Unit 11. Alcohols, Phenols and Ethers
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1 Unit 11. Alcohols, Phenols and Ethers One mark questions 1. Name the alcohol which is used for polishing wooden furniture. Ans: Ethanol 2. What are alcohols? Ans: Hydroxyl derivatives of aliphatic compounds are called alcohols. 3. What is the IUPAC name of? Ans: Ethane-1, 2-diol 4. Write the structure of 2-methyl cyclopentanol. Ans: 5. Name the simplest hydroxyl derivative of benzene. Ans: Phenol 6. What is the IUPAC name of Resorcinol? Ans: Benzene-1, 3-diol 7. What is the common name of CH 3 OC 2 H 5? Ans: Ethylmethyl ether 8. Write the formula of anisole. Ans: C 6 H 5 OCH 3 or 9. What is the IUPAC name of anisole? Ans: Methoxybenzene. 10. Write the IUPAC name of CH 2 = CH CH 2 OH Ans: prop-2-en-1-ol 1
2 11. Why is the bond angle in alcohols is slightly less than the tetrahedral angle? Ans: It is due to the repulsion between the unshared electron pairs of oxygen atom. 12. Why is the bond angle slightly greater than the tetrahedral angle in ethers? Ans: It is due to the repulsive interaction between the two bulky R groups or alkyl groups. 13. Name the product obtained when propene is subjected to acid catalysed hydration. Ans: Propan-2-ol or 2-propanol 14. In the reaction, Ans: Ethanol 15. In a reaction, H H C CH H O X Identify X. CH CH CH X Name the product X formed in the diporane 3 2 H2O 2/NaOH reaction. Ans: Propan-1-ol. 16. Write the chemical name of cumene. Ans: Isopropyl benzene. 17. The boiling point of alcohols is much higher than ethers and other classes of compounds with similar molecular masses. Give reason. Ans: Due to intermolecular hydrogen bonding in alcohols. 18. Give reason: Lower alcohols are soluble in water. Ans: Due to the formation of hydrogen bonds with water molecules. 19. Name the compound which is also known as carbolic acid. Ans: Phenol
3 20. Name the method by which O-nitrophenol and p-nitrophenol are separated. Ans: By steam distillation the two isomers are separated. 21. Ether is soluble in water. Give reason. Ans: Ether is soluble in water because oxygen of ether form hydrogen bonds with water molecule. Two Mark Questions 1. What happens when an aldehyde is reduced? Write the general reaction OR explain the reduction of aldehydes. Ans: Aldehydes on reduction by hydrogen in presence of catalyst like finely divided Nickel or platinum give the respective primary alcohols. RCHO H RCH OH Ni 2 2 Or Aldehydes on reduction in presence of sodium borohydride (NaBH 4 ) or lithium aluminium hydride (LiAlH 4 ) yield the respective primary alcohols. RCHO 2(H) RCH OH NaBH 4 or LiAlH An aldehyde reacts with Grignards reagent forming an inter immediate product which on hydrolysis gives primary alcohol. Name the aldehyde and write the chemical equation. Ans: The aldehyde is methanal or formaldehyde. HO 2 Reaction: HCHO + RMgX RCH 2 OMgX RCH 2 OH+MgX(OH) 3. How is phenol prepared from aniline? Write the equation. Ans: Aniline is treated with nitrous acid in presence of HCl at K, when benzene diazonium chloride is obtained. Which on warming with water or treating with dilute acids gives phenol. C H NH C H N NCl C H OH N HCl NaNO 2 H2O HCl 6 5 warm 6 5 2
4 4. What is meant by hydroboration oxidation reaction. Illustrate with an example. Ans: Diborane reacts with alkenes to give trialkyl boranes which is oxidized to alcohol by hydrogen peroxide in presence of sodium hydroxide. 3CH3 CH CH 2 (BH 3) 2 (CH3CH2CH 2) 3B Reaction OH 3CH CH CH OH B(OH) 3H2O Give two reactions that show acidic nature of phenol. Ans: Reaction (1) C 6 H 5 OH + Na C 6 H 5 ONa + H 2 (2) C 6 H 5 OH + NaOH C 6 H 5 ONa + H 2 O These two reactions prove that phenol is acidic. 6. Name the following reaction and predict the product X obtained. H 2SO 4 R COOH + RO-H X+ H 2 O Ans: The name of the reaction is esterification and product X is an ester with the formula R COOR. 7. When phenol is treated with acid chloride in presence of pyridine base, what is the product obtained. Write the equation. Ans: The reaction is C H OH RCOCl C H OCOR HCl pyridine The product is an ester. 8. Explain the dehydration of ethanol with equation. Ans: Ethanol undergoes dehydration by heating it with conc. H 2 SO 4 at 443 K. forming ethene. CH CH OH CH CH H O conc H2SO K Explain the dehydration of a secondary alcohol with equation. OR How is isopropyl alcohol converted to propene by dehydration reaction? Ans: Secondary alcohols like isopropyl alcohol undergo dehydration on heating with 85% phosphoric acid at 440 K. forming an alkene (propene)
5 85% H3PO4 Reaction CH3 CH CH3 CH 440 K 3 CH CH2 H2O OH 10. Explain the dehydration of tertiary alcohols. Ans: Tertiary alcohols undergo dehydration when heated with 20% H 3 PO 4 at 358 K forming the respective alkene. Reaction: 11. Complete the following reactions: Cu (a) RCH OH X (b) Cu X R C R 573 O Name X in both the reactions. Ans: Cu (a) RCH2OH RCHO X-Aldehyde 573 Cu (b) R CH OH R C R X = Secondary alcohol 573 R O 12. Explain the reaction of phenol with dil. nitric acid at 298 K. Write equation. Ans: Phenol reacts with dil. HNO 3 at 298 K forming O-nitrophenol and p- nitrophenol respectively. 13. How do you convert phenol to picric acid? Explain with equation. Ans: Phenol reacts with concentrated nitric acid forming picric acid or 2, 4, 6- trinitro phenol.
