REDUCTION OXIDATION (Organic Chemistry)

REDUCTION SUMMARY
Name Reagent Function

Wolf Kishner Reduction (i) N2 H4 / (ii) KOH, Δ

Clemenson Reduction Zn − Hg/HCl

Mozingo Reduction
Dry HCl followed by Raney Ni
Stephen's Reduction SnCl2 /HCl followed by H3 O + R − C ≡ N ⟶ R − CH = O

MPV Reduction

Hydroboration Reduction (i) B2 H6 (ii) AcOH, H2 O

Bouvoult Blank Reduction Na in EtOH R − COO − R → RCH2 OH + ROH

Transfer Hydrogenation N2 H4 /H2 O2

Rosenmund Reduction H2 , Pd − BaSO4

Birch Reduction Na in Liq. NH3

Red phosphorus in presence of HI Red P + HI

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OXIDATION
1.1 Introduction
(i) oxidation is defined as the addition of oxygen (a)
(electronegative) element to a substance or removal
of hydrogen (electropositive) element from a substance.
or
Oxidation of an organic molecule usually corresponds (b)
to increasing its oxygen content or decreasing its
hydrogen content.

(c)

(ii) Oxidation of an organic compound may be more

broadly defined as a reaction that increases its
content of any element more electronegative than (d)
carbon. Replacing hydrogen atoms by chlorine
atoms is an oxidation

When organic compound is oxidised, oxidising agent General Reaction

used is reduced. When an organic compound is
reduced, the reducing agent used must be oxidized.
1.2 Oxidation of Alkanes
Different products are formed by the use of different
oxidising agents or different reaction conditions.
(i) By KMOO or K 2 Cr2 O7 : Alkanes are usually not
4
affected by oxidising agents like KMnO4 or K 2 Cr2 O7 .
However, alkanes having tertiary hydrogen are
oxidised by these oxidising agents to an alcohol. Stereochemistry: anti addition in diol formation.
KMnO4
(CH3 )3 CH → (CH3 )3 COH
(Isobu tan e) (Tertiarybutylalcohol)
Cu/523 K/1000 atm
Ex. (a) 2CH4 + O2 → 2CH3 OH (methanol)
9:1
Mo2 O3 Ex.
(b) CH4 + O2 HCHO + H2 O
Δ
(CH3 COO2 )Mn
(c) 2CH3 − CH3 + 3O2 2CH3 COOH +
Δ
Burn
2H2 O(iv) CH4 + O2 ⟶ C + 2H2 O
limited carbon
black

1.3 Oxidation of alkenes and alkynes Note: The more highly substituted olifinic bond is more
(i) Baeyer reagent [cold dilute 1% alkaline KMnO4 nucleophilic and therefore reacts faster with the
solution] peroxyacid than the less susbstituted double bond.
Alkene ⟶ Vicinal diol; Alkyne ⟶ Diketone;
Aldehyde ⟶ Acid

(ii) Oxidation with peroxyacids

An alkene is converted to an epoxide by a peroxyacid.
[a carboxylic acid that has an extra oxygen atom in
a − O − O − (peroxy) linkage]. Some simple
peroxyacids (sometimes called peracids) are shown (iii) Oxidation with acidic 𝐊𝐌𝐧𝐎𝟒 [𝐊𝐌𝐧𝐎𝟒 /𝐇 + ]:
below: When alkene & alkyne heated with KMnO4 in acidic or
in alkaline medium; following changes takes place.

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KMnO4 /H + As no water is present in the reaction mixture, no

Reactant =CH2 =CHR =CR1 R 2 ≡CH ≡CR aldehyde hydrate is formed which is oxidized to
group group group group group carboxylic acid in presence of Cr(VI)
Product O=CR1 R 2
CO2 RCOOH CO2 RCOOH
group

Ex.
(b) PDC (Pyridinium Dichromate): Since PDC is less acidic
+ than PCC it is often used to oxidize alcohols that
may be sensitive to acids. In methylene chloride
solution, PDC oxidizes primary and secondary
alcohols in roughly the same fashion as PCC, but much
more slowly. Allylic alcohols are oxidized efficiently
to conjugated enals and enones respectively.

