Professional Documents
Culture Documents
1. Acids have much higher boiling points than isomeric esters because :-
(A) Acids form dimers by H–Bonding
(B) Acids are volatile in steam
(C) Ester are non–volatile
(D) Acids can ionise to give protons in aqueous solution
2. Which of the following acids have the lowest pK a value :-
Cl
A
CH3COOC2H5 CH3COOC(CH3)3
B
CH3CONHNH2
CH MgBr
H3O
6. Ethyl acetate 3
Excess
P
C H ( i ) C H MgBr / ether
CH 3COOH+PCl 5 A B
AlCl3
6 6 2 5
C ; product C would be:-
(ii ) H 3 O
C2H5
(A) CH3 C NH.NH2 (B) CH3 C OC2H5 (C) CH3 C ONH.NH2 (D) CH3 C NH2
O N.NH2 O O
OH NH2
17. The reactivities of acid halides (I), anhydrides (II), esters (III) and amides (IV) with nucleophilic reagents follow the
order
(A) I > II > III > IV (B) IV > III > II > I (C) I > III > II > IV (D) III > II > I > IV
18. In the following sequence of reactions
AlCl3 Zn (Hg)
+ CH3CH2COCl A B
conc. HCl, Heat
OH O
OH
(A) OH (B)
OH
(C) (D)
O O O
20. Which of the following orders regarding the base strength of a leaving group in a reaction of an acid derivative
with a nucleophile is correct :
(A) Cl > RCOO > RO (B) Cl > RO > RCOO
(C) RO > RCOO > Cl (D) RO > Cl > RCOO
21. The correct sequence of decreasing order of reactivity of hydrolysis of acid chlorides is :
(A) PhCOCl > p-O 2NC 6H 4COCl > p-CH 3OC 6 H 4COCl
(B) PhCOCl > p-CH 3OC 6H 4COCl > p-O 2 NC 6H 4COCl
(C) p-O 2NC 6H 4COCl > PhCOCl > p-CH 3OC 6 H 4COCl
(D) p-O 2 NC 6H 4COCl > p-CH 3OC 6H 4COCl > PhCOCl
22. Kolbe electrolysis of potassium succinate gives CO 2 and ................. :
(A) C 2H 6 and KOH (B) C 2H 2 and KOH
(C) C2H 4, KOH and H 2 (D) CH 4, C2H 6 and C 2H 4
23. In the following reaction identify compounds A, B, C and D :
PCl 5 + SO 2 A + B ;
A + CH 3 COOH C + SO 2 + HCl
2C + (CH 3) 2 Cd D + CdCl 2
(A) SOCl2, POCl3, CH3COCl, CH3COCH 3 (B) SOCl 2, HCl, CH 3Cl, CH 3CHO
(C) SO2, Cl2, C2H5Cl, CH3COCH3 (D) None of these
24. What are A and B in the following sequence of reactions :
P ( i ) Alc.KOH excess
(i) CH3CH2COOH
Br2
A ; (ii) A (ii ) H
B
Br
Br
(C) CH2CH2COOH, CH2 = CH.COOH (D) H3C——–COOH, H2C=C—COOH
Br Br Br
25. Which of the following compound would be expected to decarboxylates when heated :-
O O O O
(A) (B)
H3C OH H3C CH3
O O O O
CH3 OH
(C) H C (D) H3C
3
O CH2
1. Which of the following reactions involve a decrease in the length of the carbon chain :-
(A) Schmidt reaction (C) Hofmann's bromamide reaction
(C) Hell-Volhard-Zelinski reaction (D) All of these
2. Dry distillation of a mixture of calcium formate and the calcium acetate gives –
HOCH2.CH2OH 1. LiAlH4,Et2O
+ A + B
H 2.H3O
COOCH3
The products (A) and (B) are, respectively,
O OH O
O O
O
CH3OC COOCH3 COOCH3
COOCH3
O
CH2COOH
1. B2H6, THF
+
A
2.HO
3
O2N
CH2CH2OH CH2CH2OH
(A) (B)
O2N H2N
CH2CHO CH2COOH
(C) (D)
O2N H2N
5. Which of the following methods are used for the conversion of carboxylic acids into acid chlorides
(RCOOH RCOCl) ?
