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Hydrocarbon Reactions and Transformations

The document outlines various chemical reactions involving alkanes, alkenes, alkynes, and aromatic hydrocarbons, detailing the reagents, processes, and functions of each reaction. It includes methods for hydrogenation, halogenation, oxidation, and polymerization, among others. Each reaction is categorized by its type and provides specific conditions and outcomes for converting different organic compounds.

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0% found this document useful (0 votes)
7 views14 pages

Hydrocarbon Reactions and Transformations

The document outlines various chemical reactions involving alkanes, alkenes, alkynes, and aromatic hydrocarbons, detailing the reagents, processes, and functions of each reaction. It includes methods for hydrogenation, halogenation, oxidation, and polymerization, among others. Each reaction is categorized by its type and provides specific conditions and outcomes for converting different organic compounds.

Uploaded by

ytmusic9103
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

REAGENTS PROCESS FUNCTION

PREPARA
TION DRAWING

1 Ni/Pd/Pt + H2 Hydrogenation Alkene into Alkane

2 Ni/Pd/Pt + 2H2 Hydrogenation Alkyne into Alkane

3 Zn,H+ + H2 [H+--->[Link]] Alkyl halides into Alkane [Except Fluorides]

(i)2Na + dry ether(or)dry ethereal [free from


Wurtz reaction Alkyl halides into Alkane
moisture]

(ii)Na + R-X + dry ether (Haloalkanes and


4 Wurtz-Fittig reaction Halobenzene into Alkylbenzene
Haloarenes lesson)

Alkane

(iii)2Na+ dry ether (Haloalkanes and


Fittig reaction Halobenzene into Diphenyl
Haloarenes lesson)

5 NaOH+CaO--->Sodalime Decarboxylation Sodium salt of Carboxylic acid into Alkane

[Link] of Sodium or Potassium Salt of a


6 2H2O+Electrolysis Kolbe's electrolytic method
carboxylic acid into Alkane

carbonyl compound like aldehydes and ketones only into


7 Zn-Hg(zinc amalgam)+HCl Clemmenson reagent
Alkane

carbonyl compound like aldehydes and ketones only into


8 (1)H2N-NH2-->hydrazine (2)KOH Wolff Kishner Reduction
Alkane
(i) X2+hν(or)UV(or)higher temperature[573-
Halogenation Alkane into Alkyl halides
773k].[X-->Cl , Br]

Halogenation (halides does


(ii) X2+hν(or)UV(or)higher temperature[573- Cyclohexane or Cyclohexene into Halide cyclohexane or
not break double bond in
773k].[X-->Cl , Br] Halide Cyclohexene
Cycloalkene )

10 ((3n+1)/2) O2 Combustion Alkane into carbondioxide and water CnH2n+2 + ((3n+1)/2) O2 → nCO2 + (n+1) H2O

11 O2+Cu573K(100 atm.) Controlled Oxidation Alkane into Alcohols

12 O2+Mo2O3(heat) Controlled Oxidation Alkane into Aldehyde group


Alkane
into
other
product
13 3O2+(CH3COO)2Mn+heat Controlled Oxidation Alkane into Carboxylic acid

14 KMnO4(oxidation) Controlled Oxidation Alkane into Alcohols

15 Anhy.AlCl3+HCl Isomerisation n-Alkane into Branching Alkane

n-Alkane(minimum n-hexane) into Benzene+higher


16 Cr2O3 or V2O5 or Mo2O3 (773k,10-20 atm) Aromatization or Reforming
carbon

17 Above773k heat(high temperature) Pyrolysis or Cracking Higher Alkane into lower Alkane or Alkene

Partially deactivated
H2+Pd/C with partially posion like Sulphur Alkyne into cis-Alkene (Ethene and Propene cannot form
18 Palladised Charcoal called
compound or Quinoline(C9H7N) cis or trans geometry isomerism
Lindlar's Catalyst
19 H2+Na/liq.NH3 Alkyne into trans-Alkene

Dehydrohalogenation and
Alkene 20 [Link](potassium ethoxide) Alkyl halides into Alkene (X=Cl,Br,I)
also β-elimination reaction

