RBSE Class 12 Chemistry Important Questions Chapter 11 Alcohols, Phenols and Ethers

Rajasthan Board RBSE Class 12 Chemistry Important Questions Chapter 11 Alcohols, Phenols and Ethers Important Questions and Answers.

RBSE Class 12 Chemistry Chapter 11 Important Questions Alcohols, Phenols and Ethers

Objective Type Questions:

Question 1. 
Chloroethane (C₂H₅Cl) reacts with A to form diethylether. The compound A may be:
(a) NaOH
(b) H₂SO₄
(c) C₂H₅ONa
(d) Na₂S₂O₃
Answer:
(c) C₂H₅ONa

Question 2. 
Primary alcohol on catalytic hydrogenation gives a/an:
(a) aldehyde
(b) Ketone
(c) alkane
(d) ester
Answer:
(a) aldehyde

 

Question 3. 
An organic compound X having C, H and O possesses a pleasant odour with boiling point of 78°C. 
(a) C₂H₅C
(b) C₂H₅OH
(c) CH₃COOC₂H₅
(d) C₂H₆
Answer:
(b) C₂H₅OH

Question 4. 
An organic compound having molecular formula C₄H₉Cl on reaction with Na in the presence of di-ethyl ether gives a hydrocabon which on monochlorination gives only one chloroderivative, the organic compound is:
(a) n-butyl chloride 
(b) iso-butylchloride 
(c) tert-butyl chloride
(d) sec. butylchloride
Answer:
(c) tert-butyl chloride

Question 5. 
An oxygen containing organic compound forms a carboxylic acid as the main product upon oxidation with its molecular mass higher by 14 units. The organic compound is:
(a) an aldephyde
(b) a ketone
(c) a primary alcohol
(d) a secondary alcohol
Answer:
(c) a primary alcohol

Question 6. 
An alcohol is less volatile than ether having same molecular formula. It is due to:
(a) inter-molecular H-bonding in alcohol
(b) inter-molecular H-bonding in ethers 
(c) dipolar nature of ethers
(d) resonance in alcohol
Answer:
(a) inter-molecular H-bonding in alcohol

Question 7. 
Which one of the following in least acidic?
(a) Phenol
(b) p-nitrophenol
(c) p-chlorophenol
(d) o-cresol
Answer:
(d) o-cresol

Question 8. 
Which of the following alkenes produces tertbutyl alcohol on acid hyration?
(a) CH_3-CH=CH₂
(b) CH₃-CH-CH-CH₃
(c) CH₃-CH₂-CH=CH₂ 
(d) (CH₃)₂C=CH₂
Answer:
(d) (CH₃)₂C=CH₂

Question 9. 
Acid catalysed hydration of alkenes except ether leads to the formation of:
(a) Primary alcohol
(b) Secondary or tertiary alcohol
(c) Mixture of secondary and tertiary alcohol
(d) Mixture of primary and secondary alcohol
Answer:
(b) Secondary or tertiary alcohol

Question 10. 
Which of the following cannot be formed as a prod- uct in the reaction given below under any condition?
 (a) C₂H₄
 (b) C₂H₅HSO₄
(c) C₂H₅OC₂H₅
(d) C₂H₂
Answer:
(d) C₂H₂

Question 11. 
Denatured alcohol is:
(a) Ethanol + Methanol
(b) Rectified spirit
(c) Ethanol
(d) Rectified spirit + methanol + naphtha
Answer:
(d) Rectified spirit + methanol + naphtha

Question 12.
Which of the following reactions converts ethylchloride in to diethyl ether?
(a) Wurtz reactions
(b) Williamson's synthesis
(c) Grignard reagent
(d) Perkin's reaction
Answer:
(b) Williamson's synthesis

Question 13.
............reaction forms diethyl ether from ethanol.
(a) Hydrogenation
(b) Dehydration
(c) Dehydrogenation
(d) Heterolytic fission
Answer:
(b) Dehydration

Question 14. 
Which of the following alcohols would react fastest with Lucas reagent?
(a) 2-Butanol
(b) 1-Butanol 
(c) 2-Methyl propanol 
(d) 2-Methylpropan-2-ol 
Answer:
(d) 2-Methylpropan-2-ol 

Question 15. 
Which factor is more effective in the preparation of alkene from alcohol by using Al₂O₃?
(a) Temperature
(b) Concentration
(c) Surface area of Al₂O₃ 
(d) Porosity of Al₂O₃
Answer:
(a) Temperature

