Free NEET Chemistry multiple-choice questions on Alcohols & Phenols. Attempt each question and reveal the answer with a full explanation.
Reaction of phenol with chloroform in the presence of dilute sodium hydroxide introduces which functional group into the benzene ring? -CHO -COOH -CH 2Cl -Cl The major product formed when phenol is treated with concentrated HNO 3 in the presence of concentrated H 2SO 4 is: 2,4,6-Trinitrophenol p-Nitrophenol o-Nitrophenol Picramide Reaction of anisole with Br 2 in ethanoic acid gives mainly: p -Bromoanisole o -Bromoanisole 2,4,6-Tribromoanisole m -Bromoanisole H 2COH.CH 2OH on heating with periodic acid gives : 2 CO 2 2 HCOOH Consider the following reaction Ethanol PBr 3 X alc. KOH Y [ (ii) H 2O,Heat ] (i) H 2SO 4, room temperature Z; The product Z is : CH 3CH 2 - OH CH 2 = CH 2 CH 3CH 2 - O - CH 2CH 3 CH 3CH 2 - O - SO 3H Which of the following will not be soluble in sodium hydrogen carbonate? 2, 4, 6-trinitrophenol Benzoic acid o-Nitrophenol Benzenesulphonic acid Which of the following reagents would distinguish cis-cyclopentane-1,2-diol from the trans-isomer? Acetone Ozone MnO2 Aluminium isopropoxide The oxidation of phenol with chromic acid gives An aldehyde A simple diketone A Conjugated diketone Ortho benzoquinone Compound A, C8H10O , is found to react with NaOI (produced by reacting Y with NaOH ) and yields a yellow precipitate with characteristic smell. A and Y are respectively The compound that is most difficult to protonate is : The structure of intermediate A in the following reaction, is Given below are two statements Statement I: The acidic strength of monosubstituted nitrophenol is higher than phenol because of electron withdrawing nitro group. Statement II: o -nitrophenol, m -nitrophenol and p -nitrophenol will have same acidic strength as they have one nitro group attached to the phenolic ring. In the light of the above statements, choose the most appropriate answer from the options given below: Both Statement I and Statement II are incorrect. Statement I is correct but Statement II is incorrect. Statement I is incorrect but Statement II is correct. Both Statement I and Statement II are correct. Phenol is distilled with zinc dust to produce: Benzene Cyclohexane Benzophenone Toluene Consider the following reaction and identify the product (P). CH3 - CH3 | CH - OH | CH - CH3 ->[HBr] Product (P) 3-Methylbutan-2-ol CH3 - Br | CH3 | C - CH2 - CH3 CH3CH=CH-CH3 CH3 - CH3 | CH - Br | CH - CH3 CH3 - CH3 | CH3 | C - CH2Br In the following reaction sequence, X and Z respectively are : X = POCl3 ; Z = CH3 - Br | CH - CH3 X = POCl3 ; Z = CH3CH2CH2-Br X = H3PO3 ; Z = CH3 - Br | CH - CH3 X = H3PO3 ; Z = CH3CH2CH2-Br Match List I with List II: Choose the correct answer from the options given below : A-I, B-III, C-IV, D-II A-II, B-IV, C-III, D-I A-II, B-III, C-IV, D-I A-II, B-III, C-I, D-IV The correct order of acid strength of the following substituted phenols is: p-Nitrophenol > m-Nitrophenol > Phenol > p-Methylphenol Phenol > p-Nitrophenol > m-Nitrophenol > p-Methylphenol p-Methylphenol > Phenol > m-Nitrophenol > p-Nitrophenol p-Nitrophenol > Phenol > m-Nitrophenol > p-Methylphenol In the Fischer esterification of ethanoic acid with methanol, the oxygen atom in the water molecule formed comes from: The carboxylic acid group The alcohol group Both equally The catalyst Reaction of ethylene glycol with periodic acid ( HIO 4 ) gives: Two molecules of formaldehyde Glyoxal Oxalic acid Two molecules of formic acid When glycerol is heated with excess of HI , the final product obtained is: 2-Iodopropane 1,2,3-Triiodopropane Allyl iodide Propene When an alcohol 'A' is treated with PCl 5 , it gives 'B'. 'B' reacts with KCN to give 'C'. Hydrolysis of 'C' gives propanoic acid. 