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Aldehydes Ketones, Carboxylic Acids
Aldehydes Ketones, Carboxylic Acids
Sol: (2) Acetaldehyde react with tollen's reagent while ketone do not react with tollen's reagent.
3. Which of the following will react with water
(1) CHCl 3 (2) Cl 3 CCHO (3) CCl 4 (4) ClCH 2 CH 2 Cl
Sol: (2) C C l 3 C H O H 2 O C C l 3 C H ( O H )2
( C h lo r a l h yd r a te )
4. An organic compound ‘A’ has the molecular formula C 3 H 6 O, it undergoes iodoform test. When saturated
with dil. HCl is gives ‘B’ of molecular formula C 9 H 14 O . A and B respectively are
Compound B having carbon atoms three times, the number of carbon atoms in propanone, it
is 2, 6-dimethyl-2, 5-heptadien-4-one.
5. Which alkene is formed from the following reaction CH 3 CH 2 CH 2 CH PPh 3 2 Butanone
[O ]
Sol: (1) CH 3 CH 2 CH 2 OH CH 3 CH 2 CHO
(A) (B)
H
|
HCl
CH 3 CH 2 C O H 2 NNHCONH 2 CH 3 CH 2 CH N NHCONH 2
(4) On oxidation with alkaline KMnO 4 followed by hydrolysis gives benzoic acid
Sol: (2) Acetophenone is a ketone and does not react with Tollen’s reagent to give silver mirror.
8. The enol form of acetone, after treatment with D 2 O, gives
OD O OH OD
| || | |
(1) CH 3 C CH 2 (2) CD 3 C CD 3 (3) CH 2 C CH 2 D (4) CD 2 C CD
O OH OD OD O
Sol: (2) ||
|
| | ||
CH 3 C CH 3 C H 3 C CH 2 CH 3 C CH 2 CH 3 C CH 2 CH 3 C CH 2D
A c et o n e ( k e t o f o r m ) e n o l fo rm
OH OD O O
| | || ||
C H 2 C C H 2 D D 2O C H 2 C C H 2 D D C H 2 C C H 2 D D 3C C C D 3
The enol form of acetone on treatment with D2 O undergoes enolisation, deutration (addition of D2 O )
and dehydration (removal of H 2O ). The repeated enolisation, deutration and dehydration ultimately
gives CD 3 . COCD 3 (B) . O
Sol: (2) Both Zn(Hg ), HCl and NH 2 NH 2 , OH can reduce COCH 3 group to CH 2 CH 3 group, but HCl
will also bring about dehydration of alcohol to form alkene. Therefore, appropriate reagent
for the conversion is NH 2 NH 2 , OH .
10. Which of the following has the most acidic hydrogen
(1) 3-hexanone (2) 2, 4-hexanedione (3) 2, 5-hexanedione (4) 2, 3-hexanedione
Sol: (2) 2, 4-hexanedione (a 1, 3-diketone) has the most acidic hydrogen. This is because the
carbanion left after the removal of H is resonance stabilised in this case.
O O O O
|| || || ||
OH
CH 3 C CH 2 C CH 2 CH 3 CH 3 C C H C CH 2 CH 3
2, 4 Hexanedion e H 2O
O O O O O O
|| || | || || |
CH 3 C C H C CH 2 CH 3 CH 3 C CH C CH 2 CH 3 CH 3 C CH C CH 2 CH 3
11. Which of the following will be most readily dehydrated in acidic conditions
O OH OH
(1) (2)
O O
(3) OH (4) OH
Sol: (1) Aldols (-hydroxy aldehydes or -hydroxyketones) readily undergo dehydration to form ,
O OH O
-Hydroxyketone O
(A)
CHO
12.
Major Product is
CHO
COOH
HO
(1) (2)
COOH HOOC
O COOH
O
CH2OH
(3) (4)
O
O
CH2OH
Sol: (2)
CHO CHO
CHO CHO
CHO
COOH
COOH
13. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(1) MeCOCl (2) MeCHO (3) MeCOOMe (4) MeCOOCOMe
Sol: (1) Amongst aldehyde & the acid derivatives, acid chloride are the most susceptible to
nucleophilic attack due to strong –I effect & weak +R effect of the Cl-atom as a result of
which carbonyl carbon has the highest electron deficiency. The actual order is
MeCOCl >MeCOOCOMe >MeCOOMe >MeCHO.
