Recommended
Recommended
More Related Content
What's hot
What's hot (20)
Similar to Alkyl halide (haloalkane)
Similar to Alkyl halide (haloalkane) (20)
Recently uploaded
Recently uploaded (20)
Alkyl halide (haloalkane)
- 1. ALKYL HALIDE (HALOALKANE) Dilip Ghimire
- 3. CLASSIFICATION According to the number of halogen present • Mono Haloalkane Example: CH3-CH2-X [Where X can be Cl, F, Br or I] • Dihaloalkane Example: X-CH2-CH2-X, CH2X2 [Where X can be Cl, F, Br or I] • Trihaloalkane Example: X-CH2-CHX-CH2-X, CHX3 [Where X can be Cl, F, Br or I]
- 4. ACCORDING TO CLASS OF CARBON Primary alkyl halide (10)
- 5. Secondary alkyl halide (20)
- 6. • Tertiary alkyl halide (30)
- 8. Formula Common Name 1. 𝐶𝐻3 𝐶𝑙 Methyl chloride 2. 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 Ethyl chloride 3. 𝐶𝐻3 𝐶𝐻2 𝐵𝑟 Ethyl bromide 4. 𝐶𝐻3 𝐶𝐻2 𝐼 Ethyl iodide 5. 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝑙 n-propyl chloride 6. 𝐶𝐻3 𝐶𝐻 𝐶𝑙 𝐶𝐻3 Isopropyl chloride
- 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. 𝐶𝐻3 𝐶𝑙 Chloromethane 2. 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 Chloroethane 3. 𝐶𝐻3 𝐶𝐻2 𝐵𝑟 Bromoethane 4. 𝐶𝐻3 𝐶𝐻2 𝐼 Iodoethane 5. 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝑙 Chloropropane 6. 𝐶𝐻3 𝐶𝐻 𝐶𝑙 𝐶𝐻3 2-chloropropane
- 13. Write the isomers of 𝐶4 𝐻9 𝐶𝑙 with their Common name and IUPAC names.
- 14. C4H9 𝐶𝑙 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 R − H + Cl2 sunlight R − Cl + HCl CH3CH3 + Cl2 sunlight CH3CH2Cl + HCl Bromination is like chlorination. Iodination is reversible R − H + I2 ⇋ R − I + HI To make irreversible HI + HIO3 → H2O + I2
- 17. 𝐶𝐻4 + 𝐶𝑙2 𝑠𝑢𝑛𝑙𝑖𝑔ℎ𝑡 𝐶𝐻3 𝐶𝑙 𝑠𝑢𝑛𝑙𝑖𝑔ℎ𝑡 𝐶𝐻2 𝐶𝑙2 𝑠𝑢𝑛𝑙𝑖𝑔ℎ𝑡 𝐶𝐻𝐶𝑙3 𝑠𝑢𝑛𝑙𝑖𝑔ℎ𝑡 𝐶𝐶𝑙4
- 19. CH3CH2CH3 + Cl2 𝑠𝑢𝑛𝑙𝑖𝑔ℎ𝑡 CH3CH2CH2-Cl + CH3CHCH3 propane n-propyl chloride Cl isopropyl chloride 45% 55% gives a mixture of both the possible alkyl halides!