6 14. Explain the bromination of phenol forming ortho and para bromophenols with equation. Ans: Phenol reacts with bromine in CS 2 at 273 K forming ortho and para bromophenols respectively. 15. How is phenol converted to 2, 4, 6-tribromophenol? Explain with equation. Ans: Phenol reacts with bromine water forming a white ppt of 2, 4, 6-trinitrophenol 16. Explain Kolbe s reaction with equation. OR What happens when sodium phenate is treated with carbon dioxide? Write equation and name the reaction. Ans: Sodium phenate is treated with carbon dioxide and the product on acidification forms salicylic acid. This reaction is called Koble s reaction.
7 17. How is phenol converted to benzene? Write the equation. Ans: Phenol is converted to benzene on heating with zinc dust. 18. Explain Reimer Tiemann reaction with equation. Ans: Phenol is treated with chloroform and sodium hydroxide solution. The product on acidification forms salicyl aldehyde. 19. Explain the oxidation of phenol with equation. Ans: Phenol undergoes oxidation with acidified sodium dichromate forming benzoquinone. 20. How is diethyl ether or ethoxy ethane prepared from ethanol? Write equation. Ans: Ethanol is heated with conc. H 2 SO 4 to 413 K when ethoxy ethane is obtained. 2C 2 H 5 OH C 2 H 5 OC 2 H 5 +H 2 O
8 21. Explain Wilhamson synthesis with equation. Ans: An alkyl halide reacts with sodium alkoxide forming the respective ethers. By this method both symmetrical and unsymmetrical ethers can be prepared. R X R ONa R O R NaX 22. Identify A and B in the following reactions and name the product obtained. (A) (B) Ans: (A) (B) 23. Explain the reaction of anisole with HI. Write the equation. Ans: Anisole reacts with HI forming phenol and methyl iodide. C6H5O CH3 HI C6H5OH CH3I 24. Explain the bromination of anisole with equation. Ans: Anisole (methoxy benzene) undergoes bromination with bromine in ethanoic acid in absence of FeBr 3 catalyst forming O-bromoanisole and p-bromoanisole respectively.
9 25. Explain the Friedel crafts reaction of anisole with equation. Ans: Anisole reacts with chloromethane in presence of anhydrous aluminium chloride as catalyst forming 2-methoxy toluene and 4-methoxy toluene. OR Anisole reacts with acetyl chloride in presence of anhydrous aluminium chloride forming 2-methoxy acetophenone and 4 methoxy acetophenone. 26. Explain the reaction of anisole with a mixture of conc. H 2 SO 4 and conc. HNO 3 or Explain the nitration of anisole with equation. Ans: Anisole reacts with a mixture of conc. Sulphuric acid and conc. Nitric acid forming ortho nitro anisole and paranitroanisole.
10 III. Three Mark Questions 1. Give three reasons that phenols are more acidic than alcohols. Ans: (1) In phenol, the OH group is attached to sp 2 hybridised carbon which is more electronegative, hence the OH bond becomes more polar. (2) Due to resonance is phenol, oxygen gets a positive charge and this increases the polarity of the O H bond. (3) Delocalisation of negative charge in phenoxide ion makes phenoxide ion more stable than phenol favouring the ionization of phenol. 2. Explain the mechanism of dehydration of ethanol to ethane. Ans: The dehydration of ethanol to ethane occurs in the following three steps, when heated with conc. H 2 SO 4 at 443 K. CH CH OH CH CH H O conc H2SO K 2 2 2
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