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Page No 154:

Question 1:

Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields.

(i) o-Cresol
(ii) m-Cresol
(iii) 2, 4-Dihydroxytoluene
(iv) Benzyl alcohol

Answer:

Monochlorination of toluene in the presence of sunlight yields benzyl chloride. On hydrolysis of benzyl chloride mucleophilic substitution reaction takes place and benzyl alcohol is obtained as the final product.

Hence, the correct answer is option (iv)

Page No 154:

Question 2:

How many alcohols with molecular formula C4H10O are chiral in nature?

(i) 1
(ii) 2
(iii) 3
(iv) 4

Answer:

The structural isomers of butanol (C4H10O) are as follows:
 
 
 
So, among the isomers of  butanol, only one isomer is chiral i.e., Butam-2-ol.

Hence, the correct answer is option (i).

Page No 154:

Question 3:

What is the correct order of reactivity of alcohols in the following reaction?

R—OH + HCl ZnCl2 R—Cl + H2O

(i) 1° > 2° > 3°
(ii) 1° < 2° > 3°
(iii) 3° > 2° > 1°
(iv) 3° > 1° > 2°

Answer:

The given nucleophilic substitution reaction takes through the formation of a intermediate carbocation and among the carbocations tertiary carbocation (3º) is most stable followed by secondary (2º) and primary (1º) respectively. The higher the stability of carbocation higher will be the reactivity of reactant molecule. Therefore, the order of reactivity of alcohol for the given reaction is 3º > 2º> 1º.

Hence, the correct answer is option (iii).

Page No 154:

Question 4:

CH3CH2OH can be converted into CH3CHO by ______________.

(i) catalytic hydrogenation
(ii) treatment with LiAlH4
(iii) treatment with pyridinium chlorochromate
(iv) treatment with KMnO4

Answer:

Partial oxidation of alcohol to obtain aldehyde is done in the presence pyridinium chlorochromate (PCC).


Hence, the correct answer is option (iii).
 



Page No 155:

Question 5:

The process of converting alkyl halides into alcohols involves_____________.

(i) addition reaction
(ii) substitution reaction
(iii) dehydrohalogenation reaction
(iv) rearrangement reaction

Answer:

The conversion of alkyl halide to alcohol is an example of substitution reaction. In this reaction, the halide group of the alkyl halide is replaced by – OH

Hence, the correct answer is option (ii).

Page No 155:

Question 6:

Which of the following compounds is aromatic alcohol?
                        
(i) A, B, C, D
(ii) A, D
(iii) B, C
(iv) A

Answer:

Phenol is also knowns as carbolic acid and is not considered as aromatic alcohol. Also, any alcohol in which the hydroxyl group is attached to a carbon which itself is bonded to an aromatic ring is regarded as aromatic in nature. Therefore, benzyl alcohol and its derivatives are aromatic in nature. Thus, compounds (B) and (C) are aromatic in nature. 

Hence, the correct answer is option (iii).

Page No 155:

Question 7:

Give IUPAC name of the compound given below.


(i) 2-Chloro-5-hydroxyhexane
(ii) 2-Hydroxy-5-chlorohexane
(iii) 5-Chlorohexan-2-ol
(iv) 2-Chlorohexan-5-ol

Answer:


The IUPAC name of the given compound is 5-chlorohexan-2-ol.

Hence, the correct answer is option (iii).

Page No 155:

Question 8:

IUPAC name of m-cresol is ___________.

(i) 3-methylphenol
(ii) 3-chlorophenol
(iii) 3-methoxyphenol
(iv) benzene-1,3-diol

Answer:

The structure of m-cresol is as follows:

IUPAC Name: 3-Methylphenol
Hence, the correct answer is option (i)

Page No 155:

Question 9:

IUPAC name of the compound ______________.

(i) 1-methoxy-1-methylethane
(ii) 2-methoxy-2-methylethane
(iii) 2-methoxypropane
(iv) isopropylmethyl ether

Answer:


The IUPAC name of the given compound is 2-Methoxypropane
Hence, the correct answer is option (iii)



Page No 156:

Question 10:

Which of the following species can act as the strongest base?
(i)   ΘOH
(ii)   ΘOR
(iii)   ΘOC6H5
 (iv)

Answer:

The conjugate base for a weak acid is quite strong. Amongst the given options, ROH is the weakest acid, therefore its conjugate base RO the strongest base.

Hence, the correct answer is option (ii).

Page No 156:

Question 11:

Which of the following compounds will react with sodium hydroxide solution in water?

(i) C6H5OH
(ii) C6H5CH2OH
(iii) (CH3)3COH
(iv) C2H5OH

Answer:

Phenol due to its acidic nature reacts readily with sodium hydroxide solution in water to give sodium phenoxide ion 

Hence, the correct answer is option (i)

Page No 156:

Question 12:

Phenol is less acidic than ______________.