- 20. FROM ALKENE • CH2 = CH2 + HX → CH3CH2X (X=Cl, Br, I) Ethene chloroethane • CH3CH = CH2 + HCl →
- 21. FROM ALKENE • CH2 = CH2 + HX → CH3CH2X (X=Cl, Br, I) Ethene chloroethane • Markovnikov’s addition CH3CH = CH2 + HCl → CH3CH Cl CH3 propene 2-chloropropane •Peroxide effect CH3CH = CH2 + HBr organic peroxide
- 22. FROM ALKENE • CH2 = CH2 + HX → CH3CH2X (X=Cl, Br, I) Ethene haloethane • Markovnikov’s addition [HX where X= Cl, Br, and I] CH3CH = CH2 + HCl → CH3CH Cl CH3 propene 2-chloropropane •Peroxide effect [only for HBr] CH3CH = CH2 + HBr organic peroxide CH3CH2CH2Br propene 1-bromopropane
- 24. CH3CH = CH2 HBr HCl HCl HBr HBr Peroxide Peroxide H2O2 CH3CH Br CH3 CH3CH Cl CH3 CH3CH Cl CH3 CH3CH Br CH3 CH3CH2CH2Br
- 25. From alcohol • ROH + HX → RX + H2O • ROH + HCl ZnCl2 RCl + H2O (Lucas reagent HCl +ZnCl2) • CH3CH2OH + HBr → CH3CH2Br + H2O t-butyl chloride t-butyl alcohol
- 26. • ROH + HCl ZnCl2 RCl + H2O (Lucas reagent HCl +ZnCl2) • C2H5OH + PCl3 → C2H5Cl + H3PO3 • C2H5OH + PCl5 → C2H5Cl + POCl3 + HCl • C2H5OH + SOCl2 pyridine C2H5Cl + SO2 + HCl thionyl chloride
- 27. • CH3CH3 E C C2H5Cl • C2H5OH • CH2 = CH2 • C2H5OH • C2H5OH • C2H5OH F D B A
- 28. C2H5Cl Cl2/sunlight HCl HCl / ZnCl2 PCl5 Red P + Cl2 SOCl2 / pyridine
- 29. C2H5Cl • C2H5OH • CH2 = CH2 • CH3CH3 • C2H5OH • C2H5OH • C2H5OH Cl2/sunlight HCl HCl / ZnCl2 PCl5 Red P + Cl2 SOCl2 / pyridine
- 30. PHYSICAL PROPERTIES •State: Except chloromethane (B.P. -240), 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. -240), 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 𝐶𝐻3 𝐶𝑙 < 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 < 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝑙 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝑙 >
- 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 R − X + Nu: → R − Nu + X−
- 35. C2H5Cl C2H5OH C2H5NH2 C2H5NO2 C2H5 − O − N = O C2H5 − O − CH3 C2H5C ≡ N C2H5N ≡ C A B C D E G F
- 36. C2H5Cl C2H5OH + KCl C2H5NH2 + HCl C2H5NO2 + AgCl C2H5 − O − N = O + KCl C2H5 − O − CH3 + NaCl C2H5C ≡ N + KCl C2H5N ≡ C + AgCl Aq KOH Alc. NH3 KCN AgCN AgNO2 CH3ONa KNO2
- 37. HOFMANN’S AMMONOLYSIS METHOD •RX + NH3 → RNH2 + HX •RNH2 + RX → R2NH + HX •R2NH + RX → R3N + HX •R3N + RX → R4N+ X− • Williamson’s Synthesis • RX + R′ ONa → ROR′ + NaX
