10.aldehyde - Ketone PDF

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Summary
Mechanism:
Nucleophile (Nu") attacks the carbonyl group perpendicular to the plane of sp2 hybridised orbitals
of
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carbonyl carbon.
ln the process, hybridisation of carbon changes from sp2 to sp3.
e.
A tetrahedral alkoxide is formed as intermediate.
Reactivity: Aldehydes are more reactive than ketones in nucleophilic addition reactions
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There are two factors which influence the reactivity of ketone and aldehyde.
(i) Inductive effect (ii) Steric factor
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(i) + l effect of alkyl group decreases the amount of charge on C+ (C+ - O-). in ketones.
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(ii) Steric effect also causes the less reactivity of carbonyl group.
Addition elimination reactions:
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certain compounds related to ammonia add to the carbonyl group to form derivatives that are
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important
chiefly for the characterization and identification of aldehydes and Ketones, the product contains
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a carbon nitrogen double bond resulting from elimination of a molecule of water from the initial
addition products.
..
Reaction with ammonia derivatives ( H 2 N − Z ) :
This reaction is nucleophilic addition followed by water elimination.
Beckmann Rearrangement in Oxime:
Aldol Condensation:
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It is condensation between two moles of carbonyl compounds among which at lease one must have
α – hydrogen atom in dilute basic media to get α, β – unsaturated aldehyde / ketone via the
formation of β – hydroxy aldehyde / ketone.
Cannizzaro reaction:
Carbonyl compounds not having α – hydrogen atom undergo disproportionation or redox reaction
in strong basic media.
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Perkin reaction:
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when aromatic aldehyde like benzaldehyde is treated with anhydride in the presence of sodium
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salt of acid from which anhydride is derived, we get α, β -unsaturated acid
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Baeyer – Villiger Oxidation:

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It is preparation of ester from ketone using peracid.

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If migratory aptitude of R’ is greater than R.

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Haloform reaction:
Acetaldehyde and methylalkyl ketones react rapidly with halogen (Cl2, Br2, or I2) in the presence
of alkali to give haloform and acid salt.

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Practice Questions
1. The correct sequence of reagents for the following conversion will be (2017)
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2.
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3. Which compound would give 5-keto-2-methyl hexanal upon ozonolysis? (2015)

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4. The major product in the following reaction is (2014)
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5. The most suitable reagent for the conversion of R —OH to R —CHO is (2014)

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6. The major product H in the given reaction sequence is
(2012)
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e.
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7. The number of aldol reaction(s) that occurs in the given transformation is (2012)
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8. Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E.
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Compound E on further treatment with aqueous KOH yields compound F. Compound F is (2007)
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9. The smallest ketone and its next homologue are reacted with NH2OH to form oxime. Which one is
correct statement regarding the same? (2006)

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10. Butan-2-one can be converted to propanoic acid by which of the following reagent?
(2006)
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11.
e.
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12. The order of reactivity of phenyl magnesium bromide with the following compounds is
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(2004)
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13. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives
(2001)

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14. The appropriate reagent for the following transformation:
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15. Which of the following has the most acidic hydrogen? (2000)
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16. The enol form of acetone, after treatment with D2O, gives (1999)
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17. Which of the following will react with water? (1998)
18. Which of the following compounds is oxidised to prepare methyl ethyl ketone? (1987)

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19. The compound that will not give iodoform on treatment with alkali and iodine is (1985)
20. The Cannizzaro’s reaction is not given by (1983)
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21. When acetaldehyde is treated with Fehling's solution, it gives a precipitate of (1981)
e.
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22. A compound that gives a positive iodoform test is (1982)
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23. The reagent with which both acetaldehyde and acetone react easily is (1981)
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24. Reagent(s) which can be used to bring about the following transformation is (are) (2016)

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25. The major product of the following reaction is (2015)
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26. After completion of the reactions (I and II), the organic compound (s) in the reaction mixtures is/are
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(2013)
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27.
t
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e.
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28.
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29.
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t
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30.
e.
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31.
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t
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32. The reagents used to convert
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33. Of the following, which compound is an acetal?

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34. The major product of the reaction is:

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t
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e.
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35. Which of the following reagents can be used for the given reaction?
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36. Give the decreasing order of the following compounds in the extent of hydration or towards NA
(nucleophilic addition) reaction.