(i) ethanol
(ii) o-nitrophenol
(iii) o-methylphenol
(iv) o-methoxyphenol

Answer:

The presence of electron withdrawing group at ortho or para position increases the acidic strength of phenol. Therefore, o-nitrophenol is more acidic than phenol, due to the presence of electron withdrawing nitro-group (–NO2) at ortho position.

Hence, the correct answer is option (ii).

Page No 156:

Question 13:

Which of the following is most acidic?

(i) Benzyl alcohol
(ii) Cyclohexanol
(iii) Phenol
(iv) m-Chlorophenol

Answer:

Due to the higher electronegativity of sp2 hybridised carbon of phenol to which –OH is attached, electron density decreases on oxygen. This increases the polarity of O–H bond and results in an increase in ionisation of phenols than that of alcohols. The acidity of phenol is more than the alcohols due to delocalisation of electrons over the benzene ring.  Also, the presence of an electron withdrawing group such as –Cl contributes in increasing the acidity of phenol. Therefore, m-chlorophenol is most acidic amongst the given options.

Hence, the correct answer is option (iv).

Page No 156:

Question 14:

Mark the correct order of decreasing acid strength of the following compounds.
                
(i) e > d > b > a > c
(ii) b > d > a > c > e
(iii) d > e > c > b > a
(iv) e > d > c > b > a

Answer:

The presence of electron withdrawing group like –NOon phenol increases the acidic strength of phenol whereas the presence of electron donating group like –OCH3 decreases the acidic strength of phenol. The presence of electron withdrawing group has a more pronounced effect, if present at ortho and para position. Therefore, the correct order of decreasing acidic strength is as follows:
(b) > (d) > (a) > (c) > (e)

Hence, the correct answer is option (ii).



Page No 157:

Question 15:

Mark the correct increasing order of reactivity of the following compounds with HBr/HCl.

                  
(i) a < b < c
(ii) b < a < c
(iii) b < c < a
(iv) c < b < a

Answer:

The substitution reaction of alcohol with HBr/HCl takes place through the formation of carbocation. Higher the stability of carbocation, the more favourable is the reaction. Also, the presence of an electron withdrawing group contributes in decreasing the reactivity of the alcohol for the substitution. Since –NO2 group is stronger electron withdrawing group than –Cl, therefore, the stability of carbocation increases in the order as follows:
(b) < (c) < (a)

Hence, the correct answer is option (iii).

Page No 157:

Question 16:

Arrange the following compounds in increasing order of boiling point. Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol

(i) Propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol
(ii) Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(iii) Pentan-1-ol, butan-2-ol, butan-1-ol, propan-1-ol
(iv) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-1-ol

Answer:

Boiling point increases with increase with increase in the molecular mass of alcohol. It also decreases with branching due to the decrease in surface area on branching. Therefore, the correct order of increasing boiling points for the given alcohols is as follows:
Propan-1-ol < Butan-2-ol < Butan-1-ol < Pentan-1-ol

Hence, the correct answer is option (i).

Page No 157:

Question 17:

In the given question two or more options may be correct.

Which of the following are used to convert RCHO into RCH2OH?

(i) H2/Pd
(ii) LiAlH4
(iii) NaBH4
(iv) Reaction with RMgX followed by hydrolysis

Answer:

Aldehydes can be converted into alcohol through reduction reaction. The reduction can be carried out by adding hydrogen in the presence of a catalysts like Pd, Pt or Ni or by using a reducing agent like NaBH4 or LiAlH4.

Hence, the correct answers are options (i), (ii) and (iii).

Page No 157:

Question 18:

In the given question two or more options may be correct.
Which of the following reactions will yield phenol?







 

Answer:

The reactions which would yield phenol as a product are as follows:






Hence, the correct answers are options (i), (ii) and (iii).



Page No 158:

Question 19:

In the given question two or more options may be correct.

Which of the following reagents can be used to oxidise primary alcohols to aldehydes?

(i) CrO3 in anhydrous medium.
(ii) KMnO4 in acidic medium.
(iii) Pyridinium chlorochromate.
(iv) Heat in the presence of Cu at 573K.

Answer:

The reagents that would oxidise primary alcohols to aldehydes are as follows:
(i) CrO3 in anhydrous medium

(ii) Pyridinium chlorochromate

(iii) Heat in the presence of Cu at 573 K

Hence, the correct answers are options (i), (iii) and (iv).

Page No 158:

Question 20:

In the given question two or more options may be correct.

Phenol can be distinguished from ethanol by the reactions with _________.