'A' is: Ethanol Methanol Propan-1-ol Propan-2-ol The rate of esterification of the following alcohols with acetic acid follows the order: CH 3OH > CH 3CH 2OH > (CH 3) 2CHOH (CH 3) 2CHOH > CH 3CH 2OH > CH 3OH CH 3CH 2OH > (CH 3) 2CHOH > CH 3OH All react at the same rate The Elbs persulfate oxidation of phenol involves the treatment of phenol with alkaline K 2S 2O 8 to introduce a hydroxyl group at which position? Para Ortho Meta Both Ortho and Para The treatment of phenol with CO 2 and NaOH followed by acidification gives salicylic acid. This reaction is known as: Kolbe's reaction Reimer-Tiemann reaction Wurtz reaction Etard reaction The pK a values of o-nitrophenol , m-nitrophenol , and p-nitrophenol follow the order: m-nitrophenol > o-nitrophenol > p-nitrophenol p-nitrophenol > o-nitrophenol > m-nitrophenol m-nitrophenol > p-nitrophenol > o-nitrophenol o-nitrophenol > p-nitrophenol > m-nitrophenol The major product formed in the reaction of 1-methylcyclohexene with B 2H 6 followed by oxidation with H 2O 2 in the presence of NaOH is: trans-2-methylcyclohexanol cis-2-methylcyclohexanol 1-methylcyclohexanol 2-methylcyclohexanone In the Fries rearrangement, a phenolic ester is converted into o - and p -hydroxy ketones. Which temperature condition favors the formation of the p -isomer as the major product? Low temperature ( < 60 C ) High temperature ( > 160 C ) Room temperature Temperature has no effect Which of the following alcohols will undergo oxidation with acidified KMnO 4 to produce a mixture of carboxylic acids with fewer carbon atoms? 2-Methylpropan-2-ol Propan-1-ol Butan-2-ol Ethanol In the Liebermann Nitroso test for phenols, the sequence of colors observed is: Brown Blue/Green Red Blue Red Brown Blue Blue Red Colorless Yellow Green Violet The major product formed when 3,3-dimethylbutan-2-ol is heated with concentrated H 2SO 4 is: 2,3-Dimethylbut-2-ene 3,3-Dimethylbut-1-ene 2,3-Dimethylbut-1-ene 2,2-Dimethylbut-2-ene The major organic product of the reaction between Phenol and Acetone in the presence of an acid catalyst is: Bisphenol A Aspirin Salol Phenolphthalein Which amongst the following will be most readily dehydrated under acidic conditions? One of the products formed in the following reaction is In the preparation of phenol from cumene, the intermediate formed upon oxidation with air is: Cumene hydroperoxide Cumene peroxide Acetone Benzene hydroperoxide What is the correct order of the ease of dehydration of the following alcohols in the presence of concentrated H 2SO 4 ? Tertiary > Secondary > Primary Primary > Secondary > Tertiary Secondary > Tertiary > Primary Tertiary > Primary > Secondary When ethanol is treated with sodium metal, a gas is evolved. This gas is: H 2 O 2 CO 2 C 2H 6 Reaction of phenol with bromine water gives a white precipitate of: 2,4,6-Tribromophenol o-Bromophenol p-Bromophenol m-Bromophenol Phenol reacts with dilute HNO 3 at 298 K to give a mixture of: o-Nitrophenol and p-Nitrophenol 2,4,6-Trinitrophenol m-Nitrophenol o-Nitrophenol only Which reaction is used for the preparation of p -Hydroxybenzaldehyde from phenol? Reimer-Tiemann Reaction Kolbe's Reaction Etard Reaction Stephen Reaction The reaction of propan-2-ol over heated copper catalyst at 573 K results in the formation of: Propanone Propanal Propene Propanoic acid In the presence of AlCl 3 , phenol reacts with CH 3COCl to give o - and p -hydroxyacetophenone. This is an example of: Friedel-Crafts Acylation Friedel-Crafts Alkylation Wurtz reaction Fittig reaction Which of the following is more acidic and why? Phenol, because of resonance stabilization of the phenoxide ion Cyclohexanol, because it is more stable Phenol, because it has