Very Short Answer Type Questions:

Question 1. 
Give the IUPAC name of the following compound:

Answer:

IUPAC name: 2-bromo-3-methyl-but-2-en-1-ol 

Question 2. 
Give the IUPAC name of the following compound:

Answer:

IUPAC Name: Hex-1-en-3-ol or 3-Hexenol

Question 3. 
Write the structure of the compound whose IUPAC name is 1-phenylpropan-2-ol.
Answer:

Question 4. 
How would you convert ethanol to ethene ?
Answer:

Question 5. 
Draw the structure of 2,6-Dimethylphenol.
Answer:

Question 6. 
Draw the structural formula of 2-methylpropan- 2-ol molecule.
Answer:

Question 7. 
Draw the structure of hex-1-en-3-ol compound. 
Answer:
CH₂ = CH - CH(OH) - CH₂ -CH₂ - CH₃

Question 8. 
Ortho nitrophenol has lower boiling point than p-nitrophenol. Why? 
Answer:
Ortho-nitrophenol has lower boiling point due to formation of intramolecular H-bonding whereas p- nitrophenol forms intermolecular H-bonding.

Question 9. 
Ortho-nitrophenol is more acidic than ortho methoxyphenol. Why? 
Answer:
NO₂ group is an electron withdrawing group while methoxy group is electron donating in nature. The release of H⁺ is easier from o-nitrophenol while it is difficult from o-methoxyphenol.

Question 10. 
The C-O bond is much shorter in phenol than in ethanol. Give reason. 
Answer:
Carbon of C-Obond of phenol is sp² hybridised, So it acquires a partial double bond character but in ethanol, it is sp³ hybridised and a single bond. Double bond is shorter than a single bond.

Question 11. 
Write the IUPAC name of the following:

Answer:
IUPAC name: 2-Bromo-3-methyl but-2-en-1-ol.

Question 12. 
Of the two hydroxy organic compounds ROH and R'OH the first one is basic and other is acidic in behavior. How is R different from R'? 
Answer:
When R = alkyl ROH behaves as a Bronsted base and when R'-aryl, ROH behaves as a Bronsted acid.

Question 13. 
Give a chemical test to distinguish between 2- Pentanol and 3-Pentanol. 
Answer:
2-pentanol gives lodoform test with yellow ppt of lodo form while 3-pentanol does not give this test. 

Question  14. 
Write the chemical reaction to explain Kolbe's reaction.
Answer:
The Kolbe reaction can be classified as a carboxylation chemical reaction. The reaction occurs when sodium phenoxide is allowed to absorb carbon dioxide and the resulting product is heated at a temperature of a 125-degree celsius and a pressure of over a hundred atmospheres. An unstable intermediate is now formed.

Question 15. 
How would you obtain ethane-1,2-diol from Ethanol ?
Answer:

Question 16. 
How would you obtain acetophenone from phenol? 
Answer:

Question 17. 
How would you obtain phenol from benzene?
Answer:

Question 18. 
Write IUPAC name of the following:

Answer: 
IUPAC name: 2-Methoxy-5-methyl phenol 

Question 19. 
Which of the following isomers is more volatile: o-nitrophenol or p-nitrophenol?
Answer:
o-nitrophenol is more volatile than p-nitrophenol due to intramolecular hydrogen bonding.

Question  20. 
Name the alcohol that is used to make the following ester:

Answer: 
Alcohol used: Propan-2-ol

Question  21. 
Write the IUPAC name of the given compound.

Answer: 
2,5-dinitrophenol.

Question  22. 
Write the IUPAC name of the given compound:

Answer: 
IUPAC name: 1-Ethoxy-2-methylpropane 

Question 23. 
Write the IUPAC name of the given compound:

Answer: 
2-Phenylethanol.

Question 24. 
Write equation of the nitration of anisole.
Answer:

Question  25. 
Out of CH₃OH and  which one is more acidic?
Answer:
is more acidic, as Phenoxide formed is more stabilized by Resonance.

Question  26. 
Write the IUPAC name of the following compound: 

Answer:
3-phenylprop-2-en-1-ol

Question  27. 
Write IUPAC name of the following compound:

Answer: 
2,3-Dinitrophenol.

