® Aldol & Similar Name Reactions
ALDOL & SIMILAR NAME REACTIONS
(1) CANNIZARO REACTION
This reaction is given by aldehyde having no - hydrogen in the presence of conc.
NaOH/ or KOH/ .
O O
H – C – H KOH H – C – O K + CH3OH
+
Mechanism :
O O O O O
HO r.d.s.
H–C–H H–C–H C CH3–O + H–C–O–H CH3OH + H–C–O
OH H H
In the presence of a very strong concentration of alkali, aldehyde first forms a doubly charged
anion (I) from which a hydride anion is transferred to the second molecule of the aldehyde to form
acid and an alkoxide ion. Subsequently, the alkoxide ion acquires a proton from the solvent.
O O O
OH
H – C – H OH H–C–H H–C–H
(I)
OH O
O H O H
H–C–H + C=O H – C + H–C – O
(I)
O H O H
H2O
HCH2O HCH2OH + OH
From solvent
1. Which of following will not undergo Cannizaro reaction
CHO
CHO
(A) (B) (C) (D) Cl3C–CHO
O CHO Cl
AR0001
O
H2 HCHO
2. Ph – C – Cl Pd –BaSO Ph – CHO (C) + (D)
4
Product (C) & (D) are :
(A) Ph–CO2H, Ph–OH (B) Ph–CO2–,HCO2–
(C) Ph–CH2OH, H–CO2– (D) Ph–CO2–,CH3OH
AR0002
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CHO conc.NaOH H
+
3. (A) (B)
CHO
Product (B) is :
O O
O C
CH2–O–C
(A) H2C=CH–CO2H (B) CH 2 CH2 (C) (D)H2C=C=O
C O CH2–O–C
O O
AR0003
4. (i) HCHO NaOD (ii) DCHO NaOD
AR0004
18
5. (i) Ph–CHO OD / DOD (ii) Ph–CHO OH
AR0005
KOH KOH
6. (i) Ph – CHO + HCHO (ii) Ph – C – C – H
O O
AR0006
7. (i) MeCH2 – CHO KOH (ii) Me2CH – CHO conc.KOH
AR0007
8. (i) Me–NO2 + HCHO KOH (ii) MeCHO – HCHO KOH
(excess) (excess)
AR0008
– – +
Aq.OH
A Conc. OH H
9. PhCOCHBr2 B C ; the compound ‘C’ is :
(A) PhCH(OH)CHO (B) PhCH(OH)COOH
(C) PhCOOH (D) None of these
AR0009
10. Match the column :
Column - I Column - II
(A) HCHO + NaOD (conc.) (P) DCOO– + CDH2OH
(B) DCHO + NaOH (conc.) (Q) DCOO– + CD3OH
(C) DCDO + NaOH (conc.) (R) DCOO– + CDH2OD
(D) DCHO + NaOD (conc.) (S) HCOO– + CH3OD
AR0010
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® Aldol & Similar Name Reactions
O O
NaOH KMnO4
11. C—C—H (conc.) A B NaOH/CaO C ; Product ‘C’ is :
O
CHO
(A) (B) (C) (D)
AR0011
O
C CH
1% HgSO 4 / Dil.H 2 SO 4 I 2 / NaOH
12. H
X ; X is :
O O O O
COOH COCH3 CH2CHO
(A) (B) (C) (D)
AR0012
13. The cannizaro reaction of Ph COCHO forms the product(s)
(A) PhCOCH2OH + PhCOCO2– (B) PhCH – CO–2
OH
(C) PhCO2– + PhCOCH2OH (D) Both (A) and (C)
AR0013
O
P2O5 ( i) CH 3MgBr (i) I 2 Ca(OH) 2
14. C – NH2 A (ii)H 3O
B (ii) C ;
(iii) –CHI 3
Product is:
O O
(A) C – NH2 (B) C – OH (C) C (D) C – CH2CH3
O O
AR0014
CHO
conc. KOH
15.
CHO
True about this reaction is / are
(A) Cannizaro name is associated with this reaction
(B) It is a disproportion reaction
(C) It is a bimolecular reaction in r.d.s.
(D) All of these
AR0015
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O3
16. Zn
(A) conc.KOH (B)
(1 mole)
End product (B) of above reaction is :
+
CHO +
CO2– K CH2OH CO2– K
(A) (B) (C) (D) +
CH2OH CH2OH CH2OH CO–2 K
AR0016
17. The major product pair of the following reaction will be :
CHO
HCHO Products
NaOH (aq)
COONa CH2 OH CH2OH COONa
CH3OH
(A) + CH3OH (B) + (D) +
+ HCOONa (C)
HCOONa
AR0017
18. Reactant ‘X’ will be :
CH2OH
– +
+
COO Na
H O3 NaOH
X Y Zn Z1 + Z2 +
–
OH /
Ph – C = CH – C – Ph
CH3 O
OH OH
(A) Ph – CH – CH – Ph (B) Ph – CH – CH – CH3
CH3 Ph
CH3 OH OH
(C) Ph – CH – C – Ph (D) Ph – CH2 – CH – Ph
CH3
AR0018
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® Aldol & Similar Name Reactions
19. An organic compound neither reacts with neutral ferric chloride solution nor with Fehling solution,
It however, reacts with Grignard reagent and gives positive iodoform test. The compound is -
[JEE-MAIN (APRIL)-2019]
OH
O O
CH3 O
CH3 CH3 C2H5
(1) C2H5 (2) (3) (4)
H CH3
OH O
O O
AR0019
20. Identify A in the following chemical reaction
CHO
(i) HCHO, NaOH
(ii) CH 3 CH 2 Br ,NaH,DMF A [JEE-MAIN-2021]
CH3O (iii) HI,
O
CH2OH
C – OCH2CH3
(1) (2)
CH3O
HO
CH 2I CH2OH
(3) (4)
HO HO
AR0083
21. In the following sequence of reactions, [JEE-MAIN-2021]
H /H 2O KIO
C3H6 A dil KOH B+C
The compounds B and C respectively are :
(1) CI3COOK, HCOOH (2) CI3COOK, CH3I
(3) CH3I, HCOOK (4) CHI3, CH3COOK
AR0084
22. The correct structure of product 'A' formed in the following reaction. [JEE MAINS 2022]
NaOD
O
PhCHO Ph CHO A || (Ph is –C6H5)
in D2 O
Ph C O
OD OH OD OD
(1) H (2) H (3) D (4) D
Ph H Ph H Ph H Ph D
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