Chemistry · Organic Chemistry

Alcohols Phenols and Ethers formulas for JEE

Every Alcohols Phenols and Ethers formula you need for JEE, grouped by concept.

FormulasRevision notes
30 formulas2 concepts
01Alcohols, Phenols, and Ethers Properties02Reactions of Alcohols and Phenols
01

Alcohols, Phenols, and Ethers Properties

10 formulas

Grignard Addition to Methanal

HCHO+RMgX→RCH2OMgX→H2ORCH2OH+Mg(OH)XHCHO + RMgX \rightarrow RCH_2OMgX \xrightarrow{H_2O} RCH_2OH + Mg(OH)X

Preparation of primary alcohols from methanal (formaldehyde) and a Grignard reagent.

applies whenYields 1° alcohol.
preparationgrignardprimary-alcohol

Grignard Addition to Aldehydes

RCHO+R′MgX→RCH(R′)OMgX→H2ORCH(R′)OH+Mg(OH)XRCHO + R'MgX \rightarrow RCH(R')OMgX \xrightarrow{H_2O} RCH(R')OH + Mg(OH)X

Preparation of secondary alcohols from aldehydes (other than methanal).

applies whenYields 2° alcohol.
preparationgrignardsecondary-alcohol

Grignard Addition to Ketones

RCOR′+R′′MgX→R(R′)(R′′)COMgX→H2OR(R′)(R′′)COH+Mg(OH)XRCOR' + R''MgX \rightarrow R(R')(R'')COMgX \xrightarrow{H_2O} R(R')(R'')COH + Mg(OH)X

Preparation of tertiary alcohols from ketones.

applies whenYields 3° alcohol.
preparationgrignardtertiary-alcohol

Acid-Catalyzed Hydration of Alkenes

Alkene+H2O→H+AlcoholAlkene + H_2O \xrightarrow{H^+} Alcohol

Preparation of alcohols from alkenes following Markovnikov's rule.

applies whenFollows Markovnikov's rule, carbocation intermediate allows rearrangement.
preparationalkenehydration

Hydroboration-Oxidation of Alkenes

3R−CH=CH2→(BH3)2(R−CH2−CH2)3B→H2O2,OH−3R−CH2−CH2OH3 R-CH=CH_2 \xrightarrow{(BH_3)_2} (R-CH_2-CH_2)_3B \xrightarrow{H_2O_2, OH^-} 3 R-CH_2-CH_2OH

Preparation of alcohols from alkenes yielding anti-Markovnikov addition.

applies whenNo carbocation formed; no rearrangements.
preparationhydroborationanti-markovnikov

Reduction of Carboxylic Acids

RCOOH→(ii)H2O(i)LiAlH4RCH2OHRCOOH \xrightarrow[(ii) H_2O]{(i) LiAlH_4} RCH_2OH

Strong reduction of carboxylic acids to primary alcohols.

applies whenLiAlH4 is expensive, generally converted to esters first commercially.
preparationreductioncarboxylic-acid

Williamson Ether Synthesis

R−X+R′−O−Na+→SN2R−O−R′+NaXR-X + R'-O^-Na^+ \xrightarrow{S_N2} R-O-R' + NaX

SN2 reaction of an alkoxide with a primary alkyl halide.

applies whenAlkyl halide must be 1°. 2°/3° alkyl halides yield alkenes due to competing elimination.
preparationetherwilliamsonname-reaction

Commercial Preparation of Phenol (Cumene Process)

C6H5CH(CH3)2→O2C6H5C(CH3)2OOH→H+C6H5OH+CH3COCH3C_6H_5CH(CH_3)_2 \xrightarrow{O_2} C_6H_5C(CH_3)_2OOH \xrightarrow{H^+} C_6H_5OH + CH_3COCH_3

Air oxidation of cumene to cumene hydroperoxide, followed by acidic cleavage.

applies whenAcetone is a valuable by-product.
preparationphenolcumeneindustrial

Phenol from Diazonium Salts

C6H5N2+Cl−+H2O→WarmC6H5OH+N2+HClC_6H_5N_2^+Cl^- + H_2O \xrightarrow{\text{Warm}} C_6H_5OH + N_2 + HCl

Hydrolysis of benzene diazonium chloride to yield phenol.