Question  28. 
What happens when phenol is heated with zinc dust?
Answer: 
Benzene is formed when phenol is heated with zinc dust.

Question  29. 
What happens when phenol is treated with bromine water?
Answer: 
2, 4, 6-tribromophenol is formed when phenol is treated with bromine water.

Question  30. 
Give simple chemical test to distinguish between the following pair of compounds:
Benzoic acid and Phenol
Answer: 
Ferric chloride test: Add neutral FeCl₃ in both the solutions, phenol reacts with neutral FeCl₃ to form an iron-phenol complex giving violet colour but benzoic acid does not.

Short Answer type Questions:

Question 1.
Complete the following reaction equations:

Answer:

Question  2. 
Illustrate the following reactions giving a chemical equation for each: 
(i) Kolbe's reaction 
(ii) Williamson synthesis of an ether. 
Answer: 
(i) Kolbe's reaction: Phenol reacts with CO₂ in presence of sodium hydroxide (NaOH) at 4-7 atm and 390 - 410 K giving salicylic acid. 

(ii) Williamson synthesis of an ether: The reaction involves the nucleophilic substitution of the halide ion from the alkyl halide by the alkoxide ion by S₂ mechanism. 
Example: 

Question  3. 
Explain the following reactions with an example for each: 
(i) Reimer-Tiemann reaction 
(ii) Friedel-Crafts reaction. 
Answer: 
(i) Reimer-Tiemann reaction: Treatment of phenol with CHCl₃, in presence of aqueous NaOH at 340K followed by hydrolysis gives salicylaldehyde. 
Example: 

(ii) Friedel-Crafts reaction: This reaction is used for introducing an alkyl or an acyl group into an aromatic compond in presence of Lewis acid catalyst (AICl₃) 
Example: 

Question  4. 
How are the following conversions carried out? 
(i) Propene to propan-2-ol 
(ii) Ethylmagnesium chloride to propan-1-ol. 
Answer: 
(i) Propene to propan-2-ol 

(ii) Ethylmagnesium chloride to propan-1-ol 

Question  5. 
How are the following conversions carried out? 
(i) Benzyl chloride to benzyl alcohol, 
(ii) Methyl magnesium bromide to 2-methylpropan-2-ol. 
Answer: 
(i) Benzyl chloride to benzyl alcohol 

(ii) Methyl magnesium bromide to 2-methylpropan-2-ol 

Question  6. 
Explain the following giving one example for each: 
(i) Reimer-Tiemann reaction 
(ii) Friedel-Craft's acetylation of anisole. 
Answer: 
(i) Reimer-Tiemann reaction: Treatment of phenol with CHCl₃, in presence of aqueous NaOH at 340K followed by hydrolysis gives salicylaldehyde. 
Example: 

(ii) Friedel-Craft's acetylation of anisole: 

Question  7. 
How would you obtain? 
(i) Picric acid (2, 4, 6-trinitrophenol) from phenol, 
(ii) 2-Methylpropene from 2-methylpropanol? 
Answer: 
(i) Picric acid from phenol: 

(ii) 2-Methylpropene from 2-methylpropanol: 

Question  8. 
Explain the mechanism of acid catalysed hydration of an alkene to form corresponding alcohol. 
Answer: 
Acid catalyed hydration : Alkenes react with water in the presence of acid as catalyst to form alcohols. 

Mechanism: It involves three steps: 
(i) Protonation of alkene to form carbocation by electrophilic attack of H₃O⁺

(ii) Nucleophilic attack of water on carbocation 

(iii) Deprotonation to form an alcohol 

Question  9. 
Explain the following behaviours: 
(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses. 
(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol. 
Answer: 
(i) Alcohols can form H-bonds with water and break the H-bonds already existing between water molecules. So they are soluble in water. 

On the other hand, hydrocarbons cannot form H-bonds with water and hence they are insoluble in water. 

(ii) Due to strong -R and -I effect of the - NO, electron density in the -OH bond decreases and hence the loss of a proton becomes easier. Moreover o-nitrophenoxide ion is stabilized by resonance, there by making o-nitrophenol a stronger acid. In o-methoxyphenol, due to + Reffect of the - OCH, group the electron density in the O-H bond increases thereby making the loss of proton difficult. Further more, the o-methoxy phenoxide ion left after the loss of a proton is destabilized by resonance because the two negative charges repel each other. So o-methoxyphenol is a weaker acid. 