(iv) Oxidation with ozone (ozonolysis):

Like permanganate ozone cleaves double bonds to
give Ketones and aldehydes. However, ozonolysis is
milder, and both Ketones and aldehydes can be (c) Collins Reagent: It is the mixture of chromium trioxide
recovered without further oxidation. with pyridine in dichloromethane. It is used to
Reductive Ozonolysis: selectively oxidize primary alcohols to aldehyde, and
O3 /Zn, H2 O will tolerate many other functional groups in the
Reactant =CH2 =CHR =CR1 R 2 ≡CH ≡CR molecule.
group group group group group It can be used as an alternative to Jones reagent and
Product R1 R 2 C −CO PCC in oxidation of secondary alcohols. Moreover,
HCHO RCHO diketone Collins reagent is especially useful for oxidations of
=O − CHO
acid sensitive compounds. Collins reagent can be
Reductive Ozonolysis: prepared and isolated or generated in situ. This
O3 /H2 O2 complex is both difficult and dangerous to prepare,
Reactant =CH2 =CHR =CR1 R 2 ≡ CH ≡ CR as it is very hygroscopic and can in flame during its
group group group group group preparation.
Product R1 R 2 C
CO2 RCOOH CO2 RCOOH
=O
1.4 Oxidation Reaction of Alcohols:
(i) Oxidation of alcohols using 𝐂𝐫(𝐕𝐈) reagents: (d) Jones Reagent: It is chromium oxide, sulfuric acid and
For oxidation of alcohols to corresponding carbonyl acetone. A mixture of potassium or sodium dichromate
compounds, generally Cr(VI) reagents such as and dilute sulfuric acid can also be used.
K 2 Cr2 O7 , Jones reagent, PCC etc. are employed. For the It is a powerful oxidizing reagent and exhibits only
synthesis of aldehydes, the Collins Reaction or use of poor chemoselectivity.
more modern although more expensive chromium It is used for the oxidation of primary and secondary
(VI) reagents such as PCC and PDC can be an alcohols to carboxylic acids and ketones, respectively,
appropriate choice. Oxidation of alcohols to carbonyl that do not contain acid sensitive group.
compound occurs via Cr(VI) acid monoester. Chromic acid and alcohol then through chromate
Oxidation of fused aromatic system is generally ester gives carbonyl compound in presence of base
carried out using CrO3 reagent (water in this case).
Aldehydes can form hydrates in presence of water and
(a) PCC (Pyridinium Chloro Chromate)
further oxidized to carboxylic acid in presence of
It is other efficient reagent used widely for oxidation
Cr(VI) reagents. Tertiary alcohols cannot be oxidized
of primary and secondary alcohols. Reagent can be
by this reagent.
used in close to stoichiometric amounts with
substrate. PCC is slightly acidic but can be buffered
with NaOAc.

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(ii) Oxidation using Mn reagents

(a) MnO2 : It is used widely as oxidant in organic synthesis. It oxidizes allylic alcohols, acetylenicalcohols and benzylic alcohols
to corresponding aldehydes or ketones. The configuration of double bond is preserved in the reaction.
(b) KMnO4 : Manganese can function as oxidant when it is in +7 oxidation state. KMnO4 is one such oxidant. It is a very strong
oxidizing agent.
Alkyl side chainson aromatic rings are oxidized to carboxylic acid group. This method is more generally applied to methyl
group, however, longer side chains can also be cleaved. Tertiary alkyl groups are not oxidized and are usually accompanied
by ring cleavage. KMnO4 is also used to oxidize primary alcohol andaldehyde to corresponding carboxylic acid.
Ex. Write the product of following reaction when X istreated with
(i) Jones reagent (ii) PCC
(iii) Oppenauer oxidation (iv) MnO2 (v) KMnO4
CH3 − CH = CH − CH − CH2 − CH2 − OH
OH
(X)
(c) Oppenaur's oxidation
(i) This reaction involves the oxidation of a secondary alcohol with a ketone and base to the corresponding ketone.
(ii) Commonly used bases are aluminium tert-butoxide.