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a. IV > III > II > I
b. I > II > III > IV
c. IV > II > III > I
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d. I > III > II > IV
e.
37. Give decreasing order of the following compounds towards NA (nucleophilic addition) reaction.
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a. I > II > III > IV

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b. IV > III > II > I
c. II > III > IV > I
d. I > IV > III > II
38.

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39. When CH3CHO is reacted in the presence of a base with excess of HCHO, which statement is true?
a. Only aldol-type (Claisen—Schmidt) reaction takes place.
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b. Only Cannizzaro-type (crossed Cannizzaro) takes place.
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c. First aldol-type and then Cannizzaro type reaction take place.
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d. First Cannizzaro-type and then aldol-type reaction take place.
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40. How will you distinguish the products obtained by acidic hydrolysis of I and II ?
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41. Give the decreasing order of hydrate formation of the following:

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I. HCHO
II. PhCHO
III. Chloral
IV. Acetone
a. III > I > II > IV
b. IV > II > I > III
c. I > III > II > IV

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d. IV > II > III > I
42.
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a. I, III
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b. I, IV
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c. II, III
d. II, IV
43.
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a. I, IV
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b. I, III
e.
c. II, III
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d. II, IV at
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44. Which oxime on acetylation followed by reaction with Na2CO3 would give propane nitrile?
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45.

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t
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e.
46.
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47.
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48.
t
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e.
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49.
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50.
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t
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51. Two moles of HCHO and 1 mol of PhCHO react with conc. NaOH. What are the products
e.
quantitatively?
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a. 1 mol of PhCH2OH, 2 mol of CH3OH, and 1 mol of HCOONa.
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b. 1 mol of PhCH2OH, 1.5 mol of CH3OH, and 0.5 mol of HCOONa.
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c. 1 mol of PhCH2OH, 0.5 mol of CH3OH, and 1.5 mol of HCOONa.
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d. 1.5 mol of PhCH2OH, 1 mol of CH3OH, and 1 mol of HCOONa.

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52. One mole of HCHO and 2 mol of PhCHO react with conc. NaOH. What are the products
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quantitatively?
a. 1 mol of HCOONa, 1 mol of PhCH2OH, and 1 mol of PhCOONa.

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b. 1 mol of HCOONa, 1 mol of PhCH2OH, and 0.5 mol of PhCOONa.

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c. 1 mol of HCOONa, 1.5 mol of PhCH2OH, and 0.5 mol of PhCOONa.
d. I mol of HCOONa, 2 mol of PhCH2OH, and 2 mol of PhCOONa.
53. Identify the following disproportionation reaction

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t
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54. Aldehydes with α-H atom do not undergo disproportionation reaction because:
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a. Bond energy of (C—H) bond is increased due to (—CHO) group.
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b. Aldehyde is enolised in basic condition. at
c. Both
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d. None
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55. In Cannizzaro reaction, which of the following is a better hydride donor?

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a. (A)
b. (B)
c. Both
d. None
56.

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Select the correct statement:
a. Oxidation number of C in RCHO increases and that of R’CHO decreases.
b. Oxidation number of C in RCHO decreases and that of R’CHO increases.
c. Oxidation number of C remains unchanged in both but that of oxygen is affected.
d. In CH3CHO and C6H5CHO, the former can act as RCHO (hydride donor).
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57. compound (A) given below can undergo Cannizzaro reaction itself and crossed Cannizzaro reaction
with HCHO. It is because of:
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a. It has three ( - CH2OH) groups.

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b. It has an aldehyde group.

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c. It has non-enolisable α-H atom.
d. It has a keto group.

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58.
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Which of the following sequence of reagents is correct in the conversion of (A) to (B)?

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59. Which method is feasible for the preparation of compound (X) only?
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e.
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60.
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t
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e.
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61. The final product (E) in the following reaction is:
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62. Which of the following is not the mechanism of Cannizzaro reaction?