- 38. •Reaction with aq KOH Alkyl halide react with aq. KOH to produce alcohol. RX + aq. KOH → ROH + KX C2H5Cl + aq. KOH → C2H5OH + KCl Chloroethane ethanol •Convert ethane into ethanol. •CH3CH3 Cl2 uv A KOH B
- 39. Formula Common Name IUPAC Name 1. C2H5OH Ethyl alcohol Ethanol 2. C2H5NH2 Ethyl amine Ethanamine 3. C2H5C ≡ N Ethyl cyanide Propanenitrile 4. C2H5N ≡ C Ethyl isocyanide Ethylcarbylamine 5. C2H5NO2 Ethyl nitrate Nitroethane 6. C2H5 − O − N = O Ethyl nitrite Nitrosoethane 7. C2H5 − O − CH3 Ethyl methyl ether Methoxyethane
- 40. AMBIDENT NUCLEOPHILE • Am=Equal bi = two • Dent = teeth • RX + KCN → RCN + KX • RX + AgCN → RNC + Ag X − C ≡ N: • K+ − C ≡ N: • Ag − C ≡ N: • 𝑅𝑋 + 𝐾𝑁𝑂2 → 𝑅 − 𝑂 − 𝑁 = 𝑂 + 𝐾𝑋 • 𝑅𝑋 + 𝐴𝑔𝑁𝑂2 → 𝑅𝑁𝑂2 + 𝐴𝑔𝑋 𝑂 − 𝑁 = 𝑂 • 𝐾+ − 𝑂 − 𝑁 = 𝑂 • 𝐴𝑔 − 𝑂 − 𝑁 = 𝑂
- 41. REACTION OF ALKYL CYANIDE • Complete hydrolysis RCN + HCl + H2O → RCOOH 𝑐𝑎𝑟𝑏𝑜𝑥𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑 + NH4Cl • Partial Hydrolysis RCN + H2O conc HCl RCNH2 (𝑎𝑚𝑖𝑑𝑒) • Reduction RCN + H2 → Ni ∆ RCH2NH2 𝑎𝑚𝑖𝑛𝑒 RCN + H Zn−HCl or LiAlH4 RCH2NH2 𝐶𝐻3 𝐶𝑂𝑂𝐻 𝐴𝑐𝑒𝑡𝑖𝑐 𝑎𝑐𝑖𝑑 𝐸𝑡ℎ𝑎𝑛𝑜𝑖𝑐 𝑎𝑐𝑖𝑑 𝐶𝐻3 𝐶𝑂𝑁𝐻2 𝐴𝑐𝑒𝑡𝑎𝑚𝑖𝑑𝑒 𝐸𝑡ℎ𝑎𝑛𝑎𝑚𝑖𝑑𝑒 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝑁𝐻2 𝑃𝑟𝑜𝑝𝑦𝑙 𝑎𝑚𝑖𝑛𝑒 𝑃𝑟𝑜𝑝𝑎𝑛𝑎𝑚𝑖𝑛𝑒
- 42. CONVERT •Methane into ethanoic acid •Methane into ethanamide •Methane into ethanamine •Ethane into propanamide •CH4 𝐶𝑙2 & 𝑢𝑣 𝐴 𝐾𝐶𝑁 𝐵 𝑑𝑖𝑙.𝐻𝐶𝑙 𝐶 • 𝐴 𝐶𝑙2 & 𝑢𝑣 B 𝐾𝐶𝑁 C 𝑑𝑖𝑙.𝐻𝐶𝑙 𝑒𝑡ℎ𝑎𝑛𝑜𝑖𝑐 𝑎𝑐𝑖𝑑
- 43. • CH4 Cl2 & uv A KCN B dil.HCl C • A is chloromethane because methane on chlorination produce chloromethane • CH4 methane + Cl2 uv CH3Cl chloromethane + HCl • A (chloromethane) react with alcoholic KCN to produce ethanenitrile (B) • CH3Cl + KCN → CH3CN ethanenitrile + KCl • 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 • CH3CH2Cl 𝑐ℎ𝑙𝑜𝑟𝑜𝑒𝑡ℎ𝑎𝑛𝑒 + alc KOH → CH2 = CH2 𝑒𝑡ℎ𝑒𝑛𝑒 + KCl + H2O • What is the product in the following reaction? CH3CH2CH Cl CH3 2−𝑐ℎ𝑙𝑜𝑟𝑜𝑏𝑢𝑡𝑎𝑛𝑒 + alc KOH → CH3CH2CH 𝑏𝑢𝑡−1−𝑒𝑛𝑒 = CH2 CH3CH = CHCH3 𝑏𝑢𝑡−2−𝑒𝑛𝑒 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 •2𝑅 − 𝑋 + 2𝑁𝑎 dry ether 𝑅 − 𝑅 + 2𝑁𝑎𝑋 • 𝑅 − 𝑋 + 2𝑁𝑎 + 𝑋 − 𝑅 dry ether 𝑅 − 𝑅 + 2𝑁𝑎𝑋 • 2𝐶𝐻3 𝐶𝑙 𝑐ℎ𝑙𝑜𝑟𝑜𝑚𝑒𝑡ℎ𝑎𝑛𝑒 + 2𝑁𝑎 𝑑𝑟𝑦𝑒𝑡ℎ𝑒𝑟 𝐶𝐻3 𝐶𝐻3 𝑒𝑡ℎ𝑎𝑛𝑒 + 2𝑁𝑎 𝐶𝑙 • 𝐶𝐻3 𝐶𝑙 + 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 𝑁𝑎 ?
