen 201
07 The reaction
that
henzoic acid as thedoes
major
not give 11 Compound A, CaH,0, is found to I. CH,CH,0H+HCI anh.ZnC,
is product
[NEET (Odisha) 2019) react with NaOl(produced by I1. CH,CH,OH+HCI’
CH,OH reacting Ywith NaOH) and yields a I. (CH,),COH+HCI
a
yellow precipitate with IV. (CH,), CHOH+HCI anh.ZnClz
characteristic smell.
(a)|, Illand IV
COCH, () NaOCI
Aand Yare respectively.
(b)l and I
(b [NEET 2018]
(in) Ho (c) Only IV
CH,OH
(a
-ÇH-CH, and l, (d) lland IV
(C PCC OH
16 Which of the following is not the
(Pyridin1um (b
CH,OH
chlorochromate) -CH,-CH,-0H and l, product of dehydration of
(d) KMnO,H ?
(c) H,C -CH-0H and l, OH

08 The hydrolysis reaction that takes CH3

[AIPMT 2015)
place at the slowest rate, among (d) CHy -OH and I,
the following is
(NEET (Odisha) 2019] (a (b)
12 Which one is the most acidic
aq.Na0H
(a) compound? [NEET 2017]
OH OH
CH,
-ONa (d)
(a) (b)
CH,
ag. Na0H 17 Which of the following will not be
CH3
(b) H,C-CH,CI soluble in sodium hydrogen
H,C--CH,-0H OH OH carbonate?
aq. Na0H 0,N NO, [AIPMT 2014)
(c) H,C= CH-CH,CI (a) 2,4,6-trinitrophenol
(c) (d)
aq.NaOH
(b)Benzoic acid
(d CH,Ci (c)o-nitiophenol
NO NO2 (d)Benzenesulphonic acid
-CH,0
13 Which of the following reagents 18 In the following sequence of
would distinguish cis-cyclopenta-1, reactions,
09 When vapours of a secondary 2-diol from the trans-isomer?
alcohol is passed over heated
product (a) 0zon
[NEET 2016, Phase I) CH-Br KuN, A HO8.
the end product Cis
LIAIHa,C
ether

Copper at 573 K, the

[NEET (Odisha) 2019] (b) MnO2 [AIPMT 2012]
formed is (c) Aluminium isopropoxide (a) acetone
(a) a carboxylic acid (d) Acetone (b) methane
(b) an aldehyde (c) acetaldehyde
(c) a ketone 14 Reaction of phenolwith chloroform (d)ethyl alcohol
(d) an alkene in the presence of dilute sodium
treatment with hydroxide finally introduces, which 19 In the following reaction,
10 The Compound Aon one of the following functional CH,
with PCl, gives C. B [AIPMT 2015]
Nà gives B,andtogether to give diethyl group? HOH*
and C react (a)- CHCI (b)-cOOH H,CC-CH=CH,
Care in the order (d)-CHO
ether. A.Band [NEET 2018] (c)- CHCi,
CH,
A B
la) C,H,CI, C,H. Czt0H 15 Whichof the following reaction(s) Major product Minor product
C,H,ONa can be used for the preparation of
tb) C,4OH, C,H,C!, alkyl halides? (AIPMT 2015]
[AIPMT 2012)
{cj CH,0H,C,H, CzH,CI
CzHCI
tgjC,4OH, C,HONa.
202 NEET Chapterwise Topicwise Chemistry
CH3
CH, 25 H,COH-CH,OH on heating with
(a) H3CÇ-CH-CH3
(a)CHC=CH--CH;and periodic acid gives
OH H3 CH, [AIPMT 2009]
CH3 (a)2C0, (b)2HCO0H
CH, --C-CH,--CH, CHO
(b) ÇH2Ç-CH2 CH3 (c) (d) 2
Br CHO
OH CHs CH,
CH3 26 Consider the following reaction,
(b)CH,C-CH-CH, and Phenol
(c) HC CH, Aik.
CH,CI
HOH CH-CH-CHCH,
Zn -dust, X
Anhy. AICi3 KMnO4Z
Br The product Z is [AIPMT 20091
(Þ) HgC-CHzCH2 CH, (a)toluene (b) benzaldehyde
(c) benzoic acid (d) benzene
CH3 OH (c)CH,-C=CH,-CH, and
CH3 27 Ethylene oxide when treatedwith
20 Which one is a nucleophilic Grignard reagent yields [AIPMT 2006]
CH--C- CH,-CH, (a) secondary alcohol
substitution reaction among the
Br (b) tertiary alcohol
following? [AIPMT 2011]
CH, (c) cyclopropyl alcohol
(a) RCHO+ R'MgX ’R (d) primary alcohol
(d)CH, =-CH,--CH, and
OH 28 The general molecular formula, which
CH, CH;
represents the homologous series of
(b)CH;-CH,-CH--CH,-Br CH,-CH--CH,CH; alkanols is [AIPMT 2006]
+NH, CH-CH, Br (a) C,H02 (b) C,Hz0
(c) CHHn0 (d) C,Hzn+20
CH-CH,-NH 22 Given are cyclohexanol (I), acetic 29 Which one of the following
acid (),2,4, 6-trinitrophenol(1)
(c)CH,CHO +HCN CH,-CH(OH)CN compounds is most acidic ?
and phenol (IV). In these, the order [AIPMT 2005]
(d) CH,CH=CH, + H,0 of decreasingacidic character will
be -OH
[AIPMT 2010]
CH,-CH-CH, (a)ll> |> V>| (b)l|>||>|>V (a) CiCH2-CH,0H (b)
OH (c)ll> |I|> |V>| (d)|ll> IV> l|>| NOz
OH OH