(d) Kornblum oxidation [(i) DMSO (ii) NaHCO3 ]

DMSO DMSO DMSO
(i) RCH2 X → RCHO; (ii) R 2 CH − X → R 2 CO; (iii) R 3 C − X → No oxidation
NaHCO3 NaHCO3 NaHCO3

1.5 Oxidation reaction of Carbonyl Compound

(i) Popoff's rule (Acidic 𝐊𝐌𝐧𝐎𝟒 & 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕 as oxidising agent):
(a) Aldehydes are oxidised to carboxylic acid having same number of C atoms as aldehyde.
HCHO + [O] ⟶ HCOOH; RCHO + [O] ⟶ RCOOH
(b) Ketones are oxidised with difficulty.
They are oxidised only on heating with a strong oxidising agent.

(c) In case of mixed or unsymmetrical ketones the > C = O group remains with the smaller alkyl group.
[O] [O]
CH3 COCH2 CH3 ⟶ 2CH3 COOH; CH3 COCH2 CH2 CH3 ⟶
CH3 COOH3 CH3 CH2 COOH
Remarks: Primary alcohol forms a chromate ester with chromic acid.
The chromate ester decomposes in 2nd slow step with the elimination of 𝛼-hydrogen. So the first oxidation product, an
aldehyde is obtained.
In aqueous medium, aldehyde forms a gemdiol (hydrated aldehyde). It is further oxidised to an acid by similar mechanism.
(ii) TOLLEN'S REAGENT:
RCHO (aldehydes) can be easily oxidised to RCOOH (except HCHO that can be oxidised to CO2 ) by weak oxidising agents
like ammonical AgNO3 (Tollen's reagent) hence they are better reducing agents.
Aldehydes reduce Tollen's reagent to Ag and appears in the form of silver mirror is called silver-mirror test. It is given by
all aldehydes and reducing sugars.
Δ
RCHO + 2[Ag(NH3 )+ − −
2 ] + 3OH ⟶ RCOO + 2Ag ↓ +4NH3 + 2H2 O

(iii) FEHLING SOLUTION:

Aldehydes (except benzaldehyde) reduce Fehling's solution (Cu2+ reduced to Cu+ )which is an alkaline solution of
cupric (Cu2+ ) ion complexed with tartrate ion.
Δ
RCHO + 2Cu2+ + 5OH − ⟶ RCOO− + Cu2 O ↓+ 3H2 O
redppt.

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(iv) BENEDICT'S SOLUTION:

Aldehydes also reduce Benedict's solution (Cu2+ complexed with citrate ion) to Cu+ Sodium citrate +NaOH + NaHCO3 +
CuSO4

(v) 𝐇𝐠𝐂𝐥𝟐 and 𝐇𝐠 𝟐 𝐂𝐥𝟐

(i) RCHO + HgCl2 + H2 O ⟶ RCOOH + 2HCl + Hg 2 Cl2
Δ
(ii) RCHO + Hg 2 Cl2 + H2 O → RCOOH + 2HCl + 2Hg ↓ grey ppt.
(vi) SCHIFF'S REAGENT:
Schiff's Reagent is aq. solution of following base decolourised by passing SO2 . Aldehyde restore pink colour of Schiff's
reagent.

Note: Ketons are not easy to oxidize so they do not give these 5 tests. These five tests can be used to distinguish aldehyde and
ketones. Both gives 2, 4 DNP test.
(vii) Oxidation by using 𝐒𝐞𝐎𝟐 :
−SeO2 is a selective oxidizing agent with converts −CH2 − group agjacent to carbonyl group into carbonyl group. The
reagent, in general, oxidises active methylene and methyl groups to ketonic and aldehydic groups respectively.

− Double bonds, triple bonds and aromatic rings may also activate the methylene group. The methylene or methyl group
𝛼 to the most highly substitued end of the double bond is hydroxylated according to the order of preference of oxidation
CH2 > CH3 > CH groups.

− Rate of reactivity order: 2∘ C − H > 1∘ C − H > 3∘ C − H

(viii) BAEYER-VILLIGER OXIDATION:

It is the oxidative cleavage of a carbon-carbon bond adjace to a carbonyl which converts ketones to esters and cyclic
ketones to lactones.
It can be carried out with peracids such as m-CPBA, or with hydrogen peroxide and a lewis acid.

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KETONES ARE DIFFICULT TO OXIDIZE: Ketones can be oxidized from their enolic form at high temperature with very
strong oxidizing agent. Oxidation of ketones is sometimes governed by Popoff's rule. According to this rule carbonyl group
remains with the smaller alkyl group. More electron rich alkene will be easy to oxidized.