applies whenAqueous warming conditions.
preparationphenoldiazonium

Dow Process for Phenol

C6H5Cl→320 atm,623 KNaOHC6H5ONa→H+C6H5OHC_6H_5Cl \xrightarrow[320 \text{ atm}, 623 \text{ K}]{NaOH} C_6H_5ONa \xrightarrow{H^+} C_6H_5OH

Preparation of phenol from chlorobenzene via nucleophilic aromatic substitution.

applies whenRequires extreme temperature and pressure.
preparationphenolhaloarene
02

Reactions of Alcohols and Phenols

20 formulas

Reaction of Alcohols with Sodium

2R−OH+2Na→2R−ONa+H2↑2 R-OH + 2 Na \rightarrow 2 R-ONa + H_2 \uparrow

Demonstration of acidic nature of alcohols.

applies whenActive metals like Na, K, Al.
reactionaciditymetal

Action of Heated Copper on Tertiary Alcohols

R3COH→573 KCuAlkene+H2OR_3COH \xrightarrow[573 \text{ K}]{Cu} \text{Alkene} + H_2O

Tertiary alcohols undergo dehydration instead of dehydrogenation when passed over heated Cu.

applies whenVapors passed over heated Cu at 573 K.
reactiondehydrationcatalytic

Acidic Dehydration to Alkene

CH3CH2OH→443 Kconc.H2SO4CH2=CH2+H2OCH_3CH_2OH \xrightarrow[443 \text{ K}]{conc. H_2SO_4} CH_2=CH_2 + H_2O

Intramolecular elimination of water from ethanol at high temperature.

applies whenHigh temperature (443 K), yields alkene.
reactiondehydrationelimination

Acidic Dehydration to Ether

2CH3CH2OH→413 Kconc.H2SO4C2H5OC2H5+H2O2 CH_3CH_2OH \xrightarrow[413 \text{ K}]{conc. H_2SO_4} C_2H_5OC_2H_5 + H_2O

Intermolecular dehydration of primary alcohols at lower temperatures to form ethers.

applies whenLower temperature (413 K), SN2 mechanism. Only valid for unhindered 1° alcohols.
reactiondehydrationsubstitutionether

Esterification of Alcohols

ROH+R′COOH⇌H+R′COOR+H2OROH + R'COOH \xrightleftharpoons{H^+} R'COOR + H_2O

Reaction of alcohols with carboxylic acids to form esters.

applies whenReversible; water must be continuously removed.
reactionesterification

Lucas Test Reaction

ROH+HCl→ZnCl2RCl+H2OROH + HCl \xrightarrow{ZnCl_2} RCl + H_2O

Reaction of alcohols with HCl in presence of zinc chloride to form alkyl chlorides.

applies whenDistinguishes 1° (no room temp reaction), 2° (5 mins), and 3° (immediate turbidity).
reactionlucas-testidentification

Mild Oxidation of Primary Alcohols

RCH2OH→PCC or CrO3RCHORCH_2OH \xrightarrow{PCC \text{ or } CrO_3} RCHO

Oxidation of primary alcohols to aldehydes using PCC or anhydrous CrO3.

applies whenPrevents over-oxidation to carboxylic acid.
reactionoxidationaldehyde

Oxidation of Secondary Alcohols

R2CHOH→CrO3R2C=OR_2CHOH \xrightarrow{CrO_3} R_2C=O

Oxidation of secondary alcohols to ketones.

applies whenChromic anhydride used as oxidizing agent.
reactionoxidationketone

Pinacol-Pinacolone Rearrangement

R2C(OH)−C(OH)R2→H+R3C−C(=O)R+H2OR_2C(OH)-C(OH)R_2 \xrightarrow{H^+} R_3C-C(=O)R + H_2O

Acid-catalyzed dehydration and rearrangement of a vicinal diol to a ketone.

applies whenInvolves carbocation formation and 1,2-alkyl shift.
reactionrearrangementjee-advanced

Cleavage of Alkyl Aryl Ethers

C6H5−O−CH3+HI→C6H5OH+CH3IC_6H_5-O-CH_3 + HI \rightarrow C_6H_5OH + CH_3I

Alkyl-oxygen bond cleavage occurs exclusively due to strong sp2 C-O bond in phenol.