21 In the following reactions, 23 Which of the folowing reactions (c) (d)

[AIPMT 2011] willnot result in the formation of CHz
CH, carbon-carbon bonds? [AIPMT 2010]
(a) Reimer-Tiemann reaction 30 The enzyme which hydrolysis
1. CH,-CH-CH-CH
H /Heat
(b)Cannizaro reaction triglycerides into fatty acids and
(c)Wurtz reaction glycerol is called [AIPMT 2004]
OH (d) Friedel-Crafts's acylation (a) maltase (b) lipase
+ B (c)zymase (d) pepsin
Major
product
Minor 24 Consider the following reaction,
product 31 Which of the following will not form
Ethanol PBr 33XAlc. KOH y
I. A. HBr, dark a yellow precipitate on heating with
inabsence of peroxide (0)H,SO,roomtemperature an alkaline solution of iodine?
C D (ii) H,0, heat [AIPMT 2004]
(Major (Major
The product Z is [AIPMT 2009) (a) CH,CHIOH)CH,
(product product J
the major products A
and Care (a)CH,-CH, (b)CH,CH,0CH,CH, (b) CH,CH,CHOH)CH,
(c) CH,0H
respectively (c)CH,CH,0S0,H (d)CH,CH,0H (d) CH,CH,0H
organic Compounds
Containing Oxygen 203
22 The -OH group of
an
of a alcohol the
-C0OH or 38 The correct acidic order of following
group
can be replaced carboxylic acid is
43 What is formed when a primary
by-Cl using [AIPMT 2001] alcohol undergoes catalytic
[AIPMT 2004]
(a) phosphorus pentachloride OH OH OH dehydrogenation?
[AIPMT 1993]
(b) hypochlorous acid (a) Aldehyde (b)Ketone
(c) chlorine () (c) Alkene (d) Acid
(d)hydrochloric acid
44 Which one of the following on
33 When phenol is CH3 NO2
treated with CHCI,
and NaOH, the product (a) |> ||> |l|
oxidation gives a ketone?
(b) II| >|>|| (a) Primary alcohol [AIPMT 1993]
formed is (c) || > |l >| (d) l> ||>|| (b)Secondary alcohol
(a) benzaldehyde [AIPMT 2002]
(c) Tertiary alcohol
(b)salicylaldehyde 39 The ionisation constant of phenol is (d) All of the above
(c) salicylic acid higher than that of ethanol because
(d)benzoic acid [AIPMT 2000] 45 Increasing order of acidic strength
(a) phenoxide ion is bulkier than among p-methoxy phenol (),
ethoxide p-methyl phenol (I) and
34 n-propyl alcohol and iso0-propyl (b) phenoxide ion is stronger base than
alcohol can be chemically p-nitrophenol (l) is
ethoxide [AIPMT 1992]
distinguished by which reagent? (c) phenoxide ion is stabilised through
(a) lll, 1, | (b)||, 1, | (c) I, I, I (d)I, 1, I
[AIPMT 2002] delocalisation
la) PCk (d) phenoxide ion is less stable than 46 When phenol is treated with excess
(b) reduction ethoxide of bromine water., it gives
(c) oxidation with potassium [AIPMT 1992]
dichromate
40 Propan-1-ol may be prepared by (a) m-bromophenol
reaction of propene with (b)o- and p-bromophenols
(d) ozonolysis
[AIPMT 2000] (c) 2,4-dibromophenol
35 In preparation of alkene from (d) 2,4,6-tribromophenol
alcoholusing Al,03, which is (a) CH 47 Methanol is industrially prepared by
effective factor? (b)H,B0, [AIPMT 1992]
[AIPMT 2001] (c) B,H, /NaOH-H,0, (a) oxidation of CH, by steam at 900°c
(a) Porosity of Al,03 (d)H,S0,/ H,0 (b) reduction of HCHO using LiAlH,
(b) Temperature (c) reaction of HCHO with a solution of
(c)Concentration 41 Reaction of H, CCH, with RMgX NaOH
(d) reduction of CO usingH, and
(d) Surface area of Al,0,
Zn0- Cr,0,
leads to formation of
36 Which of the following is correct? [AIPMT 1998]
[AIPMT 2001] 48 How many isomers of CçH,OH wil
(a) RCHOHR (b) RCHOHCH,
(a) Cycloheptane is an aromatic R be primary alcohols?
compound [AIPMT 1992]
(c) RCH,CH,0H (d) CHCH,0H (a)5 (b)4
(b) Diastase is an enzyme
R (c)2 (d)3
(c) Acetophenone is an ether
(d) All of the above
42 The boiling point of p-nitrophenol is 49 Propene, CH-- CH=CH, can be
is higher than that of o-nitrophenol
37 Which one of the following
[AIPMT 2001]
converted into 1-propanol by
Correct? because [AIPMT 1994) oxidation. Indicate which set of
(a) Reduction of any aldehyde
gives (a) NO, group atp-position behaves in a reagents amongst the following is
secondary alcohol different way from that at o-position ideal to affect the above
oil with H,SO, (b) intranmolecular hydrogen bonding
(b) Reaction of vegetable exists in p-nitrophenol
Conversion? [AIPMT 1989]
gives glycerine (a)KMnO, (alkaline)
gives (c) there is intermolecular hydrogen
lc) Alcoholic iodine with NaOH bonding in p-nitrophenol (b)Osmium tetroxide (Os0, / CH,Ci,)
iodoform NaCl gives (d) p-nitrophenol has a higher molecular (c)B,Hg and alkH,0,
Sucrose on reaction with
d) is a paleyellow weight than o-nitrophenol (d)0,/Zn
invert sugarlodoform
soiid.