(A) RCOOH + SOCl2 (B) RCOOH + PCl5
(C) RCOOH + Cl2 (D) RCOOH + P + Cl 2
6. Which of the following statements are correct for benzoic acid ?
(A) Nitration gives o-and p-nitrobenzoic acid.
(B) Bromination (Br 2/FeBr 3) gives m-bromobenzoic acid.
(C) The Friedel-Crafts reaction with CH 3COCl/AlCl 3 gives m-carboxyacetophenone.
(D) The reaction with concentrated sulphuric acid gives 3-carboxybenzenesulphonic acid.
7. Which of the following compounds react with aniline to give acetanilide :
Which of the following compounds react with aniline to give acetanilide.
O
–NH2 –NHCCH3
Aniline Acetanilide
O O O
(A) CH3COCl (B) H C O CH3 (C) CH3CHO (D) –OCCH3
3
CH3
Br2 1.KCN
A +
B
light 2. H3O ,Heat
CH3 COH
2
CH3 CH2CO2H
CO2H
(A) (B) (C) (D)
CO2H
9. What is compound Z :
NaCN H3O 3 2 CH CH OH
CH3CH 2CH 2Br X Y
H
Z
O
(A) CH3CH=CHCOH (B) CH 3CH 2CH 2CH=NOCH 2CH 3
O
(C) CH3CH2CH2CH(OCH2CH3)2 (D) CH3CH2CH2COCH2CH3
O
CH 3 OH
10. A , A is :
O
(A) CH2—CH2 (B) CH2— CH2 (C) Both are correct (D) None is correct
OH COOCH3 COOH OCH3
Cl
OH H3C
H3C
O
O
O O
OR OH
+ ROH
O
Q u e. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
An s . A ,B A ,B,C C A A,B,D B,D A ,B,D D D A B B C B A ,B,C
Q u e. 16 17 18 19 20
An s . A,D C,D A,B,C A ,B,D A,B,D
EXERCISE–03 MISCELLANEOUS TYPE QUESTIONS
TRUE OR FAL SE :
Red P / X 2
(B) Curtius reaction (q) R–CH2COOH
R–CH–COOH
X
NaN 3
(C) Decarboxylation (r) RCOCl
RNH 2
N3H
(D) HVZ reaction (s) RCOOH
RNH 2
O O OH O
(A) R–C–NH2 (B) R–C–NH3 (C) R–C–NH2 (D) R–C–NH
2
OH
(A) OH (B)
OH OH
HO O
(C) OH (D) OH
Comprehension # 2
Ester gives nucleophilic addition reaction followed by elimination reaction with carbon nucleophile. When
carbon nucleophile is of an ester then the reaction is known as Claisen condensation reaction. This reaction
is also carried out between ester and a ketone. A successful Claisen condensation requires an ester with
two -hydrogens and an equivalent amount of base rather than a catalytic amount of base.