Question  10. 
Explain the mechanism of the following reaction: 

Answer: 

Mechanism: Step 1: Protonation of alcohol 

Step 2: Nucleophillic attack by unprotonated alcohol molecule an protonated alcohol molecule 

Step 3: Loss of a porton to form ethoxy ethane 

Question  11. 
How will you convert? 
(i) Propene to propan-2-ol? 
(ii) Phenol to 2, 4, 6-trinitrophenol 
Answer: 
(i) Propene to propan-2-ol 

(ii) Phenol to 2, 4, 6-trinitrophenol 

Question  12. 
How will you convert the following? 
(i) Propan 2-ol to propanone 
(ii) Phenol to 2, 4, 6-tribromophenol 
Answer: 
(i) Propan-2-ol to propanone 

(ii) Phenol to 2, 4, 6-tribromophenol : Phenol reacts with bromine in presence of polar solvent H₂O to form 2, 4, 6- tribromophenol (white ppt.) 

Question  13. 
How will you convert? 
(i) Propene to Propan-1-ol 
(ii) Ethanal to Propan-2-ol? 
Answer: 
(i) Propene to Propan-1-ol 

(ii) Ethanal to Propan-2-ol 

Question 14. 
How are the following conversion carried out? 
(i) Propene to Propan-2-ol 
(ii) Ethyl chloride to Ethanal 
Answer: 
(i)Propene to Propan-2-ol 

(ii) Ethyl chloride to Ethanal 

Question  15. 
Write the mechanism of acid dehydration of ethanol to yield ethene. 
Answer: 
The mechianism of dehydration of ethanol involves the following steps: 
Step 1: Formation of protonated alcohol 

Step 2: Formation of Carbocation: It is the slowest and rate determining step. 

Step 3: Formation of ethene by elimination of a proton 

 
Question  16. 
Write the mechanism of the following reaction.

Answer: 
Mechanism: 
Step 1: 

Step 2: 

Step 3: 

Question  17. 
(a) Arrange the following compounds in the increasing order of their acid strength : 
p-cresol, p-nitrophenol, phenol 
(b) Write the mechanism (using curved arrow notation) of the following reaction: 

Answer: 
(i) Order of acidic strength: 
p-cresol <phenol <p-nitrophenol 

(b) Mechanism of acid catalysed hydration of alkene: 
Step 1: Protonation of alkene to form carbocation by electrophilic attack of H₂O⁺. 

Step 2: Nucleophilic attack of water on carbocation 

Step 3: Deprotonation to form an alcohol 

Question  18. 
Write the structures of the product when Butan 2-ol reacts with the following: 
(a) CrO₃
(b) SOCl₂
Answer: 

Question  19. 
Explain the mechanism of the following reactions : 
(i) Addition of Grignard's reagent to the carbonyl group of a compound forming an adduct followed by hydrolysis. 
(ii) Acid catalysed dehydration of an alcohol forming an alkene. 
(iii) Acid catalysed hydration of an alkene forming an alcohol. 
Answer: 
(i) Carbonyl group undergoes nucleophilic addition reaction with Grignard reagent to form an adduct which undergoes hydrolysis to give alcohol in the following manner: 

(ii) The mechanism of dehydration of ethanol involves the following steps: 
Mechanism: It involves the following three step: 
Step 1: Formation of protonated alcohol 

Step 2: Formation of Carbocation: It is the slowest and rate determining step. 

Step 3: Formation of ethene by elimination of a proton 

(iii) Acid catalysed hydration : Alkenes react with water in the presence of acid as catalyst to form alcohols. Mechanism: It involves the following three steps: 
Step 1: Protonation of alkene to from carbocation by electrophilic attack of H₃O⁺

Step 2: Nucleophilic attack of water on carbocation 

Step 3: Deprotonation to from an alcohol

Question  20. 
Explain the following observations: 
(i) The boiling point of ethanol is higher than that of methoxymethane. 
(ii) Phenol is more acidic than ethanol. 
(iii) o- and p-nitrophenol are more acidic than phenol. 
Answer: 
(i) Due to presence of intermolecular H-bonding, associated molecules are formed, hence ethanol has high boiling point while methoxymethane does not have intermolecular H-bonding. 