- 48. 𝐶𝐻3 𝐶𝑙 + 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 𝑁𝑎 𝐶𝐻3 𝐶𝐻3 + 𝐶𝐻3 𝐶𝐻2 𝐶𝐻3 + 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝐻3 Convert Methane into ethane Methane into ethene 1-bromopropane into 2-bromopropane and vice versa
- 49. • Convert methane into ethene • 𝐶𝐻4 𝐶𝑙2 𝑎𝑛𝑑 𝑢𝑣 𝐶𝐻3 𝐶𝑙 𝑁𝑎,𝑑𝑟𝑦𝑒𝑡ℎ𝑒𝑟 𝐶𝐻3 𝐶𝐻3 • 𝐶𝐻3 𝐶𝐻3 𝐶𝑙2,𝑢𝑣 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 𝑎𝑙𝑐 𝐾𝑂𝐻 𝐶𝐻2 = 𝐶𝐻2 𝑒𝑡ℎ𝑒𝑛𝑒 • Convert 1-bromopropane into 2-bromopropane and vice versa • 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐵𝑟 𝑎𝑙𝑐 𝐾𝑂𝐻 𝐶𝐻3 𝐶𝐻 = 𝐶𝐻2 𝐻𝐵𝑟 𝐶𝐻3 𝐶𝐻 𝐵𝑟 𝐶𝐻3 • 𝐶𝐻3 𝐶𝐻 𝐵𝑟 𝐶𝐻3 𝑎𝑙𝑐 𝐾𝑂𝐻 𝐶𝐻3 𝐶𝐻 = 𝐶𝐻2 𝐻𝐵𝑟 𝑝𝑒𝑟𝑜𝑥𝑖𝑑𝑒 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐵𝑟
- 50. • 𝐶𝐻4 𝐶𝑙2 𝑢𝑣 𝐶𝐻3 𝐶𝑙 𝑁𝑎 𝐶𝐻3 𝐶𝐻3 𝐶𝑙2 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 𝑎𝑙𝑐𝐾𝑂𝐻 𝐶𝐻2 = 𝐶𝐻2 • 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐵𝑟 𝑎𝑙𝑐 𝐾𝑂𝐻 𝐶𝐻3 𝐶𝐻 = 𝐶𝐻2 𝐻𝐵𝑟 𝐶𝐻3 𝐶𝐻 𝐵𝑟 𝐶𝐻3 • 𝐴 𝑎𝑙𝑐 𝐾𝑂𝐻 𝐵 𝐻𝐵𝑟 𝐶 𝑁𝑎 2,3 − 𝑑𝑖𝑚𝑒𝑡ℎ𝑦𝑙 𝑏𝑢𝑡𝑎𝑛𝑒 If A and C are isomers identify A, B, and C with suitable chemical reactions.
- 51. • Convert ethane into but-2-ene. • 𝐶𝐻3 𝐶𝐻3 𝐶𝑙2 𝑢𝑣 𝐶𝐻3 𝐶𝐻2 𝐶𝑙 𝑁𝑎 𝐶𝐻3 𝐶𝐻2 𝐶𝐻2 𝐶𝐻3 𝐶𝑙2 𝐶𝐻3 𝐶𝐻 𝐶𝑙 𝐶𝐻2 𝐶𝐻3 𝑎𝑙𝑐𝐾𝑂𝐻 𝐶𝐻3 𝐶𝐻 = 𝐶𝐻𝐶𝐻3
- 52. REACTION WITH MAGNESIUM • 𝑅𝑋 + 𝑀𝑔 𝑑𝑟𝑦 𝑒𝑡ℎ𝑒𝑟 𝑅𝑀𝑔𝑋 alkylmagnesium halide Grignard reagent