(i) Br2/water
(ii) Na
(iii) Neutral FeCl3
(iv) All the above

Answer:

Phenol on reaction with neutral FeCl3 gives violet color due to formation of a complex.
3Ar-OH + FeCl3(neutral) (Ar-O)3-Fe + 3HCl
It also reacts with bromine water form a white precipitate of tribromo derivative of phenol.

Ethanol does not give these tests.

Hence, the correct answers are options (i) and (iii).

Page No 158:

Question 21:

In the given question two or more options may be correct.
Which of the following are benzylic alcohols?



Answer:

For an alcohol to be benzylic alcohol, the −OH group is attached to sp3 hybridised carbon atom next to an aromatic ring. Amongst the given compounds, compounds (ii) and (iii) have –OH group attached. to sp3 hybridised carbon atom next to aromatic ring. Therefore, they are benzylic alcohols.

Hence, the correct answers are options (ii) and (iii). 

Page No 158:

Question 22:

What is the structure and IUPAC name of glycerol?

Answer:

The structure and IUPAC name of glycerol are as follows:

IUPAC name: Propane-1, 2, 3-triol



Page No 159:

Question 23:

Write the IUPAC name of the following compounds.
(a)              (b)

Answer:

(A)
 
3-Ethyl-5-methylhexan-2, 4-diol

(B)
 

Page No 159:

Question 24:

Write the IUPAC name of the compound given below.

Answer:

The IUPAC name of the compound is given below.

Page No 159:

Question 25:

Name the factors responsible for the solubility of alcohols in water.

Answer:

Alcohol forms hydrogen bonds with the molecules which contributes to the solubility of alcohols in water. The solubility of alcohol decreases with the increases in the size of alkyl, aryl group attached to the main chain.

Page No 159:

Question 26:

What is denatured alcohol?

Answer:

Commercially used alcohol is made unfit for drinking by mixing some methanol to it. This is called denaturation of alcohol and the alcohol obtained is called denatured alcohol.

Page No 159:

Question 27:

Suggest a reagent for the following conversion.

Answer:

PCC (pyridinium chlorochromate) is a complex of chromium trioxide with pyridine and HCl. It is a good reagent used to convert primary alcohols to aldehydes.

Page No 159:

Question 28:

Out of 2-chloroethanol and ethanol which is more acidic and why?

Answer:

The acidic character of alcohols is due to the polar nature of O–H bond. Chlorine atom is an electron withdrawing group which increases the polarity of O–H bond. Thus, 2-Chloroethanol is more acidic than ethanol due to −I effect of chlorine atom.

Page No 159:

Question 29:

Suggest a reagent for conversion of ethanol to ethanal.

Answer:

PCC (pyridinium chlorochromate) can be used as a reagent to convert to ethanol to ethanal
CH3CH2OHEthanol PCC CH3CHOEthanal

Page No 159:

Question 30:

Suggest a reagent for conversion of ethanol to ethanoic acid.

Answer:

Ethanol can be converted to ethanoic acid using a strong oxidising agent like acidified K2Cr2O7 or KMnO4.
CH3CH2OHEthanol K2Cr2O7/H2SO4KMnO4/H2SO4 CH3COOHEthanoic acid

Page No 159:

Question 31:

Out of o-nitrophenol and p-nitrophenol, which is more volatile? Explain.

Answer:

Ortho-nitrophenol is more volatile due to intra-molecular hydrogen bonding than para-nitrophenol as in p-nitrophenol, inter-molecular hydrogen bonding exists.

Page No 159:

Question 32:

Out of o-nitrophenol and o-cresol which is more acidic?

Answer:

The acidity of alcohol is due to polar nature of O — H bond. Higher the polarity of O — H bond, more will be the acidity.
o-Nitrophenol is more acidic than o-cresol due to –I and –R of nitro group that contributes in decreasing the electron density on oxygen tending to increase the polarity of O — H bond and leads to the effective delocalisation of negative charge in phenoxide ion.

On the other hand, methyl group in o-cresol shows +I and +R effect increases electron density on oxygen tending to decrease the polarity of O — H bond and do not favour the formation of phenoxide ion. Thus, o-cresol is less acidic than o-nitrophenol.

Page No 159:

Question 33:

When phenol is treated with bromine water, white precipitate is obtained. Give the structure and the name of the compound formed.

Answer:

The reaction that takes place when phenol is treated with bromine water is as follows:

Page No 159:

Question 34:

Arrange the following compounds in increasing order of acidity and give a suitable explanation.

