April 20, 2020

14. Haloalkanes and Haloarenes


2 & 3 Marks
1. Classify the following compounds in the form of alkyl, allylic, vinyl, benzylic halides.
    i) CH3 – CH = CH – Cl                                          ii) C6H5CH2I
    iii) CH3  CH CH3                                              iv) CH2 = CH – Cl
                      |
                     Br
2. Write the IUPAC Name of the following.
 

3. Write the Structure of the following compounds.
    i) 1-Bromo-4-ethyl cyclohexane     ii) 1,4-Dichlorobut-2-ene        iii) 2-Chloro-3-methyl pentane
4. Write short notes on the Nature of C - X bond in Haloalkane.
5. Give reasons for Polarity of C - X bond in Haloalkane.
6. Arrange the following Alkyl halide in Increasing order of Bond enthalpy of RX.
      CH3Br, CH3F, CH3Cl, CH3I
7. Mention any three methods of Preparation of Haloalkanes from Alcohols.
8. What happens when Ethanol reacts with HCl?
9. What is Lucas reagent?
10. What happens when tert-Butyl alcohol reacts with HI in the presence of KI and H3PO4?
11. Explain the Order of reactivity of Halo acids with Alcohol.
12. Explain the Order of reactivity of Alcohols with Halo acid.
13. What happens when Ethanol reacts with PCl5?
14. What happens when Ethanol reacts with PCl3?
15. What happens when Ethanol reacts with Sulphonyl chloride? Or What is Darzen's halogenations? Or Write short notes on Darzen’s process
16. What happens when Alkenes react with Halogen acids?
                                                                Peroxide
17. Complete: CH3 - CH = CH2 + HBr ------------> ?
18. What happens when Alkanes react with Halogens in the presence of Ultra violet light?
19. What happens on Chlorination of Methane in the presence of Ultra violet light?
20. Why Chlorination of Methane is not possible in dark?
21. What happens when Chloroalkane on heating with a concentrated solution of NaI in dry Acetone? Or What happens when Bromoalkane on heating with a concentrated solution of NaI in dry Acetone? Or What is Finkelstein reaction?
22. What happens when Bromoethane reacts with NaI in the presence of Acetone?
23. How will you Prepare n-Propyl iodide from n-Propyl bromide?
24. What happens when Chloroalkanes on Heating with Metallic fluorides like AgF, SbF3 or Hg2F2 Or What happens when Bromoalkanes on Heating with Metallic fluorides like AgF, SbF3 or Hg2F2 Or What is Swarts reaction?
25. What happens when Bromoethane reacts with AgF?
26. What happens when Silver salts of fatty acids are refluxed with Bromine in CCl4?
27. What is Hunsdicker reaction?
28. What happens when Silver propionate is refluxed with Bromine in CCl4?
29. Haloalkanes have Higher boiling point and Melting point than the parent Alkanes having the same number of Carbons. Why?
30. Explain the Order of boiling point and melting point of Haloalkanes.
31. Explain the Order of boiling points of chloro, bromo and iodo alkanes.
32. Explain the Order of boiling point and melting point of Mono Haloalkane.
33. Explain the Order of boiling point Isomeric Alkyl halides.
34. Haloalkanes are Soluble in Organic solvents, but Insoluble in Water. Why?
35. What happens when Haloalkane reacts with aqueous solution of KOH or moist Silver oxide?
36. What happens when Bromoethane reacts with aqueous solution of KOH?
37. What happens when Bromoethane reacts with moist Silver oxide?
38. What happens when Haloalkanes react with alcoholic Ammonia solution?
39. What happens when Bromoethane reacts with NH3?
40. What happens when Excess of Haloalkanes react with alcoholic Ammonia solution?
41. What is Ambident nucleophiles?
42. What happens when Haloalkanes react with alcoholic KCN solution?
43. What happens when Bromoethane reacts with KCN?
44. What happens when Haloalkanes react with alcoholic AgCN solution?
45. What happens when Bromoethane reacts with AgCN?
46. What happens when Haloalkanes react with alcoholic solution of NaNO2 or KNO2?
47. Predict the product when Bromoethane is treated with KNO2.
48. What happens when Haloalkanes react with alcoholic solution of AgNO2?
49. Predict the product when Bromoethane is treated with AgNO2.
50. What happens when Haloalkanes react with Sodium hydrogen sulphide?
                                                                   Alcohol / H2O
51. Complete: CH3 - CH2 - Br + NaSH -----------------------> ?
52. What happens when Haloalkanes react with Potassium hydrogen sulphide?
53. What happens when Haloalkane boiled with Sodium alkoxide? Or What is Williamson ether synthesis?
54. What happens when Bromoethane reacts with Sodium ethoxide?
55. Reagents and the conditions used in the reactions are given below. Complete the table by writing downthe Product and the Name of the reaction.
Reaction
Product
Name of the reaction
                                      Pyridine
CH3CH2OH + SOCl2 ------------>?