more hydrogen atoms Cyclohexanol, because of the -I effect of the ring Which of the following has the highest boiling point? Butan-1-ol Butan-2-ol Diethyl ether n-Butane Which of the following isomeric alcohols is expected to have the highest solubility in water? n-butyl alcohol isobutyl alcohol sec-butyl alcohol tert-butyl alcohol The rearrangement of phenolic esters to o - and p -hydroxy ketones in the presence of anhydrous AlCl 3 is called: Fries Rearrangement Claisen Rearrangement Benzidine Rearrangement Curtius Rearrangement The reaction of Phenol with neutral FeCl 3 gives a violet color. This test is used to detect: Phenolic -OH group Alcoholic -OH group Carboxyl group Aldehyde group What is the product 'Y' in the sequence: Ethanol PCl 5 X alc.KOH Y ? Ethene Ethyne Ethyl chloride Diethyl ether Which of the following compounds is the most soluble in water? Glycerol Ethylene glycol Ethanol Propan-1-ol In the Victor Meyer test, the appearance of a blue color after the addition of NaOH indicates the presence of which type of alcohol? Secondary alcohol Primary alcohol Tertiary alcohol Phenol Which of the following compounds is formed when ethane-1,2-diol is treated with periodic acid ( HIO 4 )? Formaldehyde Acetaldehyde Glyoxal Formic acid The reaction of phenol with benzene diazonium chloride in alkaline medium to form p -hydroxyazobenzene is an example of: Electrophilic substitution Nucleophilic substitution Electrophilic addition Nucleophilic addition The boiling point of propan-1-ol is higher than that of butane because of: Intermolecular hydrogen bonding in propan-1-ol Van der Waals forces in propan-1-ol Dipole-dipole interactions in butane The higher molecular mass of propan-1-ol Which of the following compounds will give a positive test with FeCl 3 solution? p-Cresol Benzyl alcohol Ethyl alcohol Benzaldehyde Which of the following cannot be used as a reagent to convert an alcohol into an alkyl chloride? NaCl / H2O PCl5 PCl3 SOCl2 What is the correct order of the ease of dehydration of the following alcohols using concentrated H 2SO 4 ? Tertiary > Secondary > Primary Primary > Secondary > Tertiary Secondary > Tertiary > Primary Tertiary > Primary > Secondary Phenol and cyclohexanol can be best distinguished by using: Neutral FeCl 3 solution Br 2 in CCl 4 Sodium metal Lucas reagent Which of the following pairs of reagents can be used to distinguish between methanol and ethanol? Salicylic acid and concentrated H 2SO 4 Iodoform test Sodium metal Schiff's reagent The linear polymer formed by the reaction of phenol and formaldehyde in the presence of an acid catalyst is called: Novolac Bakelite Melamine Buna-S What is the product when phenol is treated with excess bromine water? 2,4,6-Tribromophenol o-Bromophenol p-Bromophenol 2,4-Dibromophenol Which of the following will exhibit the highest boiling point? CH 3CH 2CH 2CH 2OH CH 3CH 2OCH 2CH 3 CH 3CH 2CH 2CHO CH 3CH 2CH 2CH 3 The IUPAC name of the compound with the formula HO-CH 2-CH(OH)-CH 2-OH is: Propane-1,2,3-triol Glycerol 1,2,3-Trihydroxypropane Propan-1,2,3-ol When 2-methylpropan-2-ol is treated with Lucas reagent at room temperature, which of the following happens? Turbidity appears immediately Turbidity appears after 5 minutes No turbidity is observed A red color is produced Which of the following tests is used to detect the presence of the phenolic -OH group using a diazonium salt? Coupling reaction Carbylamine test Lucas test Iodoform test In the dehydration of alcohols to form alkenes, the order of reactivity is: 3 > 2 > 1 1 > 2 > 3 2 > 1 > 3 3 > 1 > 2 Which is the most suitable reagent for the following conversion: R-CH 2-OH R-CHO ? PCC (Pyridinium chlorochromate) KMnO 4/H + K 2Cr 2O 7/H + CrO 3/H 2SO 4 