1. Consider the given reaction
C 2 H 5 ONa ester ( X )
CH3–COOC2H5
C 2 H 5 OH
enolate ion
Claisen condensation
Product
O O
|| ||
(A) C6H5COOC2H5 (B) C 2 H 5 O C C OC 2 H 5
O
||
(C) HCOOC2H5 (D) C 2 H 5 O C OC 2 H 5
O
||
C 2 H 5 O C (CH 2 ) 3 CH 2 COOC 2 H 5
(i ) C 2 H 5 ONa / C 2 H 5 OH
[X]
( ii ) H 2 O / HCl
[X] is :
O O O O O
[X] is :
O
|| COOC 2 H 5
(A) H C Cl (B) HCl + CO (C) HCOOC2H5 (D) |
COOC 2 H 5
Comprehension # 3
The reactivity of acid derivatives in general follows the order :
O
R R–C R R
C=O > O> C=O > C=O
Cl R–C RO NH2
O
The above order of reactivity can be explained in terms of the :
(i) Basicity of leaving group (ii) Resonance effect (iii) Inductive effect
Weaker is the basic character of leaving group, more is the reactivity of acid derivative. In general, all the
acid derivatives show resonance as follows:
R R
–
C=O C––O
L
.. L
+
4. Acid derivatives although contain ––C–– group, yet do not undergo the usual properties of carbonyl group.
It is due to:
(A) inductive effect (B) resonance (C) eletromeric effect (D) all of these
5. Which of the following compounds will be most easily hydrolysed ?
(A) Acid halide (B) Acid amide (C) Ester (D) Acid anhydride
Tr u e / Fals e
1. T 2. F 3. T 4. F 5. T
F i ll i n t h e B lanks
1. Benzene 2. pk a= –log k a 3. deactivation , electron withdrawing
4. - Hydrogen, halogen 5. CO2
Matc h th e C o lu mn
1. (A) r ; B s ; (C) p ; (D) q 2. (A) s ; (B) r ; (C) q ; (D) p ; (E) t
3. (A) s ; (B) r ; (C) p ; (D) q
A s s er ti o n - R eas o n Qu es ti o ns
1. C 2. D 3. C 4. C 5. A
C o mp r eh e ns i o n B as ed Qu es ti o ns
Comprehension #1 : 1. (C) 2. (C) 3. (A) 4. (B)
Comprehension #2 : 1. (B) 2. (B) 3. (A) 4. (C)
Comprehension #3 : 1. (A) 2. (A) 3. (B) 4. (B) 5. (A)
EXERCISE–04 [A] CONCEPTUAL SUBJECTIVE EXERCISE
1. Carbon-oxygen bond length in formic acid are 1.23 Å and 1.36Å but in sodium formate both the carbon-
oxygen bonds have same value, i.e., 1.27Å. Explain.
2. The second dissociation constant of fumaric acid is greater than maleic acid. Explain.
3. Which is stronger conjugate base in each pair ?
O O
NaBH 4 H O / H
A
2
B
OH
6. In the following reaction, trace the position of isotopic O18.
O O
18
CH3––C––O––H + CH3CH2––O––H CH3––C––O––CH2CH3 + H2O
7. Write the reagents to carry out following conversions:
O O
II......... I.........
CH3CH CH3CCl CH3CH2OH
O
AlCl3
8. + O A, What is A?
O
(i ) Mg / ether
X Y
9. + NBS (ii )CO 2 ;
(iii )H 3 O
0°C
10. HN + Br2 OH A
1. Formate in shows equivalent resonating structures while formic acid does not.
2. After the first dissociation, maleate ion is more stabilised due to intramolecular H-bonding, whereas fumarate
ion does not have intramolecular H-bonding.
OH O
3
5. A : 5 1
(NaBH 4 reduces keto group)
6 4 2 OH
6
4 5
O
B : 3
1 (by intramolecular esterification)
2 O
O
18
6. O is in ester CH3COCH2CH3
7. I : LiAlH4 II : Pd/BaSO4 (Rosenmund)
O
C
CH2
8. A is formed by Friedel-Crafts reaction A :
CH2
HO— C
9. X : —Br Y : —COOH
O O
0°C
10. HN + Br2 OH Br––N + HBr
O O
1-Bromopyrrolidine-2, 5-dione
or N-Bromosuccinimide (NBS)
Br
H3C
NBS
CH2
CH2
EXERCISE–04 [B] BRAIN STORMING SUBJECTIVE EXERCISE
O
PCl5 H2, Pd/BaSO4 dil. NaOH
CH3COH A B
C
2. When the compound shown was heated in refluxing hydrochloric acid, a compound with the molecular formula
A(C5H6O3) was isolated. Identify this product. Along with this product, three other carbon-containing substances
are formed. What are they ?