CH3CH2Br + AgF------------>?


                          Ether
C6H5Cl + Na ------------>?


56. What is SN2 Mechanism?
57. Which Alkyl halide from the following pair i) is Chiral ii) undergoes faster SN2 reaction?
  

58. What is SN1 Mechanism?
59. Account : t-Butyl chloride reacts with aqueous KOH by SN1 Mechanism while n-Butyl chloride reacts with SN2 Mechanism.
60. neo-Pentyl bromide undergoes Nucleophilic substitution reactions very slowly - Justify.
61. What are Elimination reactions?
62. State Saytzeff ’s Rule.
63. What is E2 reaction mechanism?
64. What is E1 reaction mechanism?
65. What happens when 2-Bromopropane treated with an alcoholic KOH?
66. What happens when tert-Butyl chloride treated with an alcoholic KOH?
67. What are Organometallic compounds?
68. What happens when Haloalkane reacts with active Metals like Na, Pb in the presence of dry Ether?
69. What happens when Bromoethane reacts with Li in the presence of Dry Ether?
70. What happens when Bromoethane reacts with Na in the presence of Dry Ether?
71. What happens when Bromoethane reacts with Pb in the presence of Dry Ether?
72. What happens when Haloalkanes are treated with Hydrogen in the presence of metal Catalyst like Nickel, Palladium or with Hydroiodic acid in the presence of Red Phosphorous?
73 What happens when Bromoethane reacts with Hydrogen in the presence of Ni or Pd?
74. What happens when Iodo ethane reacts with HI in the presence of Red P?
75. What are the Uses of Haloalkane?
76. What are the Uses of Chloroform?
77. What are the Uses of Iodoform?
78. What are the Uses of Carbon tetrachloride?
79. What is Pyrene? Give its Use.
80. How will you prepare Grignard reagent?
81. What happens when Bromoethane reacts with Mg metal in the presence of Dry Ether?
82. Why Grignard reagent should be prepared in anhydrous condition?
83. How will you Prepare Primary alcohol using Grignard reagent?
84. Starting from CH3MgI, how will you prepare Ethyl alcohol?
85. How will you Prepare Secondary alcohol using Grignard reagent?
86. Starting from CH3MgI, how will you prepare Iso propyl alcohol?
87. How will you Prepare Tertiary alcohol using Grignard reagent?
88. Starting from CH3MgI, how will you prepare Tert-Butylalcohol?
89. How will you Prepare Aldehyde using Grignard reagent?
90. Starting from CH3MgI, how will you prepare Acetaldehyde?
91. How will you Prepare Ketone using Grignard reagent?
92. What happens when Acetyl chloride is treated with excess of CH3MgI? Or
      Starting from CH3MgI, how will you prepare Acetone?
93. How will you Prepare Carboxylic acids using Grignard reagent?
94. Starting from CH3MgI, How will you prepare Acetic acid?
95. How will you Prepare Esters using Grignard reagent?
96. Starting from CH3MgI, how will you prepare Ethyl acetate?
97. How will you Prepare Higher Ethers using Grignard reagent?
98. Starting from CH3MgI, how will you prepare Ethyl methyl ether?
99. How will you Prepare Alkyl cyanide using Grignard reagent?
100. Starting from CH3MgI, how will you prepare Methyl cyanide?
101. What happens when Compounds which contain active Hydrogen atom like Water, Alcohols and Amines react with Grignard reagents? Or How will you Prepare Alkanes using Grignard reagent?
102. Starting from CH3MgI, how will you prepare Methane?
103. Why is it necessary to avoid even traces of moisture during the use of Grignard reagent?
104. Write short notes on the Nature of C - X bond in Haloarenes.
105. What is Sandmeyer reaction?
