Alkyl halide (haloalkane)

Syllabus according to NEB, Nepal.

1. Alkyl Halide (Haloalkane) Dilip Ghimire

2. Introduction R-X Alkyl Halide Haloalkane

3. Classification According to the number of halogen present Mono Haloalkane Example: CH 3 -CH 2 - X [Where X can be Cl, F, Br or I] Dihaloalkane Example: X -CH 2 -CH 2 - X , [Where X can be Cl, F, Br or I] Trihaloalkane Example: X -CH 2 -CH X -CH 2 - X , [Where X can be Cl, F, Br or I]  

4. According to class of carbon Primary alkyl halide (1 )

5. Secondary alkyl halide (2 )

6. Tertiary alkyl halide (3 )

7. Nomenclature of Haloalkanes Common Name

8. Formula Common Name 1. Methyl chloride 2. Ethyl chloride 3. Ethyl bromide 4. Ethyl iodide 5. n-propyl chloride 6. Isopropyl chloride Formula Common Name Methyl chloride Ethyl chloride Ethyl bromide Ethyl iodide n-propyl chloride Isopropyl chloride

9. Isopropyl chloride t-butyl chloride

10. IUPAC Nomenclature R-X Haloalkane

11. To give IUPAC Name You ask yourself ! What is word root? What is primary suffix? What is secondary suffix? What are prefixes? What are their positions?

12. Formula IUPAC Name 1. Chloromethane 2. Chloroethane 3. Bromoethane 4. Iodoethane 5. Chloropropane 6. 2-chloropropane Formula IUPAC Name Chloromethane Chloroethane Bromoethane Iodoethane Chloropropane 2-chloropropane

13. Write the isomers of with their Common name and IUPAC names.  

14.   Chlorobutane 2-chlorobutane n-butyl chloride sec-butyl chloride 1-chloro-2-methylpropane 2-chloro-2-methylpropane isobutyl chloride t- butylchloride 1 2 3 4

15. Isomerism Chain isomerism 1-chlorobutane 1-chloro-2-methylpropane Position isomerism 1-chlorobutane 2-chlorobutane

16. General methods of preparation From alkane Bromination is like chlorination. Iodination is reversible To make irreversible  

18. CH 3 CH 2 CH 3 + Cl 2 propane  

19. CH 3 CH 2 CH 3 + Cl 2 CH 3 CH 2 CH 2 -Cl + CH 3 CHCH 3 propane n -propyl chloride Cl isopropyl chloride 45% 55% gives a mixture of both the possible alkyl halides!   

20. From alkene (X=Cl, Br, I) Ethene chloroethane  

21. From alkene (X=Cl, Br, I) Ethene chloroethane Markovnikov’s addition propene 2-chloropropane Peroxide effect  

22. From alkene (X=Cl, Br, I) Ethene haloethane Markovnikov’s addition [HX where X= Cl, Br, and I] propene 2-chloropropane Peroxide effect [only for HBr] propene 1-bromopropane  

23.   HBr HCl HCl HBr HBr Peroxide Peroxide H 2 O 2 A B C D E

24.   HBr HCl HCl HBr HBr Peroxide Peroxide H 2 O 2         Br  

25. From alcohol (Lucas reagent HCl +ZnCl 2 )   t-butyl chloride t-butyl alcohol

26. (Lucas reagent HCl +ZnCl 2 ) thionyl chloride  

27.   E C             F D B A

28.   Cl 2 /sunlight HCl HCl / ZnCl 2 PCl 5 Red P + Cl 2 SOCl 2 / pyridine

29.               Cl 2 /sunlight HCl HCl / ZnCl 2 PCl 5 Red P + Cl 2 SOCl 2 / pyridine

30. Physical properties State: Except chloromethane (B.P. -24 ), haloalkanes are sweet-smelling liquids. Solubility: Boiling point: Hydrogen bonding: Hydrogen should be attached to NOF Near to that hydrogen there should be NOF in the same or different molecule.

31. Physical properties State: Except chloromethane (B.P. -24 ), haloalkanes are sweet-smelling liquids. Solubility: They are insoluble in water because they could not make hydrogen bond with water, but they are soluble in non-polar solvents. Boiling point: RI > RBr > RCl  

32. Increase in molecular mass increase the boiling point. Boiling point of covalent molecule depends upon van der Waals force of attraction (which in turn depends upon molecular size). Increase in van der Waals force of attraction increase the boiling point. For isomers boiling point decrease on branching.

33. Chemical Properties Nucleophilic Substitution reaction  

34.                 Aq KOH Alc. NH 3 KCN AgCN AgNO 2 CH 3 ONa KNO 2

35.                 A B C D E G F

36.                 Aq KOH Alc. NH 3 KCN AgCN AgNO 2 CH 3 ONa KNO 2

37. Hofmann’s ammonolysis Method Williamson’s Synthesis  

38. Reaction with aq KOH Alkyl halide react with aq. KOH to produce alcohol. Chloroethane ethanol Convert ethane into ethanol.  

39. Formula Common Name IUPAC Name Ethyl alcohol Ethanol 2. Ethyl amine Ethanamine 3. Ethyl cyanide Propanenitrile 4. Ethyl isocyanide Ethylcarbylamine 5. Ethyl nitrate Nitroethane 6. Ethyl nitrite Nitrosoethane 7. Ethyl methyl ether Methoxyethane Formula Common Name IUPAC Name Ethyl alcohol Ethanol Ethyl amine Ethanamine Ethyl cyanide Propanenitrile Ethyl isocyanide Ethylcarbylamine Ethyl nitrate Nitroethane Ethyl nitrite Nitrosoethane Ethyl methyl ether Methoxyethane

40. Ambident nucleophile Am=Equal bi = two Dent = teeth    

41. Reaction of alkyl cyanide Complete hydrolysis Partial Hydrolysis Reduction    

42. Convert Methane into ethanoic acid Methane into ethanamide Methane into ethanamine Ethane into propanamide  

43. A is chloromethane because methane on chlorination produce chloromethane A (chloromethane) react with alcoholic KCN to produce ethanenitrile (B) Ethanenitrile (B) on complete hydrolysis produce ethanoic acid .  

44. An organic compound A react with chlorine in presence of sunlight to produce B. B react with KCN to produce C which on complete hydrolysis produce propanamine . What is A?

45. Dehydrohalogenation/Elimination What is the product in the following reaction? A B  

46. Both the products will be formed but the major product is according to Saytzeef rule. It states that, “ If more than one elimination product is possible, the most substituted alkene is the most stable product (major product ).”

47. Wurtz reaction  

48.   Convert Methane into ethane Methane into ethene 1-bromopropane into 2-bromopropane and vice versa

49. Convert methane into ethene Convert 1-bromopropane into 2-bromopropane and vice versa  

50. If A and C are isomers identify A, B, and C with suitable chemical reactions.  

51. Convert ethane into but-2-ene.  

52. Reaction with Magnesium alkylmagnesium halide Grignard reagent