Which of the following enzymes is used to convert glucose into ethanol during fermentation? Zymase Invertase Maltase Diastase Which one of the following compounds is most acidic :- Cl-CH2-CH2-OH The general molecular formula, which represents the homologus series of alkanols is:- C nH 2n O 2 C nH 2n O C nH 2n+1 O C nH 2n+2 O Of the following alcohols, the one that would react fastest with conc. HCl and anhydrous ZnCl2 is 2-methylpropanol Butan-1-ol Butan-2-ol 2-methylpropan-2-ol In the reaction Dichloromethyl anion ( CHCl2 - ) Formyl cation ( CHO + ) Dichloromethyl cation ( CHCl2 + ) Dichlorocarbene ( :CCl2 ) Given below are two statements: Statement I: In Lucas test, primary, secondary and tertiary alcohols are distinguished on the basis of their reactivity with conc. HCl + ZnCl2 , known as Lucas Reagent. Statement II: Primary alcohols are most reactive and immediately produce turbidity at room temperature on reaction with Lucas Reagent. In the light of the above statements, choose the most appropriate answer from the options given below: Both Statement I and Statement II are incorrect Statement I is correct but Statement II is incorrect Statement I is incorrect but Statement II is correct Both Statement I and Statement II are correct Which one of the following alcohols reacts instantaneously with Lucas reagent? CH3-CH2-CH2-CH2OH CH3 - CH2 - CH3 | CH - OH CH3 - CH3 | CH - CH2OH The functional group that can be identified through phthalein dye test is : Carboxylic acid Alcohol Aldehyde Phenolic Which alcohol gives immediate turbidity with Lucas reagent? 2-Methylpropan-2-ol Butan-2-ol Butan-1-ol Propan-1-ol Which of the following compounds will give a yellow precipitate with I 2 and NaOH ? CH 3CH(OH)CH 2CH 3 CH 3CH 2CH 2OH CH 3CH 2CH 2CH 2OH C 6H 5CH 2OH In the reaction of phenol with Br 2 in CS 2 at low temperature, the product is: p -Bromophenol 2,4,6-Tribromophenol m -Bromophenol o-Bromophenol only Propan-1-ol and Propan-2-ol can be best distinguished by: Oxidation with KMnO 4 followed by reaction with Fehling solution Reaction with ZnCl 2/HCl Reaction with PCl 5 Reaction with LiAlH 4 Identify the compound that will react with NaOH to form a salt and with CH 3COCl to form an ester. C 6H 5OH C 2H 5OH C 6H 5OCH 3 CH 3COOH Predict the major product 'B' in the sequence: Ethanol PBr 3 A alc. KOH B . Ethene Ethyne Ethyl bromide Diethyl ether Phenol reacts with benzene diazonium chloride in a basic medium to give an orange-colored dye. The structure of this dye is: p-Hydroxyazobenzene o-Hydroxyazobenzene p-Aminoazobenzene Azobenzene The reaction of benzoyl chloride with phenol in the presence of NaOH is called: Schotten-Baumann reaction Friedel-Crafts reaction Perkin reaction Cannizzaro reaction Which test is used to distinguish between primary, secondary, and tertiary alcohols based on the color of the final product? Victor Meyer's test Lucas test Tollens' test Fehling's test Identify the major product 'P' in the following reaction: CH 3-CH=CH 2 1. B 2H 6 2. H 2O 2/OH - P . CH 3-CH 2-CH 2-OH CH 3-CH(OH)-CH 3 CH 3-CH 2-CHO CH 3-CO-CH 3 The correct increasing order of the boiling points of the following compounds is: CH 3CH 2CH 2OH (I), CH 3CH 2OCH 2CH 3 (II), CH 3CH 2CH 2CH 3 (III), CH 3CH 2CHO (IV). III < II < IV < I I < IV < II < III III < IV < II < I IV < III < II < I The functional group isomer of ethyl alcohol is: Dimethyl ether Diethyl ether Methyl ethyl ether Acetone In the reaction of phenol with phthalic anhydride in the presence of concentrated H 2SO 4 , the product formed is: Phenolphthalein Fluorescein Aspirin Salol Which of the following is the correct order of acidity for the following compounds? (I) Phenol, (II) p -Nitrophenol, (III) m -Nitrophenol, (IV) p -Cresol. II > III > I > IV II > I > III > IV III > II > I > IV I > II > III > IV What are the conditions required for the commercial production of phenol from chlorobenzene (Dow's Process)? NaOH , 623 K , 300 atm NaOH , 298 K , 1 atm Na 2CO 3 , 373 K , 10 atm HCl , 500 K , 50 atm The reaction of an alcohol with Lucas reagent ( conc. HCl + anh. ZnCl 2 ) follows which mechanism? S N1 S N2 E1 E2 The drug Paracetamol (p-acetamidophenol) is prepared by the reaction of p-aminophenol with: Acetic anhydride Acetyl chloride Methyl chloride Formic acid When phenol reacts with CCl 4 and NaOH followed by acidification, the major product is: Salicylic acid Salicylaldehyde Benzoic acid Phthalic acid Which statement correctly explains why o-nitrophenol is more steam-volatile than p-nitrophenol? o-Nitrophenol has intramolecular hydrogen bonding o-Nitrophenol has intermolecular hydrogen bonding p-Nitrophenol has intramolecular hydrogen bonding o-Nitrophenol has a higher molecular weight Anisole undergoes Friedel-Crafts acetylation with CH 3COCl in the presence of anhydrous AlCl 3 to yield: 4-Methoxyacetophenone 2-Methoxyacetophenone Both 4-Methoxyacetophenone and 2-Methoxyacetophenone Acetophenone What happens when tert-butyl alcohol is passed over heated copper at 573 K ? Dehydration to form isobutylene Dehydrogenation to form a ketone Oxidation to form an acid No reaction occurs When phenol is treated with H 2 in the presence of a Nickel catalyst at high temperature, the product is: Cyclohexanol Benzene Cyclohexane Cyclohexanone The reaction of phenol with neutral ferric chloride solution gives a characteristic color due to the formation of a complex. This color is: Violet Green Red Blue In the Victor Meyer test, a primary alcohol produces a blood-red color. This color is due to the formation of: Sodium salt of nitrolic acid Pseudonitrole Nitroalkane Nitrite ester Phenol reacts with neutral FeCl 3 to form a violet-colored complex. The formula of this complex is: [Fe(OC 6H 5) 6] 3- [Fe(C 6H 5) 6]Cl 3 Fe(OH) 3 [Fe(OC 6H 5) 3] The reaction of an alkene with peroxyformic acid ( HCOOOH ) followed by hydrolysis yields: trans-1,2-diol cis-1,2-diol Epoxide Aldehyde The reaction of phenol with NaNO 2 and concentrated H 2SO 4 followed by dilution with water and addition of NaOH produces a deep blue or violet color. This test is known as: Liebermann's nitroso reaction Reimer-Tiemann reaction Kolbe's reaction Gattermann reaction Which of the following reagents is used to convert Benzyl alcohol to Benzaldehyde specifically? MnO 2 LiAlH 4 KMnO 4/H + Zn-Hg/HCl The major product formed when phenol is treated with H 2SO 4 at 373 K ( 100 C ) is: p-phenolsulfonic acid o-phenolsulfonic acid o,p-phenoldisulfonic acid m-phenolsulfonic acid Dehydration of Butan-2-ol with concentrated H 2SO 4 at 443 K mainly yields: trans-But-2-ene But-1-ene cis-But-2-ene 2-methylpropene Identify the product formed when Ethylene glycol is treated with periodic acid ( HIO 4 ): Formaldehyde Acetaldehyde Glyoxal Formic acid The reaction of Phenol with conc. H 2SO 4 and conc. HNO 3 gives Picric acid. However, to get a better yield, phenol is first treated with: conc. H 2SO 4 dil. HNO 3 PCl 5 Br 2/CS 2 Primary, secondary and tertiary alcohols can be distinguished by the Dichromate test. A tertiary alcohol: Does not change the orange color of the solution Turns the solution green immediately Turns the solution blue Forms a carboxylic acid immediately What is the major product obtained when propene reacts with B 2H 6 followed by treatment with H 2O 2 in the presence of NaOH ? Propan-1-ol Propan-2-ol Propanal Propane-1,2-diol The reaction of phenol with p -nitrobenzenediazonium chloride in a weakly basic medium yields a dye. What