O
CH3O COCH(CH3)2
CH3O COCH(CH3)2
O
What happens when A(C 5H 6O 3) reacts with
(A) HCN follwed by hydrolysis (B) soda lime/
(C) NH 2NH 2/glycol, OH – (D) P/Br 2 (E) N 3 H
3. CH 3COO – (acetate ion) is more stable than C 2H5O – (ethoxide ion). Explain.
4. Which is more reactive in each pair towards S N reaction ?
O O
(A) CH3CCl or CH3Cl (B) CNH2 or NH2
O O
(C) CH3COCCH3 or CH3OCH3
H2C C
AlCl3 Zn(Hg) SOCl2 AlCl3
O + A B C
HCl
5. H2C
C
O
+
LiAlH4 H / NBS alcoholic KOH
D E F G H
Identify A to H.
6. O reacts with :
-Butyrolactone (ester)
N3H
8. CH3COOH H2SO4
A
NH3
Reagent
B
COCl
(i) is reduced by LiAlH4.
COCl
O
(ii) is reduced by using LiAlH4 and by using Lindlar's catalyst.
O
H3C O
+
P2O5 H3O Br2/P AgOH
CH––C (A) (B) (C) (D) Diester.
-2H2O
H3C NH2
BRAIN STOR MIN G SUBJ ECTIVE E X ER CISE ANSWER KEY E XE R CISE -4 (B)
O O
1. A : CH3CCl B : CHCH
3 (Rosenmund)
C : CH 3CH=CHCHO (aldol condensation)
Br O
COOH
D : BrC––COH E :
COOH
Br
2. Given compound represents
(i) acetal (ii) ester
When it is subjected to acidic hydrolysis, acetal changes to carbonyl group and ester changes to acid.
O O
O O
–H2O
O
COH
O COOH + CO2 O
COH
A(C5HO
6 3) (Z)
O
(X), (Y) and (Z) are thus, other carbon containing product along with C 5H6O 3 which is the main product.
A(C5H6O3) has (i) keto group (ii) carboxylic group
HO HO
+
HCN H3O
O COOH COOH COOH
(A) NC HOOC
(A)
CaO/NaOH
(B) A
O
NH2NH2
(C) A —COOH (Wolff-Kishner reduction)
glycol, OH
P/Br2
(D) A O COOH (HVZ-reaction)
Br
N3H
(E) A O NH2 (Schmidt-reaction)
–
+
O
3. CH3––C CH3––CH2––O–
–
O
Acetate ion Ethoxide
Electron delocalion, as shown by following resonance structures, causes the negative charge in acetate to
be shared equally by both oxygens. This type of resonance effect is not possible in ethoxide ion.
.. –
..
..
..
O O
.. O
CH3C
..
CH3C
.. CH3C
O O
..
..
.. O
–
O O O O
4. (A) CH3CCl (B) CNH2 (C) CH3COCCH3
O O
H2C C C
AlCl3 Zn(Hg) SOCl2
O + HCl
H2C C C C
5. C
OH O OH O Cl O
O
(A) (B) (C)
+
AlCl3 LiAlH4 H / NBS
-H2O allylic substitution
O OH
(D) (E) (F)
Br
alcoholic KOH
(G) (H)
O
NH3 CH2CH2CH2C=O
6. (A) O OH NH2
-butyrolactone alcohol amide
O
LiAlH4 CH2CH2CH2CH2
(B) O
OH OH
alcohol alcohol
O
+
EtOH/H CH2CH2CH2COEt
(C)
O (transesterification)
OH O
alcohol ester
O
NaBH4/EtOH
(D) No reaction (ester is not reduced by NaBH 4).