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63. Which of the following is not the mechanism of Cannizzaro reaction when the concentration of base
is very high?
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64. Clemmensen’s reduction will convert cyclohexanone into:
65.
In this sequence of reaction, the (Z) is:

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a. Ethylene bromide
b. Ethanol
c. Ethyl bromide
d. Ethylidene bromide
66. Ethylidene chloride is hydrolysed with aqueous NaOH. The product formed is:
a. Ethanol
b. Ethanal
c. Ethanone
t
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d. Ethane
e.
67. The vapours of ethyl alcohol are passed over red hot copper at 573K to form:
a. Methane
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b. Formaldehyde
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c. Acetone
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d. Acetaldehyde
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68.
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In the above sequence of reaction, (Y) is:
a. Isobutyl alcohol
b. n-Butyl alcohol
c. Tertiary butyl alcohol
d. Isobutylene
69.The chemical reaction of acetaldehyde and ammonia results in:
a. Ethylamine

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b. Hexamethylene tetra amine
c. Acetic acid
d. Acetaldehyde ammonia
70. Which of the following ketone will not give yellow precipitate with NaOH/I2?
a. 2-Pentanone
b. Benzophenone
c. Acetone
d. 2-Hexanone
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71. Which is the Wacker process?
e.
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72. 2-Propanone (acetone) can be obtained by Wacker's process starting with:

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a. Propyne
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b. Propan-2-ol
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c. Propene
d. Propanol- 1 -ol
73. When di-ethyl cadmium [(C2H5)2Cd] is treated with acetyl chloride [CH3COCl], the main product is
likely to be:
a. Acetone
b. Ethyl methyl ketone
c. Diethyl ketone
d. Acetaldehyde

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74.
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e.
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76.
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77.
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78. Name the following reaction.
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e.
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79. A compound has molecular formula C6H12O. It does not reduce Tollens or Fehling's reagent, but gives
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a crystalline derivative with 2,4-dinitro-phenyl hydrazine. With alkali and I2, it gives yellow solid with a
medicinal odour. Clemmensen reduction converts it to 2-methylpentane. The structural formula of the
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compound is most likely to be:

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80. A substance (C5H10O) does not reduce Fehling's solution, forms a phenylhydrazone, shows the
haloform reaction, and can be converted into n-pentane by strong reduction. The structural formula of
the original substance is:
81. Benedict's solution and Fehling's solution are similar in all of the following except:

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82. On treatment of acetone with dilute Ba(OH)2, the product formed is:
a. Aldol
b. Phorone
c. Propionaldehyde
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d. 4-Hydroxy-2-pentanone
e.
83. Formalin is:
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84. Which of the following is paraldehyde?

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85. The product formed by the reaction of acetaldehyde with excess of ethanol in the presence of
sulphuric acid is:
86. Which of the following will not be formed when calcium formate is distilled with calcium acetate?
a. Acetone
b. Propanal
c. Ethanal

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d. Methanal
87. Cyclohexanone is subjected to reduction by NaBH4. The product formed is:
a. Cyclohexane
b. Cyclohexanal
c. Cyclohexadiene
d. Cyclohexanol
88.
t
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e.
In the above sequence (X) can be:
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a. H2/Ni at
b. NaBH4
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c. K2Cr207/H+
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d. Both (a) and (b)

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89. When acetaldehyde is treated with hydroxylamine, the medium should be:
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a. Highly basic
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b. Highly acidic
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c. Moderately acidic
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d. None of the above
90. In order to prepare acetone from acetyl chloride in one step, which of the following reagents will be
best?
a. Reduction with H2/Pd-BaSO4
b. Reduction with HI
c. Grignard's reagent
d. Dimethyl cadmium

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91. Which of the following will not reduce Fehling’s solution?
a. Formic acid
b. Ethanal
c. 2-Methyl propanal
d. All will reduce
92. Which of the following reagents can help in separating mixture of acetone and CCl4?
a. NaOH
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b. NaCI
c. NaHSO3
e.
d. None of the above
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93.
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a. 4
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b. 3
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c. 2
d. 5
94.
a. 3

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b. 4
c. 6
d. 9
95.
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a. 2
e.
b. 3
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c. 4 at
d. 5
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96.
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a. 3
b. 2
c. 1
d. 4
97. No. of isomer of carbonyl compound of formula C5H10O give positive iodoform test (including
stereoisomers)?
a. 3

