Ryan Gohman

Sayani Roy Chowdhury

2/16/2020

Acidic vs. Basic Conditions in the Nucleophilic Ring-opening of 1,2-Epoxyhexane: Pre lab

Introduction:
In this experiment, 1,2-epoxyhexane will undergo both an acid catalyzed ring opening,
and a base catalyzed ring opening. It will form two different products when done in basic and
acidic conditions. The acidic conditions include sulfuric acid in methanol. The methanol acts as
the nucleophile. In terms of regioselectivity in the acid catalyzed reaction, the nucleophile will
attack the more hindered carbon as seen in an SN1 reaction. In terms of stereospecificity, the
nucleophile will attack from the side of the molecule opposite the epoxide ring which is
characteristic of an SN1 reaction. The basic conditions include sodium methoxide in methanol.
The methoxide will substitute preferentially at the least hindered carbon position of the epoxide
ring. In terms of regioselectivity and stereospecificity, the base catalyzed ring opening functions
as a SN2 reaction.
In the base catalyzed reaction, the familiar technique of reflux is employed upon the
starting materials. In both reactions, liquid-liquid extraction is used in order to extract the
product. Furthermore, under both acidic and basic conditions, the solvent is decanted and
removed via rotovap. Finally, gas chromatography and IR spectra of the final products are
analyzed for comparison to spectra of the starting materials.

Balanced Equation and Mechanism:

Acidic Conditions Mechanism

Basic Conditions Mechanism

Acidic Conditions General Reaction

Basic Conditions General Reaction

Table of Reagents:

Name Structure MW (g/mol) BP/MP (C) Density

(kg/m^3)

1,2-epoxyhexane 100.161 BP: 117.1 831

Sulfuric acid 98.079 BP: 337 1840

Methanol 32.04 BP: 64.7 792

Diethyl ether 74.12 BP: 34.6 713

Sodium 84.007 MP: 50 2200

bicarbonate
 Magnesium 120.366 MP: 1124 2660
sulfate

Sodium 54.03 MP: 300 1300

methoxide

Ammonium 53.491 MP: 338 1530

chloride

Safety:

Name Safety/Precautions

1,2-epoxyhexane Highly flammable liquid and vapor. Causes

irritation to skin and serious
irritation to eyes. May cause irritation upon
inhalation

Sulfuric acid Very hazardous to skin and eyes, or upon

inhalation or ingestion. May cause
damage to mucous membranes of eyes,
mouth, and respiratory tract.
Carcinogenic. The substance may be toxic to
kidneys, lungs, heart,
cardiovascular system, upper respiratory
tract,eyes, teeth

Methanol May cause irritation to skin and eyes, or upon

inhalation or ingestion.
Mutagenic for mammalian somatic cells

Diethyl ether May cause irritation to skin and eyes, or upon

inhalation or ingestion.
Mutagenic for mammalian somatic cells. The
substance may be toxic to skin,
 central nervous system.

Sodium bicarbonate May cause irritation to skin and eyes, or upon

inhalation or ingestion.

Magnesium sulfate May cause irritation to skin and eyes, or upon

inhalation or ingestion.

Sodium methoxide May cause irritation to skin and eyes, or upon

inhalation or ingestion.Eye
contact can result in corneal damage or
blindness. Skin contact can produce
inflammation and blistering. Inhalation of
dust will produce irritation to
gastrointestinal or respiratory tract.

Ammonium Chloride May cause irritation to skin and eyes, or upon

inhalation or ingestion.May
cause irritation of the digestive tract. May
cause systemic toxicity with
acidosis.

Additional Safety Precautions:

Wear appropriate lab attire. Do not remove safety glasses or gloves at any time during the lab.
Take care to prevent spilling any compounds. Refrain from sealing the reflux apparatus air tight.
Rinse skin and eyes thoroughly if contact is made as these compounds can cause severe skin or
eye damage. In order to prevent the inhalation of toxic fumes, ensure that the snorkel at each
station is on and functioning properly. Diethyl ether is an extremely flammable compound. Be
sure to keep these substances away from open flames and hot surfaces. Dispose of all waste in
the designated waste container.
Procedure:

Partner A: Acidic Conditions

● 0.5 g of 1,2-epoxyhexane was placed into a microscale round bottom flask (14/10).
● The epoxide was dissolved by adding 5 mL methanol while being stirred with a stir bar.
● 1 drop of sulfuric acid was added to the solution and it was stirred for 30 minutes.
● The reaction was washed with 5 mL sodium bicarbonate solution in a 125 mL separatory
funnel.
● The product was extracted from the aqueous wash with two 10 mL portions of diethyl
ether.
● The ether layers were combined then dried the organic solution with magnesium sulfate.
● The liquid was decanted into a 50 mL round bottom flask.
● The organic extract was rotovapped with the flask immersed in room temperature water
until no change in mass was observed.
● Final mass of the product was recorded.

Partner B: Basic Conditions

● 0.4 g of sodium methoxide powder was obtained and placed into a microscale round
bottom flask (14/10) along with 5 mL of methanol and a spin vane.
● 0.5 g of 1,2-epoxyhexane was added to this mixture.
● It was refluxed for 30 minutes.
● The reaction mixture was washed with 5 mL of saturated ammonium chloride solution in
a 125 mL separatory funnel.
● The product was extracted from the aqueous wash with two 10 mL portions of diethyl
ether,
● The ether layers were combined then dried the organic solution with magnesium sulfate.
● The liquid was decanted into a 50 mL round bottom flask.
● The organic extract was rotovapped with the flask immersed in room temperature water
until no change in mass was observed.
● Final mass of the product was recorded.

GC Analysis: Both Partners

● A small vial was obtained from my TA and a solution consisting of one drop of my
product mixture to 2 mL of methanol was made.
● The GC of our product mixture was run.
● The product spectra of the