Phenol, o-nitrophenol, o-cresol

Answer:

The presence of electron donating alkyl group in o-cresol intensifies the charge on phenoxide ion and reduces the stability of o-cresol as compared to phenol. On the other hand, the presence of electron withdrawing nitro group (–NO2) disperses the negative charge and stabilizes the phenoxide ion. As a result, o-nitrophenol is more acidic than phenol. Hence, increasing order of acidity is a follows:
o-Cresol < Phenol < o-Nitrophenol

Page No 159:

Question 35:

Alcohols react with active metals e.g. Na, K etc. to give corresponding alkoxides. Write down the decreasing order of reactivity of sodium metal towards primary, secondary and tertiary alcohols.

Answer:

Alcohol reacts with active metals like Na, K etc. to form corresponding alkoxides. The reaction is as follows:

The order of reactivity of alcohol towards the active metals is as follows:
Primary > Secondary > Tertiary
This can be explained on the basis of cleavage of O – H bond in alcohol. The presence alkyl group contributes in increasing the electron density around the oxygen atom of O – H bond due to +I effects shown by alkyl groups. As a result, the O – H bond is hard to cleave. Therefore, greater the number of alkyl group present, lesser will be reactivity of alcohol.

Page No 159:

Question 36:

What happens when benzene diazonium chloride is heated with water?

Answer:

Phenol is obtained as a product on heating benzene diazonium chloride with water.

Page No 159:

Question 37:

Arrange the following compounds in decreasing order of acidity.

H2O, ROH, HC ≡ CH

Answer:

A stronger acid has the ability to displace a weaker acid from its salt.
On treating RONa+ with H2O, it gives ROH. Hence, water is a stronger acid than ROH.
    HOH +  RO-Na+  NaOH  +  ROHStronger acid                                     Weaker acid              
Also, on treating sodium ethynide (CH≡CNa+) with water and alcohol, acetylene (CH≡CH) is obtained as a product.
    HOH +  HCC-Na+  NaOH  +  HCCHStronger acid                                     Weaker acid              
    ROH +  HCC-Na+  NaOR  +  HCCHStronger acid                                     Weaker acid              
So, acetylene (CH≡CH) is least acidic.
Therefore, the deceasing order of acidity of the given compounds is .

Page No 159:

Question 38:

Name the enzymes and write the reactions involved in the preparation of ethanol from sucrose by fermentation.

Answer:

Invertase enzyme is used in the conversion of sucrose to glucose and fructose.
C12H22O11Sucrose + H2O  Invertase C6H12O6Glucose + C6H12O6Fructose
Glucose and fructose undergo fermentation in the presence of zymase enzyme, which is present in yeast.
C6H12O6  Zymase 2C2H5OH + Ethanol2CO2

Page No 159:

Question 39:

How can propan-2-one be converted into tert- butyl alcohol?

Answer:

The conversion of propan-2-one to tert-butyl is shown below.

Page No 159:

Question 40:

Write the structures of the isomers of alcohols with molecular formula C4H10O. Which of these exhibits optical activity?

Answer:

The isomeric structures of alcohol with molecular formula C4H10O are as follows
 
 
 
The compound consisting of Chiral carbon are usually optically active compounds. Hence, from the isomers of C4H10O, only Butan-2-ol is optically active.



Page No 160:

Question 41:

Explain why is –OH group in phenols more strongly held as compared to –OH group in alcohols.

Answer:

In the structure of phenol, the lone pairs of electron of oxygen atoms of –OH group are in resonance with the π-electrons of the benzene ring as shown below.

As depicted from the resonating structures, in structure II, III and IV, bond between carbon and oxygen acquires partial double bond character due to resonance. But in alcohols, carbon-oxygen bond is purely single bond.
Therefore, the –OH group in phenol is more strongly held as compared to –OH group in alcohol.

Page No 160:

Question 42:

Explain why nucleophilic substitution reactions are not very common in phenols.

Answer:

Due to resonance and dispersal of negative charge over the benzene ring in phenols, the nucleophile is repelled from attacking the electron rich ortho and para positions. As a result, phenols do not give nucleophilic substitution reactions.

Page No 160:

Question 43:

Preparation of alcohols from alkenes involves the electrophilic attack on alkene carbon atom. Explain its mechanism.

Answer:

The mechanism of preparation of alcohols from alkenes is as follows:

Step 1 − Protonation of alkene by electrophilic attack of H­3O+ to form carbocation

Step 2 − Nucleophilic attack of water on the carbocation

Step 3 − Deprotonation to form alcohol

Page No 160:

Question 44:

Explain why is O=C==O nonpolar while R—O—R is polar.

Answer:

The dipole moment is CO2 is zero due to its linear geometry, the polarities of two C=O bonds get cancelled and the molecular is non-polar.

The structure of ether is similar to water and has bent structure. Thus, the polarity of two R – O groups does not get cancelled. Hence, the molecule is polar.

