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L Labs
L Labs
Nucleophilic Substitution of Alkyl Halides, Exp. 17A, B, and C, pages 187-192 in Taber
This week you will be doing examining real life SN1 and SN2 reactions to see first hand the
effects solvent, sterics (1, 2, or 3 substitution) and temperature have on reaction rates.
The concepts are the same you learned in CH 8 of Carey. Im going to review those
concepts and then go into what you will do this week in lab, and what you should expect.
The Big Difference Between SN1 and SN2: Do You Get a Carbocation?
Although there is sometimes confusion about the differences between SN1 and SN2
reactions, you should know that they are essentially the same reaction: in both cases, the
carbon-leaving group bond is broken, and a carbon-nucleophile bond is formed.
Whats the difference then? Simple:
In an SN1 reaction a carbocation is formed: the LG takes off and then the Nu attacks.
In an SN2 reaction no carbocation is formed: the LG takes off as the Nu attacks.
All of the differences between SN1 and SN2 reactions stem from these two facts!
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On the other hand, in SN2 reactions the nucleophile attacks at the same time as the leaving
group leaves: a bond is being formed as a bond is being
broken.
So there is a lot of action going on around the carboncarbon normally has four bonds are it, but in this case five
bonds are around it. The carbon gets crowded.
So to because of crowding, SN2 reactions work best on the
least substituted alkyl halides: 1 is better than 2 which is better than 3.
The effects of crowding are also called steric effects (or just sterics for short).
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You will find that for SN2 n-butyl bromide and n-butyl chloride react right away. sec-Butyl
chloride and crotyl chloride will react after a few minutes, but youd be there all day waiting
for tert-butyl chloride to react.
For SN1 tert-butyl and crotyl chloride react the
fastest because they give the most stable
carbocations.
sec-Butyl chloride will react after a few minutes,
and the primary alkyl halides wont react at all.
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Exp. B - Solvents
In this experiment you will test the SN1 reaction rate of tert-butyl chloride with water in
different acetone-water solutions- 55:45 acetone-water, 60:40, 65:35, and 70:30.
Youll find that one of the middle ones (60:40 or 65:35) gives the fastest reaction rate.
Why in the middle? Because tert-butyl chloride is insoluble in water, but soluble in acetone,
so you need some acetone for the reaction to work. But since acetone is a polar aprotic
solvent, and SN1 requires a protic solvent, too much acetone is bad too.
Youre going to setup a test tube for each solvent mixture you will be testing (~4 test tubes).
In each tube add 2 mL of solvent, 3 drops of 0.5 M NaOH solution, and 1-2 drops of
phenolphthalein indicator.
Place the tubes in a water bath thats around 30 C.
Once the tubes are warm, add 3 drops tert-butyl chloride to each and measure how long it
takes for the reaction mixture to turn clear.
One of the solvent systems will turn clear in 5-10 minutes. This is the one you will use in
part C.
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Why did do you have to make a graph? Because the slope of this line is equal to the
activation energy divided by (2.3 x R). So you can now calculate the activation energy: