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Alkyl Halides: Structure and Reactivity in Nucleophilic Subs

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rachelle cruz

on 2 December 2013

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Transcript of Alkyl Halides: Structure and Reactivity in Nucleophilic Subs

Alkyl Halides: Structure and Reactivity in Nucleophilic Substitutions
Part B Materials
7 test tubes
Test tube rack
10ml graduated cylinder
2% ethanolic silver nitrate solution
Organic chlorides:
1-chlorobutane
2-chlorobutane
2-chloro-2-methylpropane
3-chloropropene (allyl chloride)
Benzyl chloride
Chlorobenzene
Safety goggles
Stopwatch

Conclusion
To test SN1 reactions:
Treat each alkyl halides with silver nitrate in ethanol .
Result:
2-Methyl-2-propyl( 3°) precipitated rapidly.

Reactivity
To test SN2 reactions:
Treat each alkyl halides
with sodium iodine in
acetone.
Result:
All primary alkyl
halides precipitated
rapidly.

Tertiary alkyl halides
undergo SN1 reactions
since it reacts rapidly
when treated with silver
nitrate in ethanol.

Primary alkyl halides
undergo SN2 reactions
since it reacts rapidly when
treated with sodium iodine
in acetone.

Results
Reactivity of Halides Toward
Silver Nitrate and Sodium Iodide

Rachelle Cruz
Jacqueline Gjidoda
Roxanne Henry
Winey Yuen
The End
Presented by:
What are Alkyl Halides?
An Alkyl Halide is an organic compound in which halogen atoms have been substituted for hydrogen atoms of an alkane.
This reaction occurs by one of two mechanisms;

SN1
or
SN2
depending on the structure of the R group.
Classification is based on the carbon atom to which the halogen is directly attached:

Part B:
Reactivity of Halides toward Silver Nitrate
In this experiment, we tested the reactivity of several alkyl halides in an SN1 reaction using Silver ion with:
1-chlorobutane
,
2-chlorobutane
,
2 chloro-2methylpropane
,
allyl chloride
,
benzyl chloride
and
chlorobenzene
.
Alkyl chlorides yield a discernable silver chloride precipitate, which should be insoluable in ethanol, proving that a reaction occured.
Part C:
Reactivity of Halides toward Sodium Iodide
In this experiment we tested the reactivity of alkyl halides in an SN2 reaction with Iodine Ion as it is an effective nucleophile in SN2 displacement.
Using:
I-bromobutane
,
2-bromobutane
,
2-bromo-2-methylpropane
,
allyl bromide
,
benzyl bromide
and
bromobenzene

If reaction occurs, a precipitate of sodium chloride or sodium bromide will form.
Part B Procedure
1.Set up all seven clean and dry test tubes in the rack.
2.For each test tube:
Measure 2 ml of the 2% ethanolic silver nitrate solution in a 10 ml graduated cylinder and pour into tube.
3.Leave 1 tube to the side with only the ethanol solution in order to be used as a comparison.

Add 2 drops of one organic chloride to one test tube and repeat for the next five organic chlorides in their designated test tubes as well.
Shake each solution and with a stopwatch. Record the amount of time required for a silver chloride precipitate to form.

Part B Procedure
7 test tubes
Test tube rack
10ml graduated cylinder
15% solution of sodium iodide in anhydrous acetone
Organic bromides:
1-bromobutane
2-bromobutane
2-bromo-2-methylpropane
3-bromopropene (allyl bromide)
Benzyl bromide
Bromobenzene
Safety goggles
Stopwatch

Part C Materials
1. Set up all seven clean and dry test tubes in the rack.
2. For each test tube:
Measure 2 ml of a solution of 15% sodium iodide in anhydrous acetone in a 10 ml graduated cylinder and pour into tube.
3. Leave 1 tube with only the sodium iodide-acetone solution in order to be used as a comparison.

Part C Procedure
Add 2 drops of one organic bromide to one test tube and repeat for the next five organic bromides in their designated test tubes as well.
Mix the contents of each test tube and with a stopwatch. Record the amount of time required for a precipitate to form.

Part C Procedure
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