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b. 2
c. 1
d. 4
98. How many compounds give positive Tollens test?
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a. 4
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b. 5
c. 6
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d. 3
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99. How many isomer of compound C4H10O give positive Iodoform test? (Excluding stereoisomers)
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a. 1
b. 3
c. 2
d.4
100. How many isomers of C4H10O give positive iodoform test? (Including stereoisomers)
a. 3
b. 4

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c. 2
d. 1
101. Assertion (A): The following intramolecular aldol reaction occurs.
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Reason (R): The carbanion does not add to C – 4 because a strained four – membered ring would result.
a. If both (A) and (R) are true and (R) is the correct explanation of (A).
e.
b. If both (A) and (R) are true but (R) is not the correct explanation of (A).
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c. If (A) it true but (R) is false.
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d. If (A) is false but (R) is true.
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102. Assertion (A): The equilibrium constant for cyanohydrin formation is ∪ 1013 times greater for
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cyclohexane than for cyclopentanone.

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Reason (R): For a five-membered ring, reactions are more favourable when a ring C changes from sp3 to
sp2 because eclipsing interactions are removed.
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d. If (A) is false but (R) is true.
103. Assertion (A): The following reaction occurs.

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Reason (R): Undergoes disproportionation reaction since the mobility of α-H atom is arrested by the
steric effect of the two bulky methyl groups.
d. If (A) is false but (R) is true
104. Assertion (A): Pentan-3-one on reaction with NaHSO3 gives sodium bisulphite adduct product.
Reason (R): (C = O) group of pentan-3-one is sterically hindered and nucleophile SO32- is also of large size,
so nucleophilic addition reaction does not occur.
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c. If (A) it true but (R) is false. at
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105. Assertion (A): The following reaction occurs.

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Reason (R): The semicarbazone of (A) (pentan-2-one) exists in two geometrical isomers.
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106. Assertion (A): The following cross Cannizzaro reaction occurs.

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Reason (R): Rate of reaction is:
Rate = K[Aldehyde (I)] [Aldehyde (II)] and bimolecular.
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107. Assertion (A): The following intramolecular aldol reaction occurs.
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Reason (R): (CHO) is a better acceptor than (C=O).

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108. Assertion (A): The reaction of 1 mol each of (MeCH = O) with glycerol
gives six separable isomers.

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Reason (R): Acetaldehydes react with I - and 2-OH group of glycerol to form five-membered cyclic acetal.
In the ring closure, two chiral centres are formed and thus we have two pairs of enantiomers: cis and
trans.
When acetaldehydes react with 1- and 3-OH groups, a six-membered cyclic acetal is formed giving two
diastereomeric products (cis and trans). These diastereomers are achiral.
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109. Fehling’s solution A consists of an aqueous solution of copper sulphate, while Fehling’s solution B
consists of an alkaline solution_____. (1990)
e.
a. sodium tartarate
b. potassium tartarate
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c. sodium potassium tartarate
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d. None of the above.
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110. Carbonyl compounds undergo nucleophillic addition because of
(a) more stable anion with negative charge on oxygen and less stable carbocation
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(b) electromeric effect

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(c) electronegativity difference of carbon and oxygen atoms

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(d) none of these

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111. If formaldehyde and KOH are heated, then we get
(a) methyl alcohol
(b) acetylene
(c) methane
(d) ethyl formate
112. Which of the following will not give iodoform test?

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(a) ethanol
(b) ethanal
(c) pentan-3-one
(d) pentan-2-one
113. Oxidation of toluene to benzaldehyde by the use of chromyl chloride is called
(a) Wurtz reaction
(b) Fittig reaction
(c) Etard's reaction
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(d) Rosenmund's reaction
e.
114. Which aldehyde will give Cannizzaro’s reaction?
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115. Formaldehyde when reacted with methyl magnesium bromide followed by hydrolysis gives:
(a) HCHO
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(b) CH3COOH
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(c) C2H5OH
(d) CH3CHO
116. Ketones (R1COR2); R1 =R2 = alkyl group, can be obtained in one step by
(a) hydrolysis of esters
(b) oxidation of primary alcohols
(c) oxidation of secondary alcohols
(d) reaction of acid halides and alcohols

