pls i need mechanisms for the 9 Alkyl halides. With 15% Nal-in Acetone SN2 with
ID: 1017251 • Letter: P
Question
pls i need mechanisms for the 9 Alkyl halides.
With 15% Nal-in Acetone SN2 with 1% Ethanolic silver Nitrate SN1
precipitate
50 °C water bath
precipitate
100 °C water bath
1. 2-chlorobutane
NO
NO PPT
No precipitate/cloudiness)
Yes(Cloudiness)
2. 2- bromobutane
NO
Cloudy after
Yes(Cloudiness)
3. 1-chlorobutane
NO
Cloudy after
No precipitate/cloudiness)
No precipitate
4. 1-bromobutane
Yes(immediately)
No precipitate/cloudiness)
Dense precipitate
5. 2-chloro-2-methylpropane
NO
NO PPT
Yes(Cloudiness)
6. Benzyl chloride
Yes(immediately)
Yes(Cloudiness)
7. Bromobenzene
NO
NO PPT
No precipitate/cloudiness)
No precipitate/cloudiness
8. Bromocyclohexane
NO
NO PPT
Yes(Cloudiness)
9. Bromocyclopentane
NO
Cloudy after
Yes (Dense precipitate)
9 Alkyl halides.
precipitate
50 °C water bath
precipitate
100 °C water bath
1. 2-chlorobutane
NO
NO PPT
No precipitate/cloudiness)
Yes(Cloudiness)
2. 2- bromobutane
NO
Cloudy after
Yes(Cloudiness)
3. 1-chlorobutane
NO
Cloudy after
No precipitate/cloudiness)
No precipitate
4. 1-bromobutane
Yes(immediately)
No precipitate/cloudiness)
Dense precipitate
5. 2-chloro-2-methylpropane
NO
NO PPT
Yes(Cloudiness)
6. Benzyl chloride
Yes(immediately)
Yes(Cloudiness)
7. Bromobenzene
NO
NO PPT
No precipitate/cloudiness)
No precipitate/cloudiness
8. Bromocyclohexane
NO
NO PPT
Yes(Cloudiness)
9. Bromocyclopentane
NO
Cloudy after
Yes (Dense precipitate)
Explanation / Answer
acetone is especially useful for potassium halides, I think potassium is better surrounded by acetone molecules than sodium ions. The reaction is called Finkelstein reaction and is basically an SN2 exchange. Acetone is the solvent . It dissolves all the reactants and sodium iodide, but other solvents can be used as well provided that it dissolves all the ingredients.
The mechanism is like this:
I(-) ......... R-X --> I-R + X(-)
In the reaction, iodide attacks the alkyl group backwards and as soon as iodide hits the alkyl group, the X is released and the configuration is reversed. This is called as Walden's reconfiguration. For example, an optically active compound like R will be converted to an S.
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