(ix) DIOLS OXIDATION BY 𝐇𝐈𝐎𝟒 : (Oxidation by lead acetate is similar to HIO4 oxidation)
Mechanism:

Remarks:
• HIO4 (periodic acid) oxidises vicinal diols (1, 2-diols).
• It brings about oxidative cleavage of vicinal diol.
• It can also oxidise 𝛼-hydroxy carbonyl compound, 𝛼-dicarbonyl compound and 𝛼 hydroxy Imine.
• HIO4 forms a cyclic periodate ester as an intermediate.
General reaction

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EXERCISE – I 7. Bayer's reagent is:

1. Tollen's reagent is (A) alkaline permanganate solution
(A) Cu2 O (B) [Cu(OH)4 ]2− (B) acidified permanganate solution
(C) AgOH (D) [Ag(NH3 )2 ]+ (C) neutral permanganate solution
(D) aqueous bromine solution
2. Major product of following reaction is:
8. An alkyne C7 H12 when reacted with alkaline KMnO4
followed by acidification by HCl, yielded a mixture of
& CH3 CH2 COOH. The alkyne is–

(A) 3-hexyne (B) 2-methyl-2-hexyne

(C) 2-methyl-3-hexyne (D) 3-methyl-2-hexyne
(A) (B)
9. R1 and R 2 in following reaction respectively is:

(C) (D)
(A) Cold alkaline KMnO4 , OsO4 /H2 O2
(B) Cold alkaline KMnO4 , HCO3 H&H3 O+
3. Baeyer's reagent decolourises when reacts with: (C) Cold alkaline KMnO4 , C6 H5 CO3 H
(A) Alkane (B) Alkene only (D) C6 H5 CO3 H, HCO3 H
(C) Alkene and alkyne both (D) Alkyne only
10. Which of the following is/are hydrocarbon?
4. The end products of the reaction are:

(A) P (B) Q
(C) R (D) S
(A)
11. Glucose as well as fructose are oxidized by periodic
acid. The number of moles of HCOOH formed from
(B)
each mole of glucose and fructose are
(A) 5 and 5 (B) 5 and 4
(C) (C) 5 and 3 (D) 4 and 312
(D) Propane
12. Major products of the given reaction will be:
5. X and Y in following reaction is:
KMnO4 / 
1 − Butyne ⎯⎯⎯⎯ →X + Y
(A) CH3 CH2 CH2 COOH + O2
(B) CH3 CH2 COOH
(C) CH3 CH2 COOH + CO2
(D) CH3 CH2 COCH3 + HCOOH (A) (B)

6. Major product of following reaction is/are:

(C) (D) Both (B) and (C)

13. Fehlings solution is

(A) (B)
(A) AgNO3 solution +NaOH solution +NH4 OH
(B) Alkaline solution of Cupric ion complexed with
citrate ion
(C) CH3 CH2 OH (D) (C) Copper sulphate + sodium potassium tartarate
+NaOH
(D) Copper sulphate solution

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14. Secondary alcohols on heating with copper at 300∘ C 19. Major product of following reaction is/are:
give
(A) Alkenes (B) Aldehydes
(C) Ketones (D) tert-alcohols
15. The reagent which can react easily with both
acetaldehyde and acetone is:
(A) Tollens reagent (B) Schiffs reagent (A) R − CHO (B) R − CH2 OH
(C) H2 /Ni (D) Fehling's solution (C) CH3 CH2 OH (D) R − COOH
16. Which of the following compounds is resistant to
periodic acid oxidation?
20. Major product is:
(A) (B)

(C) (D) (A) (B)

17. Identify (P) and (Q) respectively in the given reaction:

(C) (D)

21. The product which is not formed in the following

reaction is:
(A)

(B) (A) HCOOH (B)

(C)
(C) (D)

22. The products of acid hydrolysis of P and Q can be

distinguished by:
(D)

18. Which of the following sets of compounds cannot turn

clear orange solution of CrO3 / aq. H2 SO4 to greenish
opaque solution (A) Lucas reagent (B) 2, 4-DNP
(C) Fehling's solution (D) NaHSO3
23. On catalytic reduction with H2 /Pt how many alkenes
will give n-butane?
(A) 1 (B) 2 (C) 3 (D) 4
24. Major products of following reaction will be:

(A) I, IV (B) II, III (A) Racemic mixture (B) Diastereomers

(C) I, II (D) III, IV (C) Meso (D) Constitutional isomers
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25. Alkene X in following reaction is: 30. If the following compound is treated with Pd in excess
of H2 gas, how many stereoisomers of the product will
be obtained?
(A)

(B)
(A) 1 (B) 2
(C) (C) 3 (D) 4
31. Major product of following reaction is:
(D)

26. Which reagent will be used for the given conversion?

(A) (B)

(C) (D) All of these

(A) Na/ Liq. NH3 (B) H2 , Pd − CaCO3
(C) Li, Ph − NH2 (D) H2 , Pt
27. In following reaction A and B respectively are: 32. Which of the following cannot be obtained when
alkenes are oxidised with KMnO4 and then followed
by acid hydrolysis?
(A) alkanoic acids (B) alkanols
(C) alkanones (D) carbon dioxide
(A)
33. Which alkyne gives 3 - ethylhexane on catalytic
hydrogenation?
(B)

(A) (B)
(C)

(D) (C) (D)

28. Which of the following will decolorise alkaline KMnO4

solution? 34. The final major product (B) in following reaction is :
(A) C3 H8 (B) CH4
(C) CCl4 (D) C2 H4
29. Product B and C in given reaction are respectively: (A) (B)
OsO4 HIO4
2 − methylbut − 2 − ene ⎯⎯ ⎯
H2O2
→ A ⎯⎯→ B+C

(A)
(C) (D)

(B)

(C)

(D)

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35. In following reaction if (B) and (C) both give + ve 39. Choose the major product of the follolwing reaction.
iodoform test then compound (A) can be:

(A) CH3 − CH = CH − O − CH2 − CH3

(A) (B)
(B)

(C) (C) (D)

40. Silver mirror test with Tollens reagent is given by:

(D) CH2 = CH − O − CH2 − CH3 (A) C6 H5 CHO
(B) Ph − NH − OH
36. Which of the following can be selectively oxidised by (C)
MnO2 /Δ :
(A) C6 H5 − CHOH − CH3
(B) C6 H5 − CH2 − CH2 − OH (D) CH3 CHO
(C) CH3 − CH = CH − CH2 − OH
(D) CH2 = CH − CH2 − CH2 − OH 41. Major product of following reaction is:
37. Which will give silver mirror test with Tollens reagent:
(A) C6 H5 CHO (B) CH3 − CHO
(C) HCOOH (D) C6 H5 CH(OH)COC6 H5
38. Fehling solution gives red precipitate with:
(A) Aromatic aldehyde (B) Aliphatic aldehyde (A) Ph − CH2 OH (B) NHMe2
(C) Ph − CH2 − NMe2 (D) Ph − CHO
(C) Ketones (D)

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EXERCISE – II 5. Which of the following compound will give positive

1. In which of the following reactions reactant and Tollens test
product both can show stereoisomerism:
(A) Tartaric acid (B)
(A)
(C) CH CH CH CH CH − OCH
3 2 2 2 3
|
OH
(B)
(D)

(C) 6. Which of the following reactions is/are correctly

match with their major products?

(D) (A)

2. Which of the following is an example of oxidation

reaction:
PCl3
(A) CH3 − CH2 − OH ⟶ (B)
Ni/H2
(B) CH3 − CH = CH2 ⟶
Br2
(C) CH3 − CH = CH2 ⟶
CCl4
DMSO/NaHCO3
(D) CH3 − CH2 − Cl ⟶
(C)
3. In following reaction sequence compound B is:

(D)

CHO 7. Which one of the following alcohols are oxidised by

|
(A) CHO (B) CH3 − CHO MnO2 ?
(C) CH3 − COOH (D) H − COOH (A) C6 H5 − CH2 − CH2 − OH

4. Major product of which reaction can show

Stereoisomerism? (B)
PCC
(A) C6 H5 − CH = CH − CH2 − OH ⟶
(C)
(B) (D) CH3 − CH2 − CH2 − OH
8. Which will give the Tollen test.