106. What is Gattermann reaction?
107. What is Balz - Schiemann reaction?
108. Write short notes on Raschig process. Or How is Chloro benzene Commercially prepared?
109. How does Chlorobenzene react with Sodium in presence of Ether? What is the Name of the reaction?
110. Account : p-Dichloro benzene has Higher melting point than those of o-and m-Dichlorobenzene.
111. Haloarenes are insoluble in water. Why?
112. Halo arenes do not undergo Nucleophilic substitution reaction readily. Why?
113. Write short notes on Dow’s Process.
114. What happens when Chlorobenzene reacts with NH3?
115. What happens when Chlorobenzene reacts with CuCN in the presence of Pyridine?
116. What is Wurtz - Fittig reaction?
117. What is Fittig reaction?
118. How will you Prepare Biphenyl? Or Explain the Preparation of Biphenyl.
119. Write short notes on Friedel - Crafts alklation.
120. What happens when Chlorobenzene reacts with Hydrogen in the presence of Ni-Al / NaOH?
                                                      THF
121. Complete : C6H5Cl + Mg ------------> ?
122. What happens when Haloarenes react with Magnesium in Tetra hydrofuran (THF)?
123. What are the Uses of Chloro benzene?
124. Haloalkanes undergo Nucleophilic substitution reaction whereas Haloarenes undergo Electrophilic substitution reaction. Comment.
125. What happens on treating Acetaldehyde with PCl5?
126. What happens on adding Hydrogen chloride to Acetylene?
127. What happens on addition of Chlorine to Ethylene?
128. What is the action of PCl5 on Ethylene glycol?
129. What is the action of HCl on Ethylene glycol?
130. What happens when gem-Dihalides on hydrolysis with aqueous KOH?
131. What happens when Ethylidene dichloride on hydrolysis with aqueous NaOH?
132. What happens when vic-Dihalides on hydrolysis with aqueous NaOH?
133. What happens when Ethylene dichloride on hydrolysis with aqueous KOH?
134. How can you Distinguish the gem-Dihalides from vic-Dihalides?
135. What happens when gem-Dihalides on treatment with Zinc dust in Methanol?
136. What happens when Ethylidene dichloride on treatment with Zinc dust in Methanol?
137. What happens when vic-Dihalides on treatment with Zinc dust in Methanol?
138. What happens when Ethylene dichloride on treatment with Zinc dust in Methanol?
139. What happens when gem-Dihalides and vic-Dihalides on treatment with alcoholic KOH?
140. What happens when Ethylidene dichloride on treatment with alcoholic KOH?
141. What happens when Ethylene dichloride on treatment with alcoholic KOH
142. What are the Uses of Methylene chloride?
143. What are Trihaloalkane?
144. Explain the Preparation of Chloroform. Or How is Chloroform Prepared in the Laboratory?
145. Write a note on Haloform reaction.
146. Why is Chloroform used as an Anaesthetic?
147. Which makes Chloroform unfit for use as Anaesthetic?
148. What happens when Chloroform reacts with Oxygen in the presence of Sunlight? Or
        What happens when Chloroform is exposed to light and air?
149. Chloroform is kept with a little Ethyl alcohol in a Dark coloured bottle. Why?
150. What happens when Chloroform reacts with Zinc and HCl in the presence of Ethyl alcohol?
151. What is Chloropicrin? What is its Use?
152. How can you Prepare Chloropicrin? Or Explain the Preparation of Chloropicrin.
                                                            Δ
153. Complete : CHCl3 + HNO3 ------------> ?
154. What happens when Chloroform reacts with Aliphatic Primary amine or Aromatic Primary amine and alcoholic caustic potash?