(ii) Phenol on losing H⁺ ion forms phenoxide ion, and ethanol on losing H⁺ ion forms ethoxide ion. Phenoxide ion is more stable than ethoxide ion as phenoxide ion exists in resonance structure. Due to this, phenol is more acidic than ethanol. 

(iii) Both o- and p-nitrophenol contain the NO₂ group which is an electron withdrawing group. Due to -R and -I effect of the -NO₂ group, electron density in the OH bond of substituted phenol decreases and hence the loss of proton becomes any and therefore more acidic. 

Question  21. 
How would you convert the following? 
(i) Phenol to benzoquinone 
(ii) Propanone to 2-methylpropan-2-ol 
(iii) Propene to propan-2-ol 
Answer: 
(i) Phenol to benzoquinone 

(ii) Propanone to 2-methylpropan-2-ol 

(iii) Propene to propan-2-ol 

Question  22. 
How would you obtain the following 
(i) Benzoquinone from phenol 
(ii) 2-Methylpropan-2-ol from ethylmagnesium chloride 
(iii) Propan-2-ol from propene 
Answer: 
(i) Benzoquinone form phenol 

(ii) Benzyl chloride to benzyl alcohol 

(iii) Propene to propan-2-ol 

Question  23. 
Draw the structure and name the product formed if the following alcohols are oxidized. Assume that an excess of the oxidizing agent is used: 
(i) CH₃CH₂CH₂CH₂OH 
(iii) 2-methyl-1-propanol 
Answer: 

Structure of Product	Name of Product
(i) CH3CH2CH2COOH	Butanoic acid
(ii) CH3-CH=CH-COOH	But-2-en-1-oic acid or 2-butenoic acid
(iii) CH3-CH(CH3)-COOH	2-methylpropanoic acid

Question  24. 
(a) Illustrate the following name reactions: 
(i) Reimer-Tiemann Reaction 
(ii) Williamson Synthenis. 
(b) Give a chemical test to distinguish between 2-propanol and 2-methy1-2-propanol. 
Answer: 
(a) (i) Reimer-Tiemann reaction: Treatment of phenol with CHCl₃, in presence of aqueous NaOH at 340K followed by hydrolysis gives salicylaldehyde. 
Example: 

(ii) Williamson synthesis of an ether: The reaction involves the nucleophilic substitution of the halide ion from the alkyl halide by the alkoxide ion by S₂ mechanism. 
Example: 

(b) 2-Propanol is a secondary alcohol. When it reacts with I, in NaOH, it forms a yellow ppt of iodoform but 2 methyl- 2 propanol does not respond to this test. 

Question  25. 
(a) Give a separate chemical test to distinguish between the following pairs of compounds: 
(i) Ethanol and Phenol 
(ii) 2-Pentanol and 3-Pentanol 
(b) Explain Kolbe's reaction with the help of suitable example. 
Answer: 
(a) (i) Ethanol on reacting with I₂ in NaOH gives yellow ppt of iodoform whereas phenol does not respond to this test. 
(ii) 2-Pentanol on reacting with I₂ in NaOH gives yellow ppt of iodoform whereas 3-pentanol does not respond to this test. 
(b) Kolbe's reaction: Phenol reacts with NaOH to give sodium phenoxide which on reaction with CO₂ in acid gives salicylic acid. 

Question  26. 
(a) How would you obtain the following 
(i) 2-methylpentan-2-ol from 2-methyl-1-pentene 
(ii) Acetophenone from phenol 
(b) Write IUPAC name of the following: 

Answer:
(a) (i) 2-Methylpentan-2-ol from 2-methyl-1-pentene 

(ii) Acetophenone from phenol 

(b) IUPAC name: 1-ethoxy-2-nitrocyclohexane. 

Question  27. 
(a) Give mechanism of preparation of ethoxy ethane from ethanol. 
(b) How is toluene obtained from phenol? 
Answer: 
(a) Mechanism of formation of ethoxy ethane 
Step 1: Protonation of ethanol 

Step 2: Nucleophillic attack by unprotonated alcohol molecule on protonated alcohol molecule 

Step 3: Loss of proton to form ethoxy ethane 

(b) Toluene from Phenol 

Question  28. 
(a) Give chemical tests to distinguish between the following pairs of compounds: 
(i) Pentan-2-ol and Pentan-3-ol 
(ii) Methanol and Phenol 
(b) o-nitro phenol is more acidic than o-methoxy phenol. Explain why. 
Answer: 
(a) (i) 2-pentanol gives iodoform test with yellow ppt of iodoform while 3-pentanol does not give this test. 
(ii) Distinction between Methanol and Phenol: 
By FeCl₃ test: Phenol gives violet coloured solution with FeCl₃ while methanol dose not. 