14. Which of the following will give yellow precipitate with I 2 / NaOH
(1) ICH 2 COCH 2 CH 3 (2) CH 3 COOCOCH 3 (3) CH 3 CONH 2 (4) CH 3 CH (OH )CH 2 CH 3
I / NaOH
Sol: (1,4) 2
ICH2 COCH 2CH 3
CHI 3 CH 3 CH 2 COONa
I2
CH 3 CH CH 2CH 3
CH3CH2COONa CHI3
| NaOH
OH
Q=
(1) Lucas Reagent (2) 2,4-DNP (3) Fehling’s Solution (4) NaHSO 3
O
H 2O / H OH
Sol: (3) P H 2 C H 3C
H O / H
Q 2
H 3 C
OH ⇌
CHO
Ketone (non-reducing) and aldehyde (reducing) can be distinguished by Fehling solution.
16. On vigorous oxidation by permanganate solution (CH 3 )2 C CH CH 2 CH 2 CH 3 gives
OH OH
| |
(1) CH 3 C CH CH 2 CH 3 (2) (CH 3 )2 C H C O O H C H 3 C O O H
|
CH 3
Sol: (4) C H 3 C C H C H 2C H 2C H K
M nO4
CH 3
C O H O O C C H 2C H
3 3
CH 3 CH 3
Heat
(3) o CH 3 C 6 H 4 COC 6 H 5 (4) both 1 and 2
AlCl3
Sol: (2) C6 H6 C6 H 5 COCl C6 H 5 COC6 H 6 HCl
Sol: (4) Aldehyde & ketone are colourless & stable compound
19. Which of the following statements regarding chemical properties of acetophenone are wrong
(1) It is reduced to methyl phenyl carbinol by sodium and ethanol
(2) It is oxidised to benzoic acid with acidified KMnO 4
(3) It does not undergo iodoform electrophilic substitution like nitration at meta position
(4) It does not undergo iodoform reaction with iodine and alkali
(1) 1 and 2 (2) 2 and 4 (3) 3 and 4 (4) 1 and 3
Sol: (3) It undergoes electrophilic substitution at m-position and also gives iodoform test.
20. The product(s) obtained via oxymercuration (HgSO 4 H 2 SO 4 ) of 1-butyne would be
(1) CH 3 CH 2 COCH 3 (2) CH 3 CH 2 CH 2 CHO (3) CH 3 CH 2 CHO HCHO (4) CH 3 CH 2 COOH HCOOH
OH O
| keto - enol ||
Sol: (1) CH 3 CH 2 C CH H 2O CH 3 CH 2 C CH 2 CH 3 CH 2 C CH 3
But 1 yne tautomeris m Butan 2 one
21. The most reactive compound towards formation of cyanohydrin on treatment with KCN followed by
acidification is
(1) Benzaldehyde (2) p-Nitrobenzaldehyde
(3) Phenyl acetaldehyde (4) p-Hydroxybenzaldehyde
Sol: (2) Due to electron withdrawing nature of NO 2 group, the partial +ve charge on the carbon
atom of the C O group in p-nitrobenzaldehyde increases and hence becomes more susceptible
to nucleophilic attack by CN ion.
22. The key step in cannizzaro’s reaction is the intermolecular shift of
(1) Proton (2) Hydride ion (3) Hydronium ion (4) Hydrogen bond
Sol: (2) Cannizzaro reaction is an example of hydride ion (H ) transfer reaction.
23. Benzophenone does not react with
(1) RNH 2 (2) SO 3 (3) NaOH (4) Na 2 CO 3
24. The most suitable reagent for the conversion of RCH 2 OH RCHO is
(1) KMnO 4 (2) K 2 Cr 2 O 7 (3) CrO 3 (4) PCC
Sol: (4) The alcohol can be converted to aldehyde group by treating with oxidising agent
Pyridinium chloro chromate (C6 H 5 N HCrO 3 Cl ) it is abbreviated as PCC and is called Collin's
reagent. This reagent is used in non aqueous solvent like CH 2 Cl 2 It is a very good reagent
because it checks the further oxidation of aldehyde to carboxylic acid while rest oxidising
agent oxidise aldehyde into carboxylic acid.
25. The conversion of acetophenone to acetanilide is best accomplished by using :
(1) Backmann rearrangement (2) Curtius rearrangement
(3) Lossen rearrangement (4) Hofmann rearrangement
CH 3 CH 3
| |
H 2 SO 4
Sol: (1) C6 H 5 C O H 2 NOH C6 H 5 C NOH
H O 2
C 6 H 5 NHCOCH 3
Acetopheno ne oxime or Backmann Acetanilid e
methyl phe nyl ketoxime rearrangem ent
iodoform test.
CH COONa
27. MeO 3
CHO ( X ) CH CHCOOH The compound (X) is
H3O
(1) CH 3 COOH (2) BrCH 2 COOH (3) (CH 3 CO ) 2 O (4) CHO COOH
(1) OH (2)
OH
(3) (4)
Sol: (2)
( 2 )Zn / H O 2
32. The reagent(s) which can be used to distinguish acetophenone from benzophenone is (are)
(1) 2, 4-dinitrophenyl hydrazine (2) Aqueous solution of NaHSO 3
(3) Benedict reagent (4) I2 and Na 2 CO 3
Sol: (4) Acetophenone gives iodoform reaction while benzophenone does give this.