Page No 160:

Question 45:

Why is the reactivity of all the three classes of alcohols with conc. HCl and ZnCl2 (Lucas reagent) different?

Answer:

The reaction of alcohol with Lucas reagent (Conc. HCl and ZnCl2) proceeds through the formation of carbocation intermediate.
The stability of carbocation intermediate determines the rate of the reaction, i.e., more stable the intermediate carbocation, more reactive is the alcohol.
Tertiary carbocation being most stable among three class of carbocations are found to be most reactive towards the Lucas reagent.
Thus, the order of reactivity of three classes of alcohols is 3° > 2° > 1°.

Page No 160:

Question 46:

Write steps to carry out the conversion of phenol to aspirin.

Answer:

The reactions for conversion of phenol to aspirin are as follows:

Page No 160:

Question 47:

Nitration is an example of aromatic electrophilic substitution and its rate depends upon the group already present in the benzene ring. Out of benzene and phenol, which one is more easily nitrated and why?

Answer:

Nitration of phenol is easy as compared to benzene because the presence of –OH group in phenol increases the electron density at ortho and para position of the benzene ring due to the +R effect. As a result, nitronium electrophile can readily attack the benzene ring of phenols.

Page No 160:

Question 48:

In Kolbe’s reaction, instead of phenol, phenoxide ion is treated with carbon dioxide. Why?

Answer:

In phenoxide ion, the negative charge of oxygen is transferred to benzene ring through resonance. This helps the weak electrophile CO2 to easily get attached to the benzene ring, finally giving salicylic acid. Therefore, phenoxide ion is more reactive than phenol towards electrophilic substitution reaction and used in Kolbe’s reaction.

Page No 160:

Question 49:

Dipole moment of phenol is smaller than that of methanol. Why?

Answer:

In case of phenol, the  –OH group is attached to the carbon of benzene ring, which is sp2 hybridised and thus, benzene ring produces an electron withdrawing effect. Whereas, in case of methanol, the –OH group is attached to the carbon atom which is sp3 hybridised and thus, it produces an electron releasing effect. Hence, the C–O bond in phenol is less polar than the C–O bond in methanol and the dipole moment of phenol is smaller than that of methanol.

Page No 160:

Question 50:

Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether can’t be prepared by this method. Explain.

Answer:

Alkoxides are not only nucleophiles but also strong bases. When they react with tertiary alkyl halides, they leads to elimination reaction.
When tert-butyl-bromide react with sodium-tert-butoxide, elimination takes place instead of substitution. Thus, isobutylene is formed instead of di-tert-butyl ether.

Page No 160:

Question 51:

Why is the C — O — H bond angle in alcohols slightly less than the tetrahedral angle whereas the C — O — C bond angle in ether is slightly greater?

Answer:

The tetrahedral bond angle is 109.5°. The C — O — H bond angle in alcohols is slightly less than tetrahedral angle due lone pair -lone pair repulsions between the unshared electron pairs of oxygen. For example, the C — O — H bond angle in methanol is 108.9°.
But in case of ethers, the four electron pairs, i.e., the two bond pairs and two lone pairs of electrons on oxygen are arranged approximately in a tetrahedral arrangement and the C — O — C bond angle is slightly greater than tetrahedral angle because of greater repulsion between the two bulky alkyl groups. The C — O — C bond angle is 111.7° in ethers.

Page No 160:

Question 52:

Explain why low molecular mass alcohols are soluble in water.

Answer:

The solubility of alcohols in water depends upon the extent of hydrogen bonding. The alcohols with lower molecular mass will have smaller hydrocarbon part (hydrophobic part) and thus, the tendency to form hydrogen bonds is much higher in such alcohols and therefore, they are more soluble in water.

Page No 160:

Question 53:

Explain why p-nitrophenol is more acidic than phenol.

Answer:

The nitro group in p-Nitrophenol is an electron withdrawing group. So, it produces –I and –R effect. Thus, reducing the electron density on the oxygen of the O — H bond of phenol and due to the effective delocalisation of negative charge in phenoxide ion, making it more acidic.

Page No 160:

Question 54:

Explain why alcohols and ethers of comparable molecular mass have different boiling points?

Answer:

Ethers have low polarity in comparison to alcohols. As a result, they do not show association by inter-molecular hydrogen bonding. Therefore, ethers have low boiling points than alcohols of comparable molecular masses.

Page No 160:

Question 55:

The carbon-oxygen bond in phenol is slightly stronger than that in methanol. Why?

Answer:

In phenol the oxygen is attached to sp2 hybridised and is more electro-negative as compared to sp3 hybridised carbon atom in methanol. As a result, the C — O bond in phenols is more polar as compared to C — O bond in methanol. Also, in phenol, the unshared electron pairs over oxygen conjugates with carbon of benzene ring, which develops a partial double bond character of  C — O bond. 