(C) C6H5 − CH = CH − CH2 − CH − CH2 − OH ⎯⎯⎯⎯⎯

TsCl
DMSO,NaHCO3
→ (A) (B)
|
CH3

(D)

(C) (D)

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9. Major product and reactant of which reactions gives

positive tollens test: (A) (B)
(A)

(C) (D)
(B)

14. Column-I Column-II

(Conversion) (Required Reagent)
(C)
(A) (P) H2 , Pd − BaSO4
HIO4
(D) OHCCH2OH ⎯⎯→
 (B) (Q) Li, Liq. NH3
10. In following reaction P and Q are respectively. (C) H3 C − CH = CH − CH3 ⟶ (R) N2 H4 /H2 O2
H3 C − CH2 − CH2 − CH3

(D) (S) B2 H6 , CH3 COOH

(A) Acetone and Hexane-1,2,5,6-tetraol.
(B) Acetaldehyde and Acetone.
(C) Acetaldehyde and Hexane-1,2,5,6-tetraol. 15. Total number of alcohols obtained in following
(D) Acetone and Formaldehyde. reaction is:

11. Choose the incorrect option(s) for following

sequence.

16. Total numbers of reagent that can be used for given

(A) P is a racemic compound conversion.
(B) Q is terminal alkyne
(C) X & R are positional isomer
(D) Formation of R is redox reaction
(a) Zn − Hg/HCl (b) LiAlH4
12. Which of the following compounds will consume even ⊖

number of periodic acid? (c) LiBH4 (d) (i) N2 H4 (ii) OH, Δ

(e) LiAl(OEt)3 H (f) Red P/HI
(A) HO − CH2 − CH2 − CH − CH2 − OH
(g) (i) (CH2 SH)2 (ii) H2 , Raney Ni
|
OH
COMPREHENSION TYPE Paragraph for Q. 17 to 21
(B) CH — CH − CH − CH
2 2
| | | |
OH OH OH OH
(C) H C — CH − CH − CH
2 3
| | |
OH OH OH 17. The compound (C) is:
(D) Me − C − CH − Me
|| | (A) (B)
O NH2
13. Which of the following is correctly matched?
(C) Et−≡ −Et (D) Both (A) and (B)
18. The compound (F) is:

(A) (B)

(C) Et−≡ −Et (D) Both (A) and (B)

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19. The compound (D) is:

(A) (B)

(C) (D) Both (B) and (C)

20. The compound (G) is:

(A) (B)

(C) (D) None of these

21. The compound (E) is:

(A) (B)
(C) One mole of (A) and one mole of (B) (D) No reaction.
22. Reaction of 2-butanol with Cu, Δ involve
(A) dehydrogenation (B) elimination
(C) dehydration (D) oxidation
23. Which of the following will give syn addition?

(A) (B)

(C) (D)

SUBJECTIVE TYPE
24. Complete the following reactions:

(a) (b) (c)

25. Complete the following reactions:

26. How many alkene on catalytic reduction give normal butane as product.
H2 /Pt H2 /Pt H2 /Pt
(i) (A) ⟶ n-butane (ii) (B) ⟶ Iso-pentane (iii) (C) ⟶ Neo-pentane
H2 /Pt H2
(iv) (D) ⟶ Cyclopentane (v) (E) ⟶
Pt

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27. Give the expected major product for each reaction, including stereochemistry where applicable.

28. Give product in the following reactions

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EXERCISE – III (JEE MAIN & ADVANCED) 8. The major product ' X ' formed in the following
1. The most suitable reagent for the conversion of R − reaction is: [JEE MAIN 2019]
CH2 − OH → R − CHO is [JEE MAIN 2014]
(A) CrO3
(B) PCC (Pyridinium chlorochromate)
(C) KMNO4
(D) K 2 Cr2 O7
2. Consider all possible isomeric ketones including (A) (B)
stereoisomers of MW = 100, All these isomers are
independently reacted with NaBH4
(NOTE: stereoisomers are also reacted separately)
The total number of ketones that give a racemic (C) (D)
product(s) is/are. [JEE MAIN 2014]
3. In the reaction [JEE MAIN 2014] 9. The product of the following reaction is:
AlCKOH
LiAlH4 PCl5
CH3 COOH ⟶ A ⟶ B ⟶ C. Final Product C is. [JEE MAIN 2019]
(A) H2 / Lindlar Cat. (B) Cat. hydrogenation
(C) LiAlH4 (D) Li/NH3
4. The reagent needed for converting is: (A)