(b) o-nitrophenol is more acidic than o-methoxy phenol due to presence of NO₂ group which has-I effect. It weakens the O-H bond of phenol by withdrawing their electrons and thus releases H⁺ ion easily while due to +I, + R effect of OCH₃, o-methoxy phenol is less acidic. 

Question  29. 
(a) Write the mechanism of the following reaction: 

(b) Write the equation involved in Reimer-Tiemann reaction. 
Answer: 

Mechanism: SN² mechanism 

(b) (i) Reimer-Tiemann reaction: Treatment of phenol with CHCl₃, in presence of aqueous NaOH at 340K followed by hydrolysis gives salicylaldehyde. 
Example: 

Question  30. 
How do you convert the following: 
(i) Phenol to anisole 
(ii) Propan-2-ol to 2-methylpropan-2-ol 
(iii) Aniline to phenol. 
Answer: 

Question  31. 
(a) Write the mechanism of the following reaction: 

(b) Write the equation involved in the acetylation of Salicylic acid. 
Answer: 


Question 32. 
Give reasons for the following: 
(i) Phenol is more acidic than methanol. 
(ii) The C-Q-H bond angle in alcoholsin slightly less than the tetrahedral angle (190°28′). 
(iii) (CH₃)₃C-O-CH₃ on reaction with HI gives (CH₃)₃CI and CH₃ - OH as the main products and not (CH₃)₃C - OH and CH₃ - I. 
Answer: 
(i) Phenol is more acidic than methanol because in phenol, phenoxide ion formed is more stabilized by resonance than phenol. There is no resonance in methanol. 
(ii) The C-O-H bond angle in alcohol is slightly less than tetrahedral angle due to repulsion between the ion pairs of electrons of oxygen. 
(iii) (CH₃)₃C* is 3° carbocation which is more stable than CH₃⁺ for SN¹ reaction. 

Question  33. 
How are the following conversions carried out? 
(i) Propene to propan-2-ol 
(ii) Benzly chloride to Benzyl alcohol 
(iii) Anisole to p-Bromoanisole. 
Answer: 
(i) Propene to propan-2-ol 


(ii) Benzyl chloride to Benzyl alcohol 

(iii) Anisole to p-Bromoanisole. 

 
Question  34. 
Write the major product in the following equations: 

(iii) CH₃ - Cl + CH₃CH₂ -ONa → ?
Answer: 

Question  35. 
Write the main product(s) in each of the following reaction. 

Answer: 

Question  36. 
Write the final product(s) in each of the following reaction: 

Answer: 

Question  37. 
(a) What happens when CH₃-O-CH₃ is heated with HI? 
(b) Explain mechanism for hydration of acid catalyzed ethane: 

Answer: 
(a) Methly iodide (CH₃I) and Methonal (CH₃OH) are formed when CH₃-O-CH₃ is heated with HI. 

(b) Acid catalyzed hydration: Alkenes react with water in the presence of acid as catalyst to form alcohols. Mechanism: It involves the following three steps: 
Step 1: Protonation of alkene to form carbocation by electrophilic attack of H₃O⁺. 

Step 2: Nucleophilic attack of water on carbonation 

Step 3: Deprotonation to form an alcohol 

Question  38. 
(a) Why phenol is more acidic than ethanol? 
(b) Write the mechanism of acid dehydration of ethanol to yield ether: 

Answer: 
(a) Phenol on losing H⁺ ion forms phenoxide ion, and ethanol on losing H⁺ ion forms ethoxide ion. Phenoxide ion is more stable than ethoxide ion as phenoxide ion exists in resonance structure. Due to this phenol is more acidic than ethanol. 

Long Answer Type Questions:
 
Question  1. 
(a) Write the product(s) in the following reactions : 

(b) Give simple chemical tests to distinguish between the following pairs of compounds: 
(i) Ethanol and Phenol 
(ii) Propanol and 2-methylpropan-2-ol. 
Answer: 

(b) (i) Ethanol gives a positive lodoform test. 

Phenol gives a negative lodoform test. 
 