155. Write a note on Carbylamine reaction.
156. Write a characteristic Test for Primary amine and explain with Chemical reaction.
157. The reaction of Methane with excess of Chlorine in the presence of Sunlight.
158. Write a Chemical reaction useful to prepare Carbon tetrachloride from Carbon disulphide.
                                                      Δ           
159. Complete : CCl4 + H2O ------------> ?
160. What happens when Carbon tetrachloride reacts with Hot water or with Hot water vapour?
161. What happens when Carbon tetrachloride is reduced by Iron powder in dilute HCl medium?
162. Write a note on Swartz reaction. Or Explain the Preparation of Freon - 12.
163. Write a Chemical reaction useful to prepare Freon - 12 from Carbon tetrachloride.
164. What are Freons? Discuss their Uses and Environmental effects.
165. Explain the Preparation of DDT.
166. What is the IUPAC name of the insecticide DDT? Why is their use banned in most of the countries?
5 Marks
1. Classify the various Organic Halo compounds.
2. What are Haloalkanes? How are they Classified? Give examples.
3. Describe the General methods of Preparation of Haloalkanes.
4. Explain the Physical properties of Haloalkanes.
5. Write all possible Chain isomers with molecular formula C5H11Cl.
6. Write down the possible Isomers of C5H11Br. Give their IUPAC name and Common name.
7. Explain the Chemical properties of Haloalkanes.
8. Discuss the Nucleophilic substitution reaction of Haloalkanes.
9. Describe the Mechanism of Nucleophilic substitution reactions of Halo organics.
10. Explain SN2 Mechanism.            
11. Explain SN1 Mechanism.
12. Explain the mechanism of SN1 reaction by highlighting the Stereochemistry behind it.
13. Compare SN1 and SN2 reaction mechanisms.
14. Describe the Mechanism of Elimination reactions of Halo organics.
15. Explain E2 reaction mechanism.
16. Explain E1 reaction mechanism.
17. Compare E1 and E2 reaction mechanisms.
18. In an experiment Ethyl iodide in Ether is allowed to stand over Magnesium pieces. Magnesium dissolves and product is formed.
      a) Name the Product and write the Equation for the reaction.
      b) Why all the reagents used in the reaction should be dry? Explain.
      c) How is Acetone prepared from the product obtained in the experiment?
19. Explain the Synthetic uses of Grignard reagent.
20. What are Haloarenes? How are they Classified? Give examples.
21. Describe the General methods of Preparation of Haloarenes.
22. Explain the Physical properties of Haloarenes.
23. Explain the Chemical properties of Haloarenes.
24. Discuss the Aromatic Nucleophilic substitutions reaction of Chlorobenzene.
25. Discuss the Aromatic Electrophilic substitutions reaction of Chlorobenzene.
26. What are Poly halogen compounds? How are they classified? Give examples.
27. Describe the Preparation of Ethylidene dichloride (1,1-Dichloro ethane).
28. Describe the Preparation of Ethylene dichloride (1,2-Dichloro ethane).
29. Explain the Preparation of Methylene chloride (Di chloromethane).
30. Describe the Chemical properties of Chloroform.
31. Explain the Preparation of Carbon tetrachloride.
32. Discuss about Nomenclature of Freons.
33. What are the Uses of DDT?

Problems
Name the Organic Halo compounds according to IUPAC system, Derive Structure from the IUPAC Name, Identifying Compounds & Explain the reactions.

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