Aleks Glod

TA: Lauren Pepi

CHEM 2211L
April 6, 2017
Nucleophilic Substitution
I.Introduction: No new techniques will be utilized in this lab, the lab generally involves reagent
mixing and observation. It is divided into three sections, these sections differently test a part of
nucleophilic substitution. In the first part will investigate SN1 conditions and their effect on
substrate substitution and leaving group identity. The second part also tests substrate substitution
and leaving group identity but under SN2 conditions. In the last part of the experiment the
solvent polaritys effect on SN1 reactions is determined. SN1 is a unimolecular substitution
while SN2 is bimolecular. SN1 has two steps, a rate determining initial step forms a carbocation
intermediate. In the second step, which is a fast step the nucleophile forms a bond with thee
reactive carbocation resulting in a stable product.
II.Procedure:
Part One: Unimolecular, Nucleophilic Subsitution (SN1) Conditions
1. Arrange 4 test tubes in a test tube stand, labeling 1-4 to avoid any mixups.
2. Test tubes 1-4 will contain the following compounds in the given order : 1) Bromo-2-
methylpropane 2) 2-bromobutane 3)1-bromobutane 4) 1-chlorobutane each containing .25mL
which is about 5 drops.
3. After organizing tubes obtain 4ML of 1% silver nitrate solution in ethanol from fume hood in a
10ml graduated cylinder. Record exact time the first drop was added in lab notebook
4. Next, add about 1 ml of the AgNO3 into each , this is about 20 drops. Once added, cover and
shake each tube to ensure mixing.
5. Watch for any cloudiness forming and record the exact time this happens. Also watch for the
precipitation of silver halide and record that time.
6. Tubes 1-3 offer a comparison of alkyl halide structure effects as related to SN1 reaction
conditions. Tubes 3 and 4 compare the effect of two different leaving groups under SN1 reaction
conditions.
7. After recording data, use small volume of acetone to clean each tube. Dispose in fume hood.
Part Two: Bimolecular, Nucleophilic Substitution (SN2) Conditions
8. Arrange the test tubes just as in step 1.
9. This time 4 ml of 15% sodium iodide solution in acetone are used.
10. Add 1 ml drop to each of the following tubes.
11. Record observations looking for any cloudy appearance, record the exact time is occurs. Also
watch for a sodium halide precipitate formation and record that time as well.
12. Tubes 1-3 offer a comparison of alkyl halide structure effects as related to SN2 conditions.
Tubes 3 and 4 compare the effects of two different leaving groups under SN2 conditions.
13. Clean the tubes out using a small amount of acetone and dispose of in the fume hood.
Part Three: Solvent Effects on Unimolecular, Nucleophilic Substitution SN1
14. Arrange 4 test tubes in stand. These will contain 1) 1 ml of 1;1 methanol to water solvent
solution . 2) 1 ml of 1:1 ratio of ethanol to water. 3) 1 ml of 1:1 ratio of 1-propanol to water
solvent solution. 4) 1 ml of 1:1 ratio of acetone to water solvent solution.
15. Add 3 drops of 0.5 NaOH and 3 drops of 1% phenolphthalein solution.
16. Finally add 3 drops of the 2-bromo-2-methylpropane to each test tube.
17, Record the exact time the first drop was added to each tube.
18. Once the proper alkyl halide has been added, cover and shake each tube to ensure proper
mixing of the reagents. Watch for pink coloration and record that exact time of reaction.
19. Record your data in tables similar to the ones found in the lab manual for each of the three
parts.
III.Safety:
Safety glasses and lab gloves must be worn at all times. Make sure your snorkels are
turned on at all times.
Ethanol, methanol, acetone , and 1-propanol are highly flammable so avoid hot surfaces,
sparks and flames.
The alkyl halide products formed in this reaction are volatile and highly toxic, potentially
mutagenic.
Sodium hydroxide is caustic and causes severe burns if it comes in contact with eyes or
skin.
Reagent Safety:
2-Bromo-2-Methylpropane
2-Bromobutane
1-Bromobutane
1-Chlorobutane
AgNO3
NaI
Sodium Hydroxide
 Phenolphthalein
Methanol
Ethanol
Water
Acetone
1-Propanol
IV.Table of Reagents:
Name of Compound Structure Molecular Weight Boiling point Density
2-Bromo-2-
methylpropane

2-Bromobutane

1-Bromobutane

1-Chlorobutane

AgNO3

NaI

Sodium Hydroxide

Phenolphthalein

Methanol

Ethanol
Water

Acetone

1-Propanol
Citations
"The PubChem Project." National Center for Biotechnology Information. PubChem Compound
Database. U.S. National Library of Medicine, n.d. Web. 25 Mar. 2017.
"Search ChemSpider." ChemSpider | Search and share chemistry. N.p., n.d. Web. 25 Mar. 2017.
Richard Hubbard, and Richard Morrison. " Nucleophilic Substitution
Modern Organic Chemistry I. N.p.: Worth, n.d. 1. Print.