But no such conjugation is observed in methanol. Hence, the carbon-oxygen bond in phenol is slightly stronger than that in methanol.

Page No 160:

Question 56:

Arrange water, ethanol and phenol in increasing order of acidity and give reason for your answer.

Answer:

Phenoxide ion obtained after the removal of H+ from phenol and is resonance stabilized.

Ethoxide ion will be obtained by the removal of H+ and is destabilised by +I effect of ethyl group which increases electron density on oxygen tending to decrease the polarity of O-H bond. 
 
So, ethanol is less acidic than phenol.
Also, water is a better proton donor (i.e., stronger acid) than ethanol.
C2H5O- Base+ H-O····-HAcid  C2H5OH Conjugate acid + O-HConjugate base
In the above reaction, it is observed that an ethoxide ion is a better proton acceptor than hydroxide ion, which suggests that ethoxide is a stronger base than hydroxide.
Hence, the increasing of acidity is ethanol < water < phenol.

Page No 160:

Question 57:

Match the items of Column I and Column II in the given question.
Match the structures of the compounds given in Column I with the name of the compounds given in Column II.

Column I Column II
(i)  (a) Hydroquinone
(ii)  (b) Phenetole
(iii)  (c) Catechol
(iv)  (d) o-Cresol
(v)  (e) Quinone
(vi)  (f) Resorcinol
  (g) Anisole

Answer:

Column I Column II
(i)  (d) o-cresol
(ii)  (c) Catechol
(iii)  (f) Resorcinol
(iv)  (a) Hydroquinone
(v)  (g) Anisole
(vi)  (b) Phenetole



Page No 161:

Question 58:

Match the items of Column I and Column II in the given question.
Match the structures of the compounds given in Column I with the name of the compounds given in Column II.

Column I Column II
(i) CH3−O−CH3                   (a)  + CH3I
Column I Column II
(i) CH3−O−CH3                   (a)  + CH3I

Answer:

  Column I   Column II
(i) (d)
(ii) (e)
(iii) (b)
(iv) (a)



Page No 162:

Question 59:

Match the items of Column I and Column II in the given question.

Match the items of column I with items of column II.
 

Column I Column II
(i) Antifreeze used in car engine (a) Neutral ferric chloride
(ii) Solvent used in perfumes (b) Glycerol
(iii) Starting material for picric acid (c) Methanol
(iv) Wood spirit (d) Phenol
(v) Reagent used for detection of phenolic group (e) Ethylene glycol 
(vi) By product of soap industry used in cosmetics (f) Ethanol 

Answer:

 

Column I Column II
(i) Antifreeze used in car engine (e) Ethylene glycol
(ii) Solvent used in perfumes (f) Ethanol
(iii) Starting material for picric acid (d) Phenol
(iv) Wood spirit (c) Methanol
(v) Reagent used for detection of of phenolic group (a) Neutral ferric chloric
(vi) By product of soap industry used in cosmetics (b) Glycerol

(i) A small percentage of ethylene glycol is used as antifreeze in car engines.
(ii) Ethanol is used as a solvent in perfumes as it can dissolve fatty and waxy substances very easily. These fatty and waxy substances provide odour to perfumes. Apart from being a good solvent, it cause less irritation to the skin.
(iii) On nitration with conc. HNO3, phenol is converted into picric acid.

(iv) 
Methanol is known as wood spirit as it is obtained by destructive distillation of wood.
(v) Neutral ferric chloride changes its color to purple when treated with phenol. This test is used as a detection test for phenols.
(vi) Soaps are prepared by the reaction of fatty acids with NaOH. 

Page No 162:

Question 60:

Match the items of Column I and Column II in the given question.

Match the items of column I with items of column II.
 

Column I Column II
(i) Methanol (a) Conversion of phenol to o-hydroxysalicylic acid
(ii) Kolbe’s reaction  (b) Ethyl alcohol
(iii) Williamson’s synthesis (c) Conversion of phenol to salicylaldehyde
(iv) Conversion of 2° alcohol to ketone  (d) Wood spirit
(v) Reimer-Tiemann reaction   (e) Heated copper at 573 K
(vi) Fermentation  (f) Reaction of alkyl halide with sodium alkoxide

Answer:

 

Column I Column II
(i) Methanol (d) Wood spirit
(ii) Kolbe’s reaction (a) Conversion of phenol to o-hydroxysalicylic            acid
(iii) Williamson’s synthesis (f) Reaction of alkyl halide with sodium alkoxide
(iv) Conversion of 2° alcohol           to ketone (e) Heated copper at 573 K
(v) Reimer-Tiemann reaction (c) Conversion of phenol to salicylic acid
(vi) Fermentation (b) Ethyl alcohol

Explanation:
(i) Methanol is prepared by destructive distillation of wood and is known as wood spirit.
(ii) In Kolbe's reaction, phenol is converted to o-hydroxysalicylic acid.