(B)
[JEE MAIN 2014] (C)
(A) H2 / Lindlar Cat. (B) Cat. hydrogenation
(C) LiAlH4 (D) Li/NH3
(D)
5. Reagent(s) which can be used to bring about the
following transformation is(are): [JEE MAIN 2016] 10. The major product of the following reaction is:
[JEE MAIN 2019]

(A) LiAlH4 in (C2 H5 )2 O (B) BH3 in THF

(C) NaBH4 in C2 H5 OH (D) Raney Ni/H2 in THF (A) (B)
6. The major product obtained in the following reaction
is: [JEE MAIN 2017]
(C) (D)

11. The major product obtained in the following reaction

is: [JEE MAIN 2019]
(A) (B)

(C) (D) (A) (B)

7. The major product of following reaction is:

(1)AlH(i−Bu2 )
R−C≡N ⟶ [JEE MAIN 2019]
(2)H2 O (C) (D)
(A) RCHO (B) RCOOH
(C) RCH2 NH2 (D) RCONH2
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12. Which of the following compounds reacts with

ethylmagnesium bromide and also decolourizes (C)
bromine water solution [JEE MAIN 2019]

(D)
(A) (B)
16. The major product of the following reaction is:
[JEE MAIN 2019]

(C) (D)

13. The major product of the following reaction is:

[JEE MAIN 2019]
(A) (B)

(C) (D)
(A) (B)

17. The major product of the following reaction is:

[JEE MAIN 2019]
LiAlH4
(C) (D) CH3 CH = CHCO2 CH3 →
(A) CH3 CH2 CH2 CHO (B) CH3 CH2 CH2 CO2 CH3
(C) CH3 CH = CHCH2 OH (D) CH3 CH2 CH2 CH2 OH
14. The major product of the following reaction is: 18. Which of the following is NOT a correct method of the
[JEE MAIN 2019] preparation of benzylamine from cyanobenzene?
[JEE MAIN 2019]
(A) H2 /Ni (B) (i) HCl/H2 O (ii) NaBH4
(C) (i) LiAlH4 (ii) H3 O+ (D) (i) SnCl2 + HCl (gas)
(ii)NaBH4
19. Hex-3-ynal
(1)NaBH4 ( ) 3 ( )
2 PBr ( ) 2 ( )
3 Mg/Ether 4 CO 5 H
(A) (B) ⎯⎯⎯⎯ →⎯⎯⎯ →⎯⎯⎯⎯ →⎯⎯⎯ →⎯⎯⎯ →
(X), formed product X will be: [JEE MAIN 2020]

(C) (D) (A)

15. The major product(s) obtained in the following

reaction is/are: [JEE MAIN-2019] (B)

(C)

(A) (D)
(B)

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23. The most suitable reagent for the given conversion is:
20. Consider the following reactions [JEE MAIN 2020]
[JEE MAIN 2020]
'A' ⎯⎯⎯⎯
Ozonolysis
→ 'B'+ 'C'
(C6H14 )

(A) H2 , Pd (B) B2 H6
(A) (C) NaBH4 (D) LiAlH

(B) 24. In the reaction given below, the total number of atoms
having sp2 hybridization in the major product P is___.
[JEE ADVANCED 2021]
(C)

(D)
25. The major products A and B in the following set of
21. Reagent used for the given conversion is: reactions are: [JEE-MAIN 2021]
[JEE-MAIN 2020]

(A)

(B)

(C)

(A) H2 , Pd (B) B2 H6
(C) NaBH4 (D) LiAlH4
(D)
22. Three isomers A, B and C( mol. formula C8 H11 N) give
the following results [JEE MAIN 2020]
Diazotization
A and C → 26. If the reaction sequence given below is carried out
(i)Hydrolysis with 15 moles of acetylene, the amount of the product
(ii)Oxidation (KMnO4 +H+ ) R(ProductofA) D formed (in g ) is_____. [JEE ADVANCED 2022]
P+Q → +
S(ProductofC)
R has lower boiling point than S
C6 H5 SO2 Cl
B→ alkali-insoluble product
A, B and C, respectively are

The yields of A,B,C and D are given in parentheses.