21 Zn Dehalogenation (Vicinal dihalides)Alkane into Alkene

Acidic dehydration of
22 Conc.H2SO4+heat alcohols and also β- Alcohol into Alkene
elimination reaction

Addition of Halogen and also


23 [Br2+CCl4 ]or [Cl2] Electrophilic addition Alkene into (Vicinal dihalides)Alkane
reaction

Addition of hydrogen halides


24 HCl or HI and also Electrophilic Alkene into Alkyl halides
addition reaction

Addition of hydrogen halides


25 HBr and also Electrophilic (Symmentry)Alkene into Alkyl halides
addition reaction

Addition of hydrogen halides


26 HBr or HI (Markovnikov rule) and also Electrophilic (Unsymmentry)Alkene into Alkyl halides
addition reaction

HBr+(C6H5CO2)2O2-->Peroxide. Addition of hydrogen halides


27 [AntiMarkovnikov rule or peroxide effect or and also Electrophilic (Unsymmentry)Alkene into Alkyl halides
Kharash effect] addition reaction

cold conc.H2SO4 or HOSO2OH (Markovnikov


28 Addition of sulphuric acid (Unsymmentry)Alkene into Alkyl hydrogen sulphate
rule)
Alkene
into
other
product
Addition of water or By Acid
29 H2O+H+[H+-->conc.H2SO4] (Markovnikov rule) Alkene into Alcohol
Catalysed hydration
H2O+O+[Link].KMnO4 , 273k.
30 Oxidation Alkene into Vicinal glycols
[[Link].KMnO4--> Baeyer's reagent]

31 KMnO4+H+[H+-->acid] Oxidative cleavage of alkenes Alkene into Ketones or acid depend on nature of Alkene

32 (1)O3 (2)Zn+H2O Ozonolysis Alkene into Aldehyde or Ketone + Aldehyde

[trace amount of O2(dioxide) or


(R)2O2(peroxide)]--> catalyst + high
33 temperature and high pressure . Example of Polymerisation Alkene into low density polymer
peroxide , H2O2 or (C6H5CO2)2O2 . It only
example, not used in this reaction.

[C6H15Al(triethylaluminium) or TiCl4(titanium
34 tetrachloride )] -->Ziegler-Natta catalyst + Polymerisation Alkene into high density polymer
low temperature and pressure

CaC2+2H2O. (CaC2{Calcium carbide} is


35 prepared by CaCO3 + heat give CaO + CO2. From Calcium carbide Calcium carbide with water into Ethyne
And then CaO + 3C gives CaC2 + CO.)
Alkyne

(1)[Link] + loss of KBr and H2O.


36 Dehydrohalogenation (Vicinal dihalides)Alkane into Alkyne
(2)NaNH2(sodamide) + loss of NaBr and NH3.

37 NaNH2-->Sodamide Alkyne into Sodium Alkynide

38 (1)Ni/Pd/Pt + H2 . (2)H2 Addition of Dihydrogen Alkyne into Alkene into Alkane

Alkyne into (Vicinal dihalides)Alkene into Alkane


(1)Br-Br+CCl4 . (2)Br-Br+CCl4 (CCl4--> Carbon
39 Addition of Halogen [remember that Alkane have 2 Vicinal dihalides or 2
tetrachloride)
Gem dihalides. So don't name any . Only name Alkane]

Alkyne
into
40 (1)HBr . (2)HBr Addition of Hydrogen halides Alkyne into (Gem dihalides) Alkane
other
product
(1)H2O+Hg2+/dil.H+ at 333k. [Hg2+-->mercuric Alkyne into Alcohol into Carbonyl compound like
Addition of Water
41 sulphate HgSO4 , H+-->H2SO4 sulphuric acid.] {Aldehyde only for Ethyne or (Unsymmentry
(Markovnikov rule)
(2) Isomerisation Alkyne)Ketone}

42 under suitable condition Linear polymerisation Ethyne into Polyacetylene or Polyethyne