(iii) 
In Williamson's synthesis, an alkyl halide reacts with sodium alkoxide to produce an ether.
R – X + R-O····-Na+ → ROR + NaX

(iv) Secondary alcohol loses hydrogen (dehydrogenation) on heating it with copper at 573 K  to form a ketone.


(v) 
Reimer-Tiemann reaction is used for the synthesis of salicylaldehyde using phenol.



(vi) 
Ethanol is prepared by the fermentation of sugars.



Page No 163:

Question 61:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: Addition reaction of water to but-1-ene in acidic medium yields butan-1-ol
Reason: Addition of water in acidic medium proceeds through the formation of primary carbocation. 

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion.

Answer:

The product of addition reaction of water to but-1-ene is butan-2-ol because the reaction proceeds in acidic medium through the formation secondary carbocation in accordance with Markovnikov’s rule.
CH2=CH-CH2-CH3But-1-ene +H2O H+ CH3-CHOH-CH2-CH3Butan-2-ol

Hence, the correct answer is option (ii).

Page No 163:

Question 62:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: p-nitrophenol is more acidic than phenol.
Reason: Nitro group helps in the stabilisation of the phenoxide ion by dispersal of negative charge due to resonance.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion

Answer:

The nitro group in p-nitrophenol is an electron withdrawing group. So, it produces –I and –R effect. Thus, reducing the electron density on the oxygen of the O — H bond of phenol and due to the effective delocalisation of negative charge in phenoxide ion, making it more acidic than phenol.


Hence, the correct answer is option (i).

Page No 163:

Question 63:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: IUPAC name of the compound is 2-Ethoxy-2-methylethane.
Reason: In IUPAC nomenclature, ether is regarded as hydrocarbon derivative in which a hydrogen atom is replaced by — OR or — OAr group [where R = alkyl group and Ar = aryl group]

​(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion

Answer:

According to IUPAC system of nomenclature, ethers are regarded as hydrocarbon derivatives in which a hydrogen atom is replaced by an –OR or –OAr group, where R and Ar represent alkyl and aryl groups, respectively. The larger (R) group is chosen as the parent hydrocarbon.

The IUPAC name of the compound is 2-propoxypropane.

Hence, the correct answer is option (iv).

Page No 163:

Question 64:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: Bond angle in ethers is slightly less than the tetrahedral angle.
Reason: There is a repulsion between the two bulky (—R) groups.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion.

Answer:

In ethers, the four electron pairs, i.e., the two bond pairs and two lone pairs of electrons on oxygen are arranged approximately in a tetrahedral arrangement. The bond angle is slightly greater than the tetrahedral angle (109o-28′) due to the repulsive interaction between the two bulky (–R) groups. The C — O — C bond angle is 111.7° in methoxymethane.


Hence, the correct answer is option (iv).

Page No 163:

Question 65:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: Boiling points of alcohols and ethers are high.
Reason: They can form intermolecular hydrogen-bonding.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion.

Answer:

Alcohols of comparable molecular mass have higher boiling points than the corresponding ethers due to the formation of intermolecular hydrogen bonding in alcohols but not in ethers.


Hence, the correct answer is option (ii).



Page No 164:

Question 66:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: Like bromination of benzene, bromination of phenol is also carried out in the presence of Lewis acid.
Reason: Lewis acid polarises the bromine molecule.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion.

Answer:

The bromination  of benzene takes place in the presence of a Lewis acid, such as FeBr3, which polarises the bromine molecule. In case of phenol, the polarisation of bromine molecule takes place even in the absence of Lewis acid. It is due to the highly activating effect of –OH group attached to the benzene ring.

Hence, the correct answer is option (iv).

Page No 164:

Question 67:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: o-Nitrophenol is less soluble in water than the m- and p-isomers.
Reason: m- and p-Nitrophenols exist as associated molecules.

​(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion

Answer:

 o-Nitrophenol undergoes intramolecular hydrogen bonding. As a result, it does not from hydrogen bonds with water and is less soluble than the m- and p-isomers.


But m- and p-Nitrophenol forms hydrogen bonds with water. Due to the presence of intermolecular H-bonding, m-Nitrophenol and p-Nitrophenol exists as associated molecules.


Hence, the correct answer is option (v).

