preparation of t-butyl chloride
DESCRIPTION
Preparation of t-butyl chloride. (2-chloro-2-methylpropane). (CH 3 ) 3 C OH + H Cl. Reaction Mechanism?. (CH 3 ) 3 C Cl + H 2 O. Leaving Group. (CH 3 ) 3 C OH + H - Cl. +. -. (CH 3 ) 3 C OH 2 + Cl. Cation. +. (CH 3 ) 3 C -OH 2. +. (CH 3 ) 3 C. H 2 O. - PowerPoint PPT PresentationTRANSCRIPT
![Page 1: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/1.jpg)
(2-chloro-2-methylpropane)
C
CH3
CH3
CH3
OHHCl
C
CH3
CH3
CH3
Cl + H2O
t-butyl alcohol t-butyl chloride
Preparation of t-butyl chloride
![Page 2: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/2.jpg)
(CH3)3COH + HCl
(CH3)3CCl + H2O
Reaction Mechanism?
![Page 3: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/3.jpg)
(CH3)3COH + H-Cl
(CH3)3COH2 + Cl + -
Leaving Group
![Page 4: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/4.jpg)
(CH3)3C-OH2 +
(CH3)3C + H2O
Cation
![Page 5: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/5.jpg)
(CH3)3C +
+ Cl-
(CH3)3CCl
Cation Adds Chloride
![Page 6: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/6.jpg)
+sp2 flat
p
tert-Butyl Cation
![Page 7: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/7.jpg)
Reaction Coordinate
![Page 8: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/8.jpg)
R .... OH2
+ +
Transition State
![Page 9: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/9.jpg)
Animation
![Page 10: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/10.jpg)
Substitution
Nucleophilic
1 bond at a time
SN1
![Page 11: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/11.jpg)
Increasing Stability
![Page 12: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/12.jpg)
Side Reaction
C
CH3
CH3
CH3
OHHCl
C
CH3
CH3
CH3
Cl + H2O
t-butyl alcohol t-butyl chloride
C
CH3
CH3
CH3
OHHCl
+ H2O
t-butyl alcohol
CH2C
CH3
CH3
isobutylene
Main Reaction
![Page 13: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/13.jpg)
CH2C
CH3
CH3
C
CH3
CH3CH3
C
CH3
CH3
CH3
Cl
SN1E1
![Page 14: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/14.jpg)
Shake t-BuOH with concentrated HCl
Separate layers
Wash saturated aqueous NaCl
Wash saturated aqueous NaHCO3
Dry
Distill
Procedure
![Page 15: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/15.jpg)
t-BuCl
Shake t-BuOH with HCl
![Page 16: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/16.jpg)
NaHCO3 + HCl
CO2 + H2O + NaCl
Wash to remove excess HCl
![Page 17: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/17.jpg)
Cool receiver
Distill product
![Page 18: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/18.jpg)
Clamp joints
![Page 19: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/19.jpg)
A + B CMW 100 100 200
Use: 10 g A 20 g B
Limiting Reagent
Theoretical Yield
Experimental Yield
Yield Calculations
![Page 20: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/20.jpg)
A + B CMW 100 100 200
Cpd Mass MW Moles
A 10 g 100 0.10
B 20 g 100 0.20
0.10 moles x 200 = 20 g
Experimental yield (%):100 x wt product / 20
LimitingReagent
Theoretical yield:
![Page 21: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/21.jpg)
CH3CH2CH2CH2OH
n-butyl alcohol
HBr
CH3CH2CH2CH2Br
n-butyl bromide
n-Butyl Alcohol + HBr
![Page 22: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/22.jpg)
RCH2OH + H+ RCH2OH2
+
C
R
HH
OH2Br
transition state
RCH2Br
Transition State
![Page 23: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/23.jpg)
Mechanism
![Page 24: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/24.jpg)
XCY
- -
CY X-XCY
-
Reaction Coordinate
Energy
TransitionState
![Page 25: Preparation of t-butyl chloride](https://reader033.vdocuments.mx/reader033/viewer/2022061419/568159c4550346895dc715c2/html5/thumbnails/25.jpg)
Substitution
Nucleophilic
2 bonds at a time
SN2