43 Red hot iron(Fe) tube at 873k Cyclic Polymerisation (minimum 3 Alkyne)Alkyne into Benzene

Decarboxylation of Aromatic
44 NaOH+CaO--->Sodalime+heat Sodium salt of Benzoic Acid or Benzoic acid into Benzene
Acids
Aromatic
Hydrocar
bon
45 heated [Link]+Vapour Reduction of Phenol Phenol into Benzene

46 Conc.H2SO4+Conc.HNO3 at 323-333k Nitration Benzene into Nitrobenzene

47 anhy.AlCl3 or FeCl3 or FeBr3-->Lewis acid + Cl2 Halogenation Arenes into Haloarenes

H2SO4(SO3) or H2O7S2-->Fuming Sulphuric


48 Sulphonation Benzene into Benzene sulphonic acid
acid or Oleum

Friedel Crafts Alkylation


49 R-Cl or Alkyl halides + anhyd.AlCl3 Benzene into Alkylbenzene
reaction

Friedel Crafts Acylation


50 R-COX+ anhyd.AlCl3 (Lewis acid)+ heat Benzene into Acyl benzene
reaction
Acyl-O-Acyl or R-C-O-C-R or (R-CO)2O
Friedel Crafts Acylation
51 . ǁ ǁ Benzene into Acyl benzene and Carboxylic acid
reaction
Aromatic . O O
into
other
product
Friedel Crafts Acylation
52 6Cl2+ anhyd.AlCl3 + dark , cold Benzene into Hexachlorobenzene(C6Cl6)
reaction

53 high temperature and pressure + Ni + 3H3 Hydrogenation Benzene into Cyclohexane

54 UV + 500k + 3Cl2 Gammaxane Benzene into Benzene hexachloride(BHC)

[AlCl4]- (in case of Halogenation , alkylation


55 Removal of Proton Restore of Aromatic compound
and Acylation)

56 [HSO4]- (Nitration) Removal of Proton Restore of Aromatic compound

Aromatic compoun(Benzene) into Carbondioxide and


57 (X+Y/4)O2 Combustion
water

[HCl + ZnCl2] or [HCl+heat-->Retention in


58 Lucas reagent Alcohol into Haloalkanes
Haloalkane and Haloarenes]

59 NaBr + H2SO4 acid-base reaction Alcohol into Haloalkanes

60 PX3(Phosphorus halids) (X3-->Cl,Br) Alcohol into Haloalkanes


61 PCl3 Alcohol into Haloalkanes

Haloakanes

62 red P/X2 (X2-->Br2,I2) Alcohol into Haloalkanes

63 SOCl2-->Thionyl chloride Alcohol into Haloalkanes

Halogen Exchange and


64 NaI in dry Acetone Alkyl halides(X-->Cl,Br) into Alkyl Iodides
Finkelsten reaction

AgF or Hg2F2 or CoF2 or SbF3-->Metallic Halogen Exchange and


65 Alkyl halides(X-->Cl,Br) into Alkyl Fluoride
fluoride Swarts reaction

X2(Cl,Br)+Fe or Fe3Cl+dark . In case we


Electrophilic substitution of Arenes into (ortho or
substitute Iodine in X2 then it reversible. So Hydrocarbon by Electrophilic
66 para)Aryl halides (X-->Cl,Br) [Arenes fromula --> CnH2n-6m
required Oxidising agent (HNO3 or HIO4) to substitution
, [Link]]
Oxidize HI. F not react.

Amines by Sandmeyer's
(1) NaNO2 + HX at 273-278k (2) Cu2X2 (X-- Primary Aromatic amine into Diazonium salt into Aryl
Haloarenes 67 reaction or Diazonium salt
>Cl,Br) halide (X-->Cl,Br)
reaction

Amines by Sandmeyer's
Primary Aromatic amine into Diazonium salt into Aryl
68 (1) NaNO2 + HX at 273-278k (2) KI (X-->I) reaction or Diazonium salt
halide (X-->I (Iodine)
reaction

Nucleophilic substitution of
69 NaOH or KOH (SN2) Alkyl Halides into Alcohol
Alkyl Halides

Nucleophilic substitution of
70 H2O (SN1) Alkyl Halides into Alcohol
Alkyl Halides
Nucleophilic substitution of
71 NaOR' (SN2) Alkyl Halides into Ether
Alkyl Halides