is the color of this dye? Orange-red Yellow Blue Green Which of the following alcohols is the most soluble in water? n-butyl alcohol isobutyl alcohol sec-butyl alcohol tert-butyl alcohol Reaction of CH 3MgBr with CH 3CHO followed by hydrolysis gives an alcohol. This alcohol on treatment with Cu at 573 K gives: Acetone Acetaldehyde Propanal Ethyl methyl ether Which of the following compounds has the highest value of pK a ? Phenol p-Nitrophenol m-Nitrophenol o-Nitrophenol Which is the correct order of reactivity of the following toward esterification with CH 3COOH ? CH3OH > CH3CH2OH > (CH3)2CHOH > (CH3)3COH (CH3)3COH > (CH3)2CHOH > CH3CH2OH > CH3OH CH3CH2OH > CH3OH > (CH3)2CHOH > (CH3)3COH (CH3)2CHOH > CH3OH > CH3CH2OH > (CH3)3COH Which of the following represents the correct order of increasing acidic strength? Ethanol < Water < Phenol Water < Ethanol < Phenol Phenol < Water < Ethanol Ethanol < Phenol < Water Arrange the following alcohols in decreasing order of their boiling points: (I) n -Butyl alcohol, (II) iso -Butyl alcohol, (III) sec -Butyl alcohol, (IV) tert -Butyl alcohol. I > II > III > IV IV > III > II > I I > III > II > IV I > II > IV > III The formation of salicylaldehyde from phenol using HCN and HCl in the presence of AlCl 3 is known as: Gattermann reaction Gattermann-Koch reaction Reimer-Tiemann reaction Vilsmeier-Haack reaction Which of the following statements is true regarding the acidity of p -nitrophenol and p -cresol compared to phenol? p -Nitrophenol is more acidic, and p -cresol is less acidic than phenol. p -Nitrophenol is less acidic, and p -cresol is more acidic than phenol. Both are more acidic than phenol. Both are less acidic than phenol. Hydroquinone on oxidation with silver oxide ( Ag 2O ) or acidified K 2Cr 2O 7 yields: p -Benzoquinone Resorcinol Catechol Phthalic acid Which of the following reagents is most suitable for converting a primary alcohol into an aldehyde while preventing further oxidation to a carboxylic acid? Pyridinium chlorochromate (PCC) Acidified K 2Cr 2O 7 KMnO 4 in acidic medium CrO 3 in H 2SO 4 Which of the following reagents can selectively oxidize benzylic and allylic alcohols to aldehydes or ketones without affecting other isolated hydroxyl groups? MnO 2 KMnO 4 K 2Cr 2O 7 CrO 3 / H 2SO 4 Which of the following will have the highest pK a value? p -Methylphenol p -Nitrophenol m -Nitrophenol Phenol Which of the following compounds is most stable as a hydrate due to the presence of strong intramolecular hydrogen bonding? CCl 3CH(OH) 2 CH 3CH(OH) 2 CH 3COCH 3 HCHO What is the product formed when phenol is oxidized with chromic acid ( Na 2Cr 2O 7 / H 2SO 4 )? p -Benzoquinone Catechol Resorcinol Hydroquinone Identify the product formed when phenol reacts with phthalic anhydride in the presence of concentrated H 2SO 4 . Phenolphthalein Fluorescein Aspirin Salol Which of the following orders of acidic strength is correct? m-nitrophenol > phenol > p-cresol p-cresol > phenol > m-nitrophenol phenol > m-nitrophenol > p-cresol m-nitrophenol > p-cresol > phenol When 2-hydroxybenzoic acid is heated with phenol in the presence of POCl 3 , the product is: Salol Aspirin Methyl salicylate Benzoyl phenol The reagent used in the 'Gatterman reaction' (not Koch) for the synthesis of phenolic aldehydes is: HCN + HCl + AlCl 3 CO + HCl + AlCl 3 CHCl 3 + NaOH CH 3Cl + AlCl 3 The reaction of glycol with periodic acid ( HIO 4 ) leads to the cleavage of the C-C bond. What is the product if the starting material is propane-1,2-diol? HCHO and CH 3CHO 2 molecules of HCHO 2 molecules of CH 3CHO CH 3COCH 3 When glycerol is treated with concentrated HNO 3 and H 2SO 4 , the major product is: Glyceryl trinitrate Nitroglycerine Picric acid Acrolein