O
7. In case of carbonyl compounds H – or R – are poor leaving group , therefore addition take place.
But in case of acid derivatives, Z– are good leaving group therefore subsitution take palce.
O
8. (i) A : CH 3—NH 2 B : CH3—C—NH2
(ii) Reagent =Br 2 /Alc. KOH
O OH
COCl CH2OH
9. (i) LiAlH4
+ [H]
COCl CHO
O O
Pd/BaSO4
(ii) + H2 Boiling xylene
O O
CH2OH
[H] CH2OH
LiAlH4 OH
O
H3C OH H3C O C CH3
AgOH
CH C C
H3C –2H2O H3C CH3
COOH C O
O
(D)
Diester
EXERCISE–05 PREVIOUS YEARS QUESTIONS
OCOCH3
P CH3 Acidic
11. Product
Hydrolysis
OCOCH3
H3C Q
CHO
13. Compound (A) C5H8O2 liberated CO2on reaction with sodium bicarbonate. It exists in two forms neither of
which is optically active. It yielded compound (B). C5H10O2 on hydrogenation. Compound (B) can be separated
into enantiomorphs. Write structures of (A) and (B). [IIT -87]
14. An organic compound (A) on treatment with acetic acid in presence of sulphuric acid produces an ester (B).
(A) on mild oxidation gives (C). (C) with 50% KOH followed by acidification with dilute HCl generates (A) and
(D). (D) with PCl5 followed by reaction with ammonia gives (E). (E) on dehydration produces hydrocyanic acid.
Identify (A) to (E) [IIT -87]
15. Compound (A) (C6H12O2) on reduction with LiAlH4 yielded two compounds (B) and (C). The compound (B) on
oxidation gave (D). 2 moles of (D) on treatment with alkali (aqueous) and subsequent heating furnished (E).
The later on catalytic hydrogenation gave (C). The compound (D) was oxidized further to give (F) which was
found to be monobasic acid (m.wt. 60.0). Deduce structures of (A) to (F). [IIT -90]
16. The sodium salt of a carboxylic acid, (A) was produced by passing a gas (B) into aqueous solution of caustic
alkali at an elevated temperature and pressure (A) on heating in presence of sodium hydroxide followed by
treatment with sulphuric acid gave a dibasic acid (C). A sample of 0.4g of (C) on combustion gave 0.08g of
H2O and 0.39g of CO2. The silver salt of the acid, weighing 1.0g, on ignition yielded 0.71 g of Ag as residue.
Identify (A), (B) and (C). [IIT -90]
17. Two mole of an ester (A) are condensed in presence of sodium ethoxide to give a -keto ester (B) and
ethanol. On heating in an acidic solution (B) gives ethanol and - keto acid (C). On decarboxylation (C) gives
3-pentanone. Identify (A), (B) and (C) with proper reasoning and give reactions. [IIT -92]
18. An organic compound A(C4H6O3) on treatment with ethyl alcohol gives a carboxylic acid B and compound C.
Hydrolysis of C under acidic conditions gives B and D. Oxidation of D with KMnO4 also gives B. B on heating
with Ca(OH)2 gives E (Molecular formula C3H6O) E does not gives Tollen's test and does not reduce Fehling
solution but forms 2,4–dinitrophenylhydrazone. Identify A to E. [IIT -92]
19. An acidic compound (A), C4H8O loses its optical activity on strong heating yielding (B). C4H6O2 which reacts
readily with KMnO4. (B) forms a derivative (C) with SOCl2, which on reaction with CH3NH2 gives (D). The
compound (A) on oxidation with dilute chromic acid gives an unstable compound (E) which decarboxylate
readily to give (F), C3H6O. The compound (F) gives a hydrocarbon (G) on treatment with amalgamated Zn
and HCl. Give structures of (A) to (G) with proper reasoning. [IIT -95]
20. An liquid (X) having molecular formula C6H12O2 is hydrolysed with water in presence of an acid to give a
carboxylic acid (Y) and an alcohol (Z). Oxidation of (Z) with chromic acid gives (Y). What are (X), (Y) and (Z).