33. When acetaldehyde is heated with Fehling solution, it gives a red precipitate of
(1) Cu (2) CuO (3) Cu 2 O (4) Cu (OH ) 2
2
Sol: (3) CH 3 CHO 2
Cu
CH 3 COO Cu2 O 3 H 2 O
5OH
Fehling solution Red ppt.
34. The general order of reactivity of carbonyl compounds for nucleophilic addition reactions is
(1) H 2 C O RCHO ArCHO R 2 C O Ar 2 C O (2) ArCHO Ar 2 C O RCHO R 2 C O H 2 C O
(3) Ar2 C O R 2 C O ArCHO RCHO H 2 C O (4) H 2 C O R 2 C O Ar2 C O RCHO ArCHO
Sol: (1) The size of the alkyle group. Causes hindrance to attacking group. As the number and size
of the alkyl groups incirease the hindrance to the attack of nucleophile also increases. Thus
the reactivity follows the order H 2 C O RCHO ArCHO R 2 C O Ar2 C O .
35. Which of the following gives an alcohol and salt of carboxylic acid when reacted with conc. NaOH
(1) CH 3 CHO (2) C 6 H 5 CHO (3) CH 3 COCH 3 (4) C 6 H 5 COCH 3
Sol: (2) Benzaldehyde does not have the -hydrogen so it will undergoes cannizzaro’s reaction.
NaOH
2C 6 H 5 CHO C 6 H 5 CH 2 OH C 6 H 5 COONa
36. Which of the following compounds would undergo Cannizzaro's reaction
(1) Propionaldehyde (2) Benzaldehyde (3) Bromobenzene (4) Acetaldehyde
Sol: (2) C 6 H 5 CHO Aldehydes – Those aldehyde in which H atom is absent can participate in
Cannizzaro’s reaction.
37. NaOH / H reacts with
O
||
(1) C 6 H 5 OCH 3 (2) CH 3 OH (3) CH 3 C CH 3 (4) C 2 H 5 OH
OH O
| ||
dil NaOH
Sol: (3) 2CH 3 CO CH 3 CH 3 C CH 2 C CH 3
| (Diacetone alcohol)
CH 3
38. The reagent used for the separation of acetaldehyde from acetophenone is
(1) NaHSO 4 (2) C 6 H 5 NHNH 2 (3) NH 2 OH (4) NaOH I 2
Sol: (1) NaHSO 3 gives the addition reaction with Aldehyde and only aliphatic ketone. Acetophenone is the
aromatic ketone so it does not give the addition product with NaHSO 3 aldehyde from the addition product
with NaHSO 3 which on treatment with acid or base give again aldehyde.
OH
|
RCHO HSO 3 Na R C H R CHO ; C 6 H 5 COCH 3 NaHSO 3 No reaction
H or
| OH
SO 3 Na
39. Which of the following aldehydes is most reactive towards nucleophilic addition reactions
(1) HCHO (2) CH 3 CHO (3) C 2 H 5 CHO (4) CH 3 COCH 3
Sol: (1) Because alkyl group is absent and they have +ve inductive effect and increases the electron
density on the carbonyl group.
40. Which one of the following gives iodoform test
(1) Formaldehyde (2) Ethyl alcohol (3) Benzyl alcohol (4) Benzaldehyde
Sol: (2) The compound having -hydrogen will give iodoform test. Ethyl alcohol and secondary alcohols
also give positive iodoform test because by the action of halogens in alkaline medium, they are oxidesed
to acetaldehyde and methyl ketones respectively.
C H 3 C H 2 O H I
2
C H 3 C H O I
2
C I 3 C H O H2 O
/ NaOH
CH I3
N aO H NaOH
Sol: (4) During reaction Ag gets reduced Ag metal and forms silver mirror.
42. Among the following compounds, which will react with acetone to give a product containing CN
(1) C 6 H 5 NH 2 (2) (CH 3 ) 3 N (3) C 6 H 5 NHC 6 H 5 (4) C 6 H 5 NHNH 2
Sol: (ad) C 6 H 5 NH 2 and C 6 H 5 NH .NH 2 will give the compounds containing C N -group.
43. Which of the following does not give yellow precipitate with I2 and NaOH
(1) C 2 H 5 OH (2) CH 3 CHO (3) CH 3 COCH 3 (4) HCHO
I / NaOH
Sol: (4) 2
HCHO
No reaction
O O
|| ||
Lewis acid
47. ArH R C Cl
Ar C R HCl is an example of
(1) Friedel-Craft's alkylation (2) Friedel-Craft's acylation
(3) Cannizzaro reaction (4) Claisen condensation
anhyd. AlCl 3
Sol: (2) ArH R CO Cl Ar CO R HCl This reaction is Friedel–Craft’s acylation.