(ii) Distinction between propanol and 2-methylpropan-2-ol: 

Question  2. 
(a) Write the formula of reagents used in the following reactions: 
(i) Bromination of phenol to 2,4,6-tribromophenol 
(ii) Hydroboration of propene and then oxidation to propanol. 
(b) Arrange the following compounds in the increasing order of their property indicated 
(i) p-nitrophenol, ethanol, phenol (acidic character) 
(ii) Propanol, Propane, Propanal (boiling point) 
(c) Write the mechanism (using curved arrow notation) of the following reaction: 

Answer:

Competition Corner:

Question 1. 
The major organic product in the reaction. imm product is:
(a) ICH₂OCH(CH₃)₂
(b) CH₃OC(CH₃)₂
(c) CH₃I + (CH₃)₂ CHOH 
(d) CH₃OH + (CH₃)₂ CHI
Answer:
(c) CH₃I + (CH₃)₂ CHOH 

Question 2. 
In the reaction:

product is:

Answer:

Question 3. 
Consider the following reaction:

The product Z is:
(a) CH₃CH₂OCH₂CH₃
(b) CH₃CH₂O-SO₃H
(c) CH₃CH₂OH 
(d) CH₂ = CH₂
Answer:
(c) CH₃CH₂OH 

Question 4. 
Consider the following reaction:

The product Z is:
(a) Benzaldehyde 
(b) Benzoic acid 
(c) Benzene
(d) Toluene
Answer:
(b) Benzoic acid 

Question 5. 
Which one of the following compounds has the most acidic nature?

Answer:

Question 6. 
Given are cyclohexanol (I), acetic acid (II), 2, 4, 6-trinitrophenol (III) and phenol (IV). In these compounds, the decreasing acidic character will be:
(a) II > III > IV > I
(b) III > IV > II > I
(c) III > II > IV > I
(d) III > II > I > IV
Answer:
(d) III > II > I > IV

Question 7. 
In the following reactions:

The major product (A) and (C) are respectively:

Answer:

Question 8. 
Which one of the following is most reactive towards electrophilic reagent?

Answer:

Question 9. 
Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI?

Answer:

Question 10. 
Among the following sets of reactants which one produces anisole?
(a) CH₃CHO; RMgX
(b) C₆H₅OH; NaOH; CH₂I
(c) C₆H₅OH; neutral FeCl₃ 
(d) C₆H₅CH₃; CH₃COCI; AlCl₃
Answer:
(b) C₆H₅OH; NaOH; CH₂I

Question 11. 
Identify Z in the sequence of reactions

(a) CH₃-(CH₂)₃-O-CH₂CH₃
(b) (CH₃)₂CH-O-CH₂CH₃
(c) CH₃(CH₂)₄-O-CH₃
(d) CH₃CH₂-CH(CH₃)-O-CH₂CH₃
Answer:
(a) CH₃-(CH₂)₃-O-CH₂CH₃

Question 12. 
The major product formed when 3, 3-dimethyl- butan-2-ol is heated with concentrated sulphuric acid is:
(a) 2,3-dimethyl-2-butene
(b) 2,3-dimethyl-1-butene
(c) 3,3-dimethyl-1-butene
(d) cis- and trans-isomers of 2,3-dimethyl-1-butene 
(e) cis- and trans-isomers of 3,3-dimethyl-2-butene 
Answer:
(a) 2,3-dimethyl-2-butene

Question 13. 
Which among the following compounds will give a secondary alcohol on reacting with Grignard reagent followed by acid hydrolysis?
I. HCHO
III. CH₃COCH₃
II.CH,CHO
IV. HCOOC₂H₅
Select the correct answer giving the order given be-low:
(a) II only
(b) III only
(c) I and V
(d) II and III
(e) II and IV
Answer:
(e) II and IV

Question 14. 
Which of the following is an appropriate set of reac- tants for preparation of 1-methoxy-4-nitrobenzene?

(a) (A)
(b) (B)
(c) Both (A) and (B)
(d) None of these
Answer:
(b) (B)

Question 15. 
Which of the following alcohols gives the best yield of dialkyl ether on being heated with a trace of sulphuric acid?
(a) 2-Pentanol
(b) Cyclopentanol
(c) 2-Methyl-2-butanol 
(d) 2-Propanol
(e) 1-Pentanol
Answer:
(e) 1-Pentanol