Nucleophilic substitution of
72 NH3 (SN1) Alkyl Halides into Primary amine
Alkyl Halides

Nucleophilic substitution of
73 R'NH2 (SN1) Alkyl Halides into Secodary amine
Alkyl Halides

Nucleophilic substitution of
74 R'R''NH (SN1) Alkyl Halides into Tertiary amine
Alkyl Halides

Nucleophilic substitution of
75 KCN (SN2) Alkyl Halides into Nitrile (cyanide)
Alkyl Halides

Reaction
on Nucleophilic substitution of
76 AgCN (SN2) Alkyl Halides into Isonitrile (Isocyanide)
Haloalka Alkyl Halides
ne

Nucleophilic substitution of
77 KNO2 (SN2) Alkyl Halides into Alkyl nitrite
Alkyl Halides

Nucleophilic substitution of
78 AgNO2 (SN2) Alkyl Halides into Nitroalkane
Alkyl Halides

Nucleophilic substitution of
79 R'COOAg (SN2) Alkyl Halides into Ester
Alkyl Halides

Nucleophilic substitution of
80 LiAlH4 (SN2) Alkyl Halides into Hydrocarbon
Alkyl Halides
Nucleophilic substitution of
81 R'-M (M-metal) (SN2) Alkyl Halides into Alkane
Alkyl Halides

82 Mg + dry ether Grignard reagent Alkyl halide into Alkyl magnesium halide

(1)Mg + dry ether (2)H2O(water) or OH- Alkyl halide into Alkyl magnesium halide into
83
(Alcohol) or [-NH2 or >NH or >N-] (Amine) Hydrocarbon

Replacement by Hydroxyl
(i) NaOH , 623k, 300 atm (ii) HꚚ group and Down process Chlorobenzene into Phenol
reaction

Replacement by Hydroxyl
84 (ii) NaOH , 443k, 300 atm (ii) HꚚ group and Down process 1-Chloro-4-nitrobenzene into 4-nitroPhenol
reaction

Replacement by Hydroxyl
(iii) NaOH , 368k, 300 atm (ii) HꚚ group and Down process 1-Chloro-2,4-nitrobenzene into 2,4-nitroPhenol
reaction

Replacement by Hydroxyl
85 H2O + warm 1-Chloro-2,4,6-nitrobenzene into 2,4,6-nitroPhenol
group

Haloaren
es into Chlorobenzene into 1,4-dihalobenzene (major - para) or
86 Cl2 + Anhyd. FeCl3 Halogenation
other 1,2-dihalobenzene ( minor-ortho)
product

Chlorobenzene into 1-Halo-4-nitrobenzene(major - para)


87 Conc.H2SO4+Conc.HNO3 at 323-333k Nitration
or 1-Halo-2-nitrobenzene(minor-ortho)

Chlorobenzene into 4-Halobenzenesulfonic acid(major-


88 Conc.H2SO4 Sulphonation
para) or 2-Halobenzenesulfonic acid(minor-ortho)

Chlorobenzene into 1-Halo-4-alkylbenzene(major-para)


89 R-Cl + Anhyd.AlCl3 Friedel-crafts reaction
or 1-Halo-2-alkylbenzene(minor-ortho)
H3C-C-Cl + Anhyd.AlCl3
Chlorobenzene into 4-Haloacetophenone(major-para) or
90 . ǁ Friedel-crafts reaction
2-Haloacetophenone(minor-ortho)
. O

(1)(H-BH2 )2 (2) R-CH=CH2 (3)R-CH=CH2 (4) Alkene into Alcohol(Alkene into Alkane bond with BH2
Hydroboration-Oxidation
91 [H2O + ŌH]-->[Link] hydroxide(NaOH-- into (Alkane)2 bond with BH into (Alkane)3 bond with B
(Anti-Morkovink rule)
>Na+ŌH) + 3H2O2 into Alcohol + Boric acid