[IIT -96]
21. Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric oximes. Write
structures of the oximes. [IIT -97]
22. An organic acid (A), C5H 10O2 reacts with Br2 in the presence of phosphorus to give (B). Compound (B)
contains an asymmetric carbon atom and yields (C) on dehydrobromination. Compound (C) does not show
geometric isomerism and on decarboxylation gives an alkene (D) which on ozonolysis gives (E) and (F).
compound (E) gives a positive schiff's test but (F) does not. Give structures of (A) to (F) with reasons.
[IIT -97]
23. The correct IUPAC name of C6H5COCl is
(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone [IIT 2006]
24. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product? [IIT 2006]
25. Identify the binary mixtures (s) that cna be separated into the individual compounds, by differential extraction,
as shown in the given scheme - [IIT 2012]
NaOH(aq)
Compound 1 + Compound 2
Binary mixture containing
Compund 1 and compound 2
NaHCO3(aq)
Compound 1 + Compound 2
O O
1. H3 O ,
O
2. O3
P
3. H2 O2
O
O
P RE VIOU S Y EARS QU E STION S ANSWER KEY E XE R CISE -5
H
*
(B) CH3.CH2.C–COOH (2-methylbutanoic acid)
CH3
1 4 . A = CH3OH (Methanol)
B = CH3COOCH3 (Methyl ethanoate)
C = HCHO (Methanal)
D = HCOOH (Methanoic acid)
E = HCONH2 (Formamide or methanamide)
1 5 . (A) CH3COOCH2CH2CH2CH3
(B) C2H5OH
(C) CH3CH2CH2CH2OH
(D) CH3CHO
(E) CH3CH=CHCHO
(F) CH3COOH
H CH3
H3C OH H3C
D = H2C N E= F=
O O O
CH3
O
CH3
G = H3C
O
H3C
H3C CH3 O
20. X = O Y =
HO
propyl propionate
Propionic acid
H3C
Z= OH
propan-1-ol
H3C H3C OH N N
OH HO
syn anti (isomers)
H3C Br H3C
H3C
22. A = C=
B=
O H3C O
H3C H3C O
HO HO
HO
H3C
H3C
O
D = CH2 E = HCHO F=
H3C
H3C
23. C 24. C 25. B, D 26. (2)
EXERCISE # JEE MAIN
ALL QUESTIONS BASED ON
HALOGEN & OXYGEN CONTAINING ORGANIC COMPOUND
1. Following reaction :
(CH3)3C–Br + H2O (CH3)3C–OH + HBr
is an example of- [AIEEE-2002]
(A) Elimination reaction (B) Free radical substitution
(C) Nucleophilic substitution (D) Electrophilic substitution
1
2. SN reaction is easible in- [AIEEE-2002]
Cl
(A) Cl + KOH (B) + KOH
3. Bottles containing C6H5I and C6H5–CH2I lost their original labels. They were labelled A and B for testing. A
and B were separately taken in a test tube and boiled with NaOH solution. The end solution in each tube was
made acidic with dilute HNO3 and then some AgNO3 solution was added. Substance B gave a yellow precipitate.
