Alkyl halide organic chemistry pharmacy

1. Amit Z Chaudhari
ALKYL HALIDE

2. C O N T E N T
2018 2
- Definition
- Classification
- General methods of preparation
- General reactions
- SN reaction
- Use

3. D e f i n a t i o n
3
compounds in which halogen attached to C.
Synonym: Halo alkanes
Gen. formula: R-X
where X = F, Cl, Br, I
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4. C l a s s i f i c a t i o n
4
- Primary, secondary and tertiary alkyl halide
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5. P r e p a r a t i o n
5
- Halogenation of alkane
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Refer : Bahal & bahl
or
morrison and boyd

6. P r e p a r a t i o n
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7. R e a c t i o n s
7
- SN reaction
- Dehydrohalogenation (1,2-elimination) reaction.
- Grignard reaction
Covered in
preparation
of Alkenes
2018

8. R e a c t i o n s
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Dehydrohalogenation (1,2-elimination) reaction.

9. R e a c t i o n s
9
Grignard reaction
e.g.
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10. 1
Substitution Nucleophilic reaction
SN r e a c t i o n
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11. 1
General rxn
Application
SN r e a c t i o n
Williamson
ether
synthesis
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12. 1
General rxn- exercise
1. Predict the right product of below reaction
SN r e a c t i o n
2. Discuss reactions of n-butyl bromide with CH3CH2O-Na+
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13. SN r e a c t i o n
1
Kinetics
Experiment_1
- Rxn of methyl bromide with NaOH in aq. ethanol solvent.
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14. SN r e a c t i o n
1
Kinetics
Experiment_2
- Rxn of tert-butyl bromide with NaOH in aq. ethanol solvent.
Observation
Conclusion
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15. SN r e a c t i o n
1
Order of reactivity of RX
Experiments
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16. SN r e a c t i o n
1
Order of reactivity of RX
- Relation btwn RX and mechanisms
Order of
react iv ity
of RX is…
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17. SN r e a c t i o n
1
SN2 : mechanism
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18. SN r e a c t i o n
1
SN2 : mechanism
Collision btwn substrates  Nu. attacks from back side.
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19. SN r e a c t i o n
1
SN2 : Stereochemistry
- Nu. attacks from back side 
 “back-side displacement,”
- E.g.
SN2
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complete inversion of configuration

20. SN r e a c t i o n
2
SN2 : Stereochemistry
Explaining mechanism with ball-stick model
(+) isomer of
reactant
(-) isomer of
product
back-side displacement
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21. SN r e a c t i o n
2
SN1 : mechanism
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22. SN r e a c t i o n
2
SN1 : mechanism
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23. SN r e a c t i o n
2
SN1 : Stereochemistry
- Nu. attacks from either side, back side or front side in step_2. so
racemic mixture may obtained as pdct.
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24. SN r e a c t i o n
2
SN1 : Stereochemistry
- But practically prdcts obtained with
of configuration.
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25. SN r e a c t i o n
2
SN1 : Stereochemistry
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26. SN r e a c t i o n
2
SN1 : Stereochemistry
I. After covalent bond breaking – initially both ions must be closed
together. (intimate pair)
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27. SN r e a c t i o n
2
SN1 : Stereochemistry
- Nu. can attack at all three conditions I, II & III.
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28. SN r e a c t i o n
rearrangement of carbocations:
- Stabilization of C+ intermediate.
- E.g.
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2
Explain Possible mechanisms
now

29. SN r e a c t i o n
rearrangement of carbocations:
Stability of Carbocation: 3o > 2o > 1o
Relative stability of 3o C+ favors rearrangement
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30. SN r e a c t i o n
Factor affecting SN reactions :
The Leaving Group
- In both SN reaction leaving group dissociates in Ts. It affects to the
reaction rate.
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C-X bond strength

31. SN r e a c t i o n
Factor affecting SN reactions :
The Nucleophile
- In SN2 rxn…
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32. SN r e a c t i o n
Factor affecting SN reactions :
The Nucleophile
- In SN1 rxn…
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33. SN r e a c t i o n
Factor affecting SN reactions :
Solvents
- Polar solvents like methanol and water stabilizes (decrease internal
energy) to charge species by intermolecular electrostatic intraction.
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34. SN r e a c t i o n
Factor affecting SN reactions :
Solvents
In SN1
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35. SN r e a c t i o n
Factor affecting SN reactions :
Solvents
In SN1
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36. SN r e a c t i o n
Factor affecting SN reactions :
Solvents
In SN1
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37. SN r e a c t i o n
Factor affecting SN reactions :
Solvents
In SN2
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38. 2018
3
SN r e a c t i o n

39. SN r e a c t i o n
SN1 vs SN2 :
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40. SN r e a c t i o n
SN1 vs SN2 :
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41. SN r e a c t i o n
SN1 vs SN2 :
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42. Structure and Uses
Structure and Uses
1. Ethyl chloride
- Refrigerating agent
- In manufacturing of Tetraethyllead [is a highly toxic compound used
as a gasoline additive.]
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43. Structure and Uses
Structure and Uses
2. Chloroform
- Used as laboratory solvent. It was previously used as an anesthetic.
3. Dichloromethane
- Used as laboratory solvent.
- As mobile phase in chromatography
- As organic phase in liquid-liquid extractions with separating funnel.
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44. Structure and Uses
Structure and Uses
4. Tetrachloromethane
- Refrigerating agent
- As propellant in aerosol sprayers
5. Iodoform
- used as an antiseptic agent for minor skin diseases.
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45. of the topic
End
Reference:
Organic Chemistry– Morrison & boyd
Textbook of org. chem. – Bahl & Bahl
Organic Chemistry – Francis A. Carey
Organic Chemistry – Paula Bruice