48. Which of the following fails to answer the iodoform test.
(1) Pentanone–1 (2) Pentanone–2 (3) Propanone–2 (4) Ethanol
O
||
Sol: (1) 1-pentanone is an impossible compound does not have CH 3 C group.
CARBOXYLIC ACIDS
49. Which of the following is the weakest acid
(a) Phenol (b) CH 3 COOH (c) HCOOH (d) Benzoic acid
S0l: (a) Phenol is a weaker acid than carboxylic acids.
50. Pyruvic acid is obtained by
(a) Oxidation of acetaldehyde cyanohydrin (b) Oxidation of acetone cyanohydrin
(c) Oxidation of formaldehyde cyanohydrin (d) All of these
CN
|
H2O [O ]
Sol: (a) CH 3 C H HCN CH 3 C H CH 3 CH COOH CH 3 C COOH
|| | | ||
O OH OH O
Pyruvic acid
51. The product obtained by dry distillation of calcium formate on reacting with ammonia yields
(a) Formamide (b) Acetamide
(c) Acetaldehyde ammonia (d) Urotropine
Sol: (d) 2(HCOO )2 Ca 2 HCHO 2 CaCO 3
Dry distillati on
6 HCHO 4 NH 3 (CH 2 )6 N 4 6 H 2 O
Urotropin
NH 3
52. In the reaction C 8 H 6 O 4 X Y The compound X is
(a) Phthalic anhydride (b) Phthalic acid (c) o-xylene (d) Benzoic acid
O
||
C CONH2
COOH
O +NH3
Sol: (a) COOH C COOH
||
53. Ethyl acetate reacts with CHO3 MgBr to form
(a) Secondary alcohol (b) Tertiary alcohol
(c) Primary alcohol and formic acid (d) formicAcid
O O MgBr OH O
|| | | ||
Sol: (b) CH 3 C O C 2 H 5 CH 3 MgBr CH 3 C O C 2 H 5 C H 3 C OH
H 2O H 2O
C H 3 C C H 3
Ethyl acetate | Br |
CH 3 Mg
OH CH 3
CH 3 CH 3
| |
Excess of H2O
CH 3 C OMgBr CH 3 C OH
CH 3 MgBr | |
CH 3 CH 3
t - Butanol
56. 0.2 gm of fine animal charcoal is mixed with half litre of acetic acid (SM ) solution and shaken for 30
minutes
(a) The concentration of the solution decreases (b) Concentration increases
(c) Concentration remains same (d) None of these
Sol: (a) Activated charcoal adsorbed the impurity of acetic acid by which the concentration of acetic acid
solution decrease.
57. Dimerisation in carboxylic acid is due to
(a) Ionic bond (b) Covalent bond
(c) Coordinate bond (d) Intermolcular hydrogen bond
Sol: (d) Intermolecular hydrogen bonding leads to dimerisation of carboxylic acid in non-aqueous
solvents.
58. A colourless organic compound gives brisk effervescences with a mixture of sodium nitrite and dil. HCl. It
could be
(a) Glucose (b) Oxalic acid (c) Urea (d) Benzoic acid
Sol: (c) NaNO2 HCl HNO 2 NaCl
H 2 NCONH 2 HNO 2 CO 2 NH 3 H 2 O N 2 CO 2 evolve with brisk effervescence.
Urea
59. What is formed when benzoyl chloride reacts with aniline in presence of sodium hydroxide
(a) Acetanilide (b) Benzanilide (c) Benzoic acid (d) Azobenzene
NaOH
Sol: (b) It is known as Schotten Baumann reaction. C6 H 5 NH 2 ClCOC6 H 5 C 6 H 5 NHCOC 6 H 5 HCl
Aniline Benzoyl chloride Benzanilide
Sol: (a) Due to –I effect of three F atom CF3 COOH is a strong acid.
61. Aspirin is obtained by the reaction of salicylic acid with
(a) Acetone (b) Acetaldehyde (c) Acetyl chloride (d) Acetic anhydride
OH OCOCH3
COOH COOH
+ (CH3CO)2O + CH3COOH
Acetic anhydride
Salicylic acid Aspirin or Acetyl
salicylic acid
Sol: (d)
62. Oxalic acid when reduced with zinc and H 2SO 4 gives
(a) Glyoxallic acid (b) Glyoxal (c) Glycollic acid (d) Glycol
COOH CH 2 OH
Sol: (c) |
COOH
Zn
4 [ H ]
|
H 2O
H 2 SO 4 COOH
Oxalic acid Glycolic acid