Page No 164:

Question 68:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: Ethanol is a weaker acid than phenol.
Reason: Sodium ethoxide may be prepared by the reaction of ethanol with aqueous NaOH.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion

Answer:

Phenol is more acidic than ethanol as phenoxide ion is stabilised by resonance while ethoxide ion is destabilised by electron releasing effect of ethyl group and the negative charge is localised on oxygen. This decreases the acidic strength of ethanol.


Alcohols and phenols react with active metals such as sodium, potassium and aluminium to yield corresponding alkoxides/phenoxides and hydrogen. Sodium ethoxide can be prepared by the reaction of ethanol with sodium as follows:

Hence, the correct answer is option (iii).

Page No 164:

Question 69:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: Phenol forms 2, 4, 6–tribromophenol on treatment with Br2 in carbon disulphide at 273K.
Reason: Bromine polarises in carbon disulphide.

​(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion. 

Answer:

In case of phenol, the polarisation of bromine molecule takes place even in the absence of Lewis acid. It is due to the highly activating effect of –OH group attached to the benzene ring.
Phenol forms 2, 4, 6–tribromophenol on treatment with Br2 in water. 


But phenol on treatment with Br2 in the presence of CS2 form o-Bromophenol and p-Bromophenol.



Hence, the correct answer is option (ii).

Page No 164:

Question 70:

In the following question a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

Assertion: Phenols give o- and p-nitrophenol on nitration with conc. HNO3 and H2SO4 mixture
Reason: —OH group in phenol is o–, p– directing.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion is wrong statement but reason is correct statement.
(v) Both assertion and reason are correct statements but reason is not correct explanation of assertion. 

Answer:

Phenol gives o-, p- nitrophenol on nitration with dil. HNO3 and H2SO4 at 298 K.


The –OH group attached to the benzene ring in phenol activates it towards electrophilic substitution. Also, it directs the incoming group to ortho and para positions in the ring as these positions become electron rich due to the resonance effect caused by –OH group. Thus, — OH group in phenol is ortho-pare directing.

Hence, the correct answer is option (iv).

Page No 164:

Question 71:

Write the mechanism of the reaction of HI with methoxybenzene.

Answer:

The mechanism of the reaction of HI with methoxybenzene is as given below:
Protonation of anisole gives methylphenyl oxonium ion.



In this ion, the bond between O—C6H5 is stronger than the bond between O—CH3. This is due to partial double bond character in O — C6H5 due to resonance between the lone pair of electrons on the O atom and the sp2 hybridised carbon atom of the phenyl group. Therefore, I prefers to attack by breaking the weaker O—CHbond. Thus, forming methyl iodide and phenol.



 

Page No 164:

Question 72:

(a) Name the starting material used in the industrial preparation of phenol.
(b) Write complete reaction for the bromination of phenol in aqueous and non aqueous medium.
(c) Explain why Lewis acid is not required in bromination of phenol?

Answer:

(a) Cumene (isopropyl benzene) is the starting material used in the industrial preparation of phenol.



(b) Reactions for bromination of phenol are as follows:
(i) In aqeous medium



(ii) In non-aqeous medium



(c) In case of phenol, the highly activating effect of –OH group attached to the benzene ring polarises the bromine molecule to form Br+ ion, which acts as an electrophile. Therefore, Lewis acid is not required in the bromination of phenol.

Page No 164:

Question 73:

How can phenol be converted to aspirin?

Answer:

Phenol is first converted into salicylic acid using sodium hydroxide and carbon dioxide reagents.


The salicylic acid is treated with acetic anhydride. On acetylation of salicylic acid, aspirin is formed.
 

Page No 164:

Question 74:

Explain a process in which a biocatalyst is used in industrial preparation of a compound known to you.

Answer:

Biocatalysts are the substances obtained from some natural sources that include enzymes from biological source or a whole cell. Enzymes work in enhancing the rate of a chemical reaction.
The process of fermentation of molasses yield ethanol. It occurs by breaking down of large molecules into simple ones in the presence of enzymes. The source of enzymes is yeast in fermentation. Yeast consists of invertase and zymase enzyme.
The enzyme invertase hydrolyses sucrose to glucose and fructose.
C12H22O12Sucrose+H2OInvertaseC6H12O6Glucose+C6H12O6Fructose
Whereas, enzyme zymase converts glucose into ethanol.
C6H12O6Zymase2C2H5OH+2CO2
For wine making, the grapes are the main source of sugar and yeast. As the grapes ripen, the content of sugar increases and the yeast grows on the outer skin. When grapes are crushed, sugar and the enzyme come in contact and fermentation starts. Fermentation takes place in anaerobic conditions i.e. in absence of air. Carbon dioxide is released during fermentation
Further fermentation is inhibited by zymase once the percentage of alcohol exceeds 14 percent in wine.



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