[Given: Atomic mass of H = 1, C = 12, O = 16, Cl = 35]
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27. The number of −CH2 - (methylene) groups in the product formed from the following reaction sequence is______.
[JEE ADVANCED 2022]

28. The major products obtained from the reactions in List-II are the reactants for the named reactions mentioned in List-I.
Match List-I with List-II and choose the correct option. [JEE ADVANCED 2023]
List-I List-II
Zn−Hg,HCl
(P) Etard reaction (1) Acetophenone →
(i) KMnO4 ,KOH,Δ
(Q) Gattermann reaction (2) Toluene →
(ii) SOCl2
CH3 Cl
(R) Gattermann-Koch reaction (3) Benzene →
anhyd. AlCl3

NaNO2 /HCl
(S) Rosenmund reduction (4) Aniline →
273-278 K
Zn,Δ
(5) Phenol ⟶
(A) P → 2; Q → 4; R → 1; S → 3 (B) P → 1; Q → 3; R → 5; S → 2
(C) P → 3; Q → 2; R → 1; S → 4 (D) P → 3; Q → 4; R → 5; S → 2
29. Identify the reagents used for the following conversion [JEE MAIN 2024]

(A) A = LiAlH4 , B = NaOH(aq) , C = NH2 − NH2 /KOH, ethylene glycol

(B) A = LiAlH4 , B = NaOH(alc) , C = Zn/HCl
(C) A = DIBAL-H, B = NaOH(aq) , C = NH2 − NH2 /KOH, ethylene glycol
(D) A = DIBAL − H, B = NaOH(alc) , C = Zn/HCl

30. [JEE MAIN 2024]

This reduction reaction is known as:

(A) Rosenmund reduction (B) Wolff-Kishner reduction
(C) Stephen reduction (D) Etard reduction

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ANSWER KEY
EXERCISE – I
1. D 2. A 3. C 4. D 5. C 6. AC 7. A 8. C
9. B 10. AC 11. C 12. C 13. C 14. C 15. C 16. B
17. C 18. D 19. AC 20. D 21. D 22. C 23. C 24. C
25. A 26. B 27. B 28. D 29. A 30. C 31. C 32. B
33. ABCD 34. B 35. BC 36. AC 37. ABCD 38. BD 39. D
40. ABCD 41. C
EXERCISE – II
1. C 2. CD 3. D 4. ACD 5. ABC 6. ABCD 7. C
8. ACD 9. D 10. A 11. ABC 12. C 13. AB
14. (A)→P,R,S; (B)→Q; (C)→R,S; (D)→Q 15. 4 16. 4 17. A 18. B 19. A
20. BC 21. A 22. ABD 23. ABC

24.

25. (a) Ph– CH2 – CHO; (b) (C)

26. (i) Cis & trans 2-butene & 1-butene;

(ii)

(iii) Zero (Neo-pentane cannot be prepared by catalytic hydrogenation of alkene);

(iv) One

(v) Including optical = 4 , Excluding optical = 3

27.

28.

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EXERCISE – III (MAIN & ADVANCED)

1. B 2. 5 3. A 4. D 5. CD 6. C 7. A 8. B
9. A 10. B 11. B 12. C 13. B 14. B 15. A 16. B
17. C 18. B 19. A 20. B 21. B 22. D 23. B 24. 12
25. 0 26. 136 27. 0 28. D 29. D 30. A

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SOLUTION
EXERCISE – III (MAIN & ADVANCED)
2. M. wt 100 of ketone
So m, formula = C6 H12 O
1.

2.

3.

4.

5.

6.

7.

(1 : 2 : 3 : 6 : 7 )

3.
Reduction of CH3 COOH will produce CH3 – CH2 – OH(A) Now reaction of CH3 – CH2 – OH(A) with PCl5 will produce
CH3 – CH2 – Cl(B). Now alcoholic KOH with Et–Cl will produce CH2 = CH2 (C) Ethylene by E2 elemination. Thus Ans. is
(1) Ethylene.

19.

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20.

21. B2 H6 is very selective and usually used to reduce acid to alcohol

22.

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23. B2 H6 is very selective and usually used to reduce acid to alcohol.

24.

The total number of atoms having sp2 hybridization in the major product (P) = 12
This includes 4 C-atoms, 4 N-atoms and 4 O-atoms.

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25.

26.

27.

29.

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30.

It is known as rosenmund reduction that is the partial reduction of acid chloride to aldehyde

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