By Reduction of Aldehydes Aldehyde into Primary Alcohol and Ketone into


92 Ni/Pd/Pt + H2 (Hydrogenation)
and Ketones secondary Alcohol

By Reduction of Aldehydes Aldehyde into Primary Alcohol and Ketone into


93 NaBH4
and Ketones secondary Alcohol

Preparati
by Reduction of Carboxlic
on of 94 (i)LiAlH4 (ii)H2O (Expensive reagent) Carboxylic acid or esters into primary Alcohol
acid and esters
Alcohol

Carboxylic acid into ester into primary Alcohol


(1) R'OH + H+ [H+--->H2SO4] (2)[H2 + catalyst ] by Reduction of Carboxlic
95 (Carboxylic acids can react with alcohols to form esters
--> Hydrogenation acid and esters
in a process called Fischer esterification)

Aldehyde into Adduct into Secondary Alcohol (exception


96 (1) R'-Mg-X (2) H2O Grignard reagent
Formaldehyde or Methanal give primary Alcohol)

97 (1) R'-Mg-X (2) H2O Grignard reagent Ketone into Adduct into Tertiary Alcohol

From Haloarenes and


98 (1)NaOH at 623k and 320 atm (2) HCl Downprocess (commercial Chlorobenzene into Sodium phenoxide into Phenol
preparation)

From Cumene (commerical Cumene (Isopropylbenzene) into Cumene hydroperoxide


99 (1) O2 (2) H+ + H2O
preparation) into Phenol and Acetone
Preparati
on of
(1)H2SO4(SO3) or H2O7S2-->Fuming Sulphuric
Phenol Benzene into Benzene sulphonic acid into Sodium
acid or Oleum (2) NaOH and loss of water
From Benzenesulphonic acid Benzene sulphonate into Sodium phenoxide into Phenol
100 (3) Molten NaOH and loss of Na2SO3 and
(Lab preparation) (Elaborated). In Book , Benzene into Benzene sulphonic
water (4) HCl and loss of NaCl (Elaborated) .
acid into Phenol.
In Book , (1)Oleum (2) (i) NaOH (ii) H+
(1) [NaNO2 + HCl]--> Nitrous acid (2) H2O and From Diazonium salt (Lab Aromatic primary amine(Aniline) into Benzene
101
warm preparation) diazonium Chloride into Phenol

Cleavage of O-H bond and Alcohol into Sodium alkoxide and Phenol into Sodium
102 2Na
React with metal Phenoxide

Cleavage of O-H bond and


103 2Al tert-alkyl alcohol into Aluminium tert- alkyloxide
React with metal

Cleavage of O-H bond and


104 NaOH Phenol into Sodium Phenoxide
React with metal

Alcohol
and
Phenol Cleavage of O-H bond and
105 R'-COOH + H+ Alcohol or Phenol into ester
into Esterification
other
product

Cleavage of O-H bond and


106 (R'CO)2O + H+ Alcohol or Phenol into ester and carboxylic acid
Esterification

Cleavage of O-H bond and


107 R'COCl + Pyridine Alcohol or Phenol into ester
Esterification

Cleavage of O-H bond and Salicylic acid into Acetylsalicylic acid (Aspirin) and
108 (CH3CO)2O + H+
Acetylation ethanoic acid

HX (already in 58 reaction point . But in this Cleavage of C-O bond and


109 Alcohol into Alkyl halides
reaction HX only) react with Hydrogen halides

H2SO4 + heat 443k(already in 22 reaction Cleavage of C-O bond and


110 Alcohol into Alkene
point. Same reaction) Dehydration
Cleavage of C-O bond and
111 85% H3PO4 + 440k Secondary alcohol into Alkene
Dehydration

Cleavage of C-O bond and


112 20% H3PO4 + 358k Tertiary alcohol into Branched Alkene
Dehydration

Cleavage of C-O bond and


113 (1) K2Cr2O7 or KMnO4 (2) K2Cr2O7 or KMnO4 primary alcohol into Aldehyde into Carboxylic acid
Oxidation

Alcohol
into Cleavage of C-O bond and
114 CrO3 in anhydrous medium Primary alcohol into Aldehyde
other Oxidation
product

PCC --> Pyridinium Chlorochromate


Cleavage of C-O bond and
115 ([C5H5NH]+[CrO3Cl]− or [C5H5NH]+[CrO3Cl]− or primary alcohol into Aldehyde
Oxidation
chromium trioxide with pyridine and HCl)

Cleavage of C-O bond and


116 CrO3 secondary alcohol into Ketone
Oxidation

Cleavage of C-O bond and


117 Cu at 573k primary alcohol into Aldehyde
dehydration

Cleavage of C-O bond and


118 Cu at 573k Secondary alcohol into Ketone
dehydration

Cleavage of C-O bond and


119 Cu at 573k and loss of water Tertiary alcohol into Branched Alkene
dehydration

Electrophilic Aromatic Phenol into Nitrophenol ( both ortho and para produce
120 Dilute HNO3 at low temperature 298k
substitution and Nitration same time)
Electrophilic Aromatic
Br2 in [CS2 or CHCl3]--> Solvent of low polarity Phenol into monobromophenol (major-para , minior-
121 substitution and
at low temperature 273k ortho)
Halogenation

Electrophilic Aromatic
122 3Br2(aq.)--> Bromine water substitution and Phenol into 2,4,6-Tribromophenol
Halogenation

Phenol
into Phenol into sodium phenoxide into ortho
123 (1)NaOH (2) (i) CO2 (ii) H+ Kolbe's reaction
other hydroxybenzoic acid (Salicylic acid)
product

Phenol into Phenol with chloform into


124 (1) CHCl3 + aq NaOH (2) NaOH (3) H+ Reimer-Tiemann reaction salicyladehyde(but Na present) into salicyladehyde( H
present)

125 Zn ( same in 45 reaction point) Zinc dust Phenol into Benzene

126 Na2Cr2O7 + H2SO4 Oxidation Phenol into Benzoquinone

2H2+ Zn-Cr2O3 and 200-300 atm , 573-673k


127 Hydrogenation Carbonmonoxide into methanol (wood spirit)
(high temp. and pressure)
Commer
cially
importan
t Alcohol
C12H22O11 (Sucrose reffer table sugar or cane sugar) into
128 (1) H2O (Invertase) (2) Zymase Fermentation
Glucose into Ethanol and Carbondioxide

129 [H2SO4 or H3PO4 ]-->Protic acids at 443k Dehydration of Alcohol Alcohol into Alkene

130 [H2SO4 or H3PO4 ]-->Protic acids at 413k Dehydration of Alcohol Alcohol into Ether
Preparati
on of
on of
Ethers
Alkylhalide(Primary) into Ether. [Tertiary Alkylhalide
131 R'-O-Na+ Williamson Systhesis
doesn't give Ether. It give Alkene.]

Phenol into Sodium Phenoxide into Ether or Alkyl


132 (i) NaOH (ii)R-X Williamson Systhesis
Phenoxide

Cleavage of C-O bond in


133 HX Ether into Alkyl halide and Alcohol
Ethers

Cleavage of C-O bond in


134 HX Aromatic Ether into Phenol and Alkyl halide
Ethers

Cleavage of C-O bond in Alcohol into Alkyl halide and water (or)Phenol into Aryl
135 HX
Ethers halide(Aromatic halide) and water

Ether
into
Electrophilic substitution and Phenylalkyl ether into Bromo-Phenylalkyl ether [Eg:-
other 136 Br2 in Ethanoic acid or Acetic acid (CH₃COOH)
Halogenation Anisole into Bromoanisole (major-para , minor-ortho)]
compou
nd

Electrophilic substitution and


Phenylalkyl ether into p-alkyl Phenylalkyl ether (major)
137 R-Cl + Anhyd.AlCl3 + CS2 Friedel Crafts Acylation
or O-alkyl Phenylalkyl ether (minor)
reaction

R-COX+ anhyd.AlCl3 (Lewis acid)+ CS2 (already Electrophilic substitution and Phenylalkyl ether into p-ketone Phenylalkyl ether
138
in 50 reaction point) Friedel Crafts reaction (major) or O-ketone Phenylalkyl ether (minor)

Electrophilic substitution and Phenylalkyl ether into p-nitro Phenylalkyl ether (major)
139 H2SO4 + HNO3
Nitration or O-nitro Phenylalkyl ether (minor)

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