applies whenPhenol does not react further with HI.
reactionethercleavageanisole

Claisen Rearrangement

C6H5−O−CH2−CH=CH2→Δo-HO-C6H4-CH2−CH=CH2C_6H_5-O-CH_2-CH=CH_2 \xrightarrow{\Delta} o\text{-}HO\text{-}C_6H_4\text{-}CH_2-CH=CH_2

Thermal rearrangement of an allyl phenyl ether to an o-allylphenol.

applies whenTakes place purely via heating (~200 C);-sigmatropic rearrangement.
reactionrearrangementetherjee-advanced

Ether Cleavage by Hydrogen Halides

R−O−R′+HX→R−X+R′−OHR-O-R' + HX \rightarrow R-X + R'-OH

Cleavage of ethers to alkyl halide and alcohol.

applies whenReactivity order: HI > HBr > HCl. With excess HX, both R groups become alkyl halides.
reactionethercleavage

Fries Rearrangement

C6H5OCOR→AlCl3,Δo/p-HO-C6H4-CORC_6H_5OCOR \xrightarrow{AlCl_3, \Delta} o/p\text{-}HO\text{-}C_6H_4\text{-}COR

Conversion of phenolic esters to corresponding hydroxyaryl ketones.

applies whenCatalyzed by Lewis acids like AlCl3.
reactionrearrangementphenoljee-advanced

Bromination of Phenol (Aqueous)

C6H5OH+3Br2→H2O2,4,6-tribromophenol↓+3HBrC_6H_5OH + 3Br_2 \xrightarrow{H_2O} 2,4,6\text{-tribromophenol} \downarrow + 3HBr

Reaction with bromine water yielding tribromophenol.

applies whenForms a white precipitate.
reactionphenolhalogenation

Kolbe's Reaction

C6H5ONa+CO2→H+o-Hydroxybenzoic acidC_6H_5ONa + CO_2 \xrightarrow{H^+} o\text{-Hydroxybenzoic acid}

Electrophilic aromatic substitution of phenoxide with carbon dioxide to form salicylic acid.

applies whenPhenoxide is more reactive than phenol, allowing weak electrophile CO2 to attack.
reactionphenolkolbename-reaction

Nitration of Phenol (Concentrated)

C6H5OH→conc. HNO3,conc.H2SO42,4,6-trinitrophenol (Picric Acid)C_6H_5OH \xrightarrow{\text{conc. } HNO_3, conc. H_2SO_4} 2,4,6\text{-trinitrophenol (Picric Acid)}

Formation of picric acid using concentrated acids.

applies whenModern method involves intermediate sulfonation to improve poor yield.
reactionphenolnitrationpicric-acid

Nitration of Phenol (Dilute)

C6H5OH+dil. HNO3→298 Ko-nitrophenol+p-nitrophenolC_6H_5OH + \text{dil. } HNO_3 \xrightarrow{298 \text{ K}} o\text{-nitrophenol} + p\text{-nitrophenol}

Electrophilic substitution yielding a mixture of ortho and para nitrophenols.

applies whenLow temperature. o-isomer is steam volatile due to intramolecular H-bonding.
reactionphenolnitration

Oxidation of Phenol

C6H5OH→Na2Cr2O7,H2SO4BenzoquinoneC_6H_5OH \xrightarrow{Na_2Cr_2O_7, H_2SO_4} \text{Benzoquinone}

Oxidation to a conjugated diketone using chromic acid.

applies whenSlow oxidation in air also yields dark mixtures of quinones.
reactionphenoloxidation

Reimer-Tiemann Reaction

C6H5OH→(ii)H+(i)CHCl3, aq. NaOHo-HydroxybenzaldehydeC_6H_5OH \xrightarrow[(ii) H^+]{(i) CHCl_3, \text{ aq. } NaOH} o\text{-Hydroxybenzaldehyde}

Reaction of phenol with chloroform and base yielding salicylaldehyde.

applies whenProceeds via a substituted benzal chloride intermediate.
reactionphenolreimer-tiemannname-reaction

Reduction of Phenol

C6H5OH+Zn→ΔC6H6+ZnOC_6H_5OH + Zn \xrightarrow{\Delta} C_6H_6 + ZnO

Cleavage of aromatic C-O bond by heating with zinc dust.

applies whenRequires heating.
reactionphenolreduction
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