Which one of the following statements is true for this experiment. [AIEEE-2003]
(A) A was C6H5I (B) A was C6H5CH2I
(C) B was C6H5I (D) Addition of HNO3 was unnecessary
4. The reaction of chloroform with alcoholic KOH and p-toluidine form- [AIEEE-2003]
5. The compound formed on heating chlorobenzene with chloral in the presence of concentrated sulphuric acid
is- [AIEEE-2004]
(A) Gammaxe (B) DDT
(C) Freon (D) Hexa chloro ethane
6. Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH is-
[AIEEE-2006]
(A) CH3CH2CH(OH)CH2CH 3 (B) C 6H 5CH 2CH 2OH
CH3
(C) H3C (D) PhCHOHCH3
OH
7. The structure of the major product formed in the following reaction is : [AIEEE-2006]
Cl
NaCN
DMF
I
CN CN Cl CN
(A) (B) (C) (D)
NC
CN CN I
8. Which of the following on heating with aqueous KOH, produces acetaldehyde ? [AIEEE-2009]
(A) CH2ClCH2Cl (B) CH3CHCl2 (C) CH3COCl (D) CH3CH 2Cl
9. Maximum dehydration takes place that of - [AIEEE-2002]
OH
COOH COOH NO2 COOH
NO2
11. An ether is more volatile than an alcohol having the same molecular formula. This is due to -
[AIEEE-2003]
(A) Inter molecular hydrogen bonding in ethers (B) Inter molecular hydrogen bonding in alcohols
(C) Dipolar character of ethers (D) Alcohols having resonance structures
12. When CH2 = CH–COOH is reduced with LiAlH4, the compound obtained will be - [AIEEE-2003]
(A) CH3–CH2–CH2OH (B) CH3–CH2–CHO (C) CH3–CH2–COOH (D) CH 2=CH–CH 2OH
13. The general formula CnH 2nO2 represents [AIEEE-2003]
(A) Diols (B) Dialdehydes (C) Diketones (D) Carboxylic acids
14. Which one of the following undergoes reaction with 50% sodium hydroxide solution to give the corresponding
alcohol and acid ? [AIEEE-2004]
(A) Phenol (B) Benzaldehyde (C) Butanal (D) Benzoic acid
15. Among the following compounds which can be dehydrated very easily is - [AIEEE-2004]
OH
(A) CH3CH2CHCH
2 2CH2OH (B) CH3CH2CH2CHCH3
CH3
(C) CH3CH2C CH2CH3 (D) CH3CH2CH CH2CH2OH
OH CH3
16. p-cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to
form, the compound B. The later on acidic hydrolysis gives chiral carboxylic acid. The structure of the carboxylic
acid is - [AIEEE-2005]
CH3 CH3
CH(OH)COOH
(A) (B)
CH(OH)COOH
OH OH
CH3
CH3
CH2COOH
(C) (D)
CH2COOH
OH
OH
17. HBr reacts with CH2 = CH – OCH3 under anhydrous conditions at room temperature to give -
(A) BrCH2CHO and CH3OH (B) BrCH2–CH2–OCH3 [AIEEE-2006]
(C) H3C–CHBr–OCH3 (D) CH3CHO and CH3Br
18. The structure of the compound that gives tribromo derivative on treatment with bromine water is -
[AIEEE-2006]
Me Me
Me Br Me
Br Br
A B C
OH OH OH OH
; ; ;
CH2Br
CH2Br C2H5 CH2Br
(A) (B) (C) (D)
Br CH3
CH 3 CH 3
42. An organic compound A upon reacting with NH3 gives B. On heating, B gives C. C in presence of KOH reacts
with Br2 to give CH3CH2NH2. A is :-
(A) CH3COOH (B) CH3CH2CH 2COOH
43. An unknown alcohol is treated with the "Lucas reagent' to determine whether the alcohol is primary, secondary
or tertiary. Which alcohol reacts fastest and by what mechanism :-
(A) secondary alcohol by SN1 (B) tertiary alcohol by SN1
(C) secondary alcohol by SN2 (D) tertiary alcohol by SN2
Q u e. 1 2 3 4 5 6 7 8 9 10 11 12 13
Ans B C B D D B C A B C B D D
Q u e. 14 15 16 17 18 19 20 21 22 23 24 25 26
Ans B C A D D Bonus D D B C C B A
Q u e. 27 28 29 30 31 32 33 34 35 36 37 38 39
Ans D B C B B C A,C B C A
Q u e. 40 41 42 43
Ans C D D B