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117. The product formed by the reaction of chlorine with benzaldehyde in the absence of catalyst is (a)
benzoyl chloride
(b) benzyl chloride
(c) chlorobenzene
(d) o-chlorobenzaldehyde
118. When aliphatic aldehyde is heated with Fehling solution, the product formed is
(a) CuO
(b) Cu2O
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(c) CuSO4
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(d) Cu
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119. Which of the following reacts with both acetaldehyde and acetone?
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(a) Fehling's solution
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(b) CH3MgBr
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(c) Tollen's reagent

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(d) Benedict solution

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120. The reagent used for the separation of acetaldehyde from acetophenone is
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(a) NH2OH
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(b) NaHSO3
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(c) NaOH/I2
(d) C6H5NHNH2

@aakashallen
Answer Key:
1. a 2. a 3. b 4. d 5. d 6. a 7. c 8. a 9. b 10. c
11. c 12. c 13. a 14. b 15. b 16. b 17. b 18. c 19. c 20. b
21. c 22. c 23. c 24. c 25. a 26. c 27. c 28. c 29. b 30. b
31. a 32. b 33. b 34. d 35. c 36. a 37. c 38. c 39. c 40. a
41. a 42. b 43. a 44. a 45. c 46. b 47. a 48. a 49. c 50. a
51. c 52. c 53. d 54. b 55. b 56. a 57. c 58. b 59. a 60. c
61. d 62. d 63. d 64. b 65. c 66. b 67. d 68. c 69. d 70. b
71. d 72. c 73. b 74. a 75. c 76. b 77. a 78. d 79. a 80. a
81. d 82. d 83. b 84. b 85. c 86. b 87. d 88. b 89. c 90. d
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91. d 92. c 93. b 94. a 95. a 96. b 97. b 98. a 99. a 100. c
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101. d 102. a 103. a 104. d 105. d 106. d 107. d 108. a 109. c 110. a
111. a 112. c 113. c 114. c 115. c 116. c 117. a 118. b 119. b 120. b
e.
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“Detail solutions are mentioned in the content library”
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@aakashallen

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Beckmann Rearrangement in Oxime:

Baeyer – Villiger Oxidation:

It is preparation of ester from ketone using peracid.

If migratory aptitude of R’ is greater than R.

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3. Which compound would give 5-keto-2-methyl hexanal upon ozonolysis? (2015)

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4. The major product in the following reaction is (2014)

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6. The major product H in the given reaction sequence is

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14. The appropriate reagent for the following transformation:

17. Which of the following will react with water? (1998)

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20. The Cannizzaro’s reaction is not given by (1983)

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25. The major product of the following reaction is (2015)

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33. Of the following, which compound is an acetal?

34. The major product of the reaction is:

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a. IV > III > II > I

b. I > II > III > IV

c. IV > II > III > I

a. I > II > III > IV

b. IV > III > II > I

c. II > III > IV > I

d. I > IV > III > II

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a. Only aldol-type (Claisen—Schmidt) reaction takes place.

41. Give the decreasing order of hydrate formation of the following:

a. III > I > II > IV

b. IV > II > I > III

c. I > III > II > IV

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d. IV > II > III > I

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d. 1.5 mol of PhCH2OH, 1 mol of CH3OH, and 1 mol of HCOONa.

a. 1 mol of HCOONa, 1 mol of PhCH2OH, and 1 mol of PhCOONa.

b. 1 mol of HCOONa, 1 mol of PhCH2OH, and 0.5 mol of PhCOONa.

c. 1 mol of HCOONa, 1.5 mol of PhCH2OH, and 0.5 mol of PhCOONa.

d. I mol of HCOONa, 2 mol of PhCH2OH, and 2 mol of PhCOONa.

53. Identify the following disproportionation reaction

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55. In Cannizzaro reaction, which of the following is a better hydride donor?

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Select the correct statement:

a. Oxidation number of C in RCHO increases and that of R’CHO decreases.

b. Oxidation number of C in RCHO decreases and that of R’CHO increases.

c. Oxidation number of C remains unchanged in both but that of oxygen is affected.

a. It has three ( - CH2OH) groups.

b. It has an aldehyde group.

c. It has non-enolisable α-H atom.

d. It has a keto group.

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62. Which of the following is not the mechanism of Cannizzaro reaction?

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64. Clemmensen’s reduction will convert cyclohexanone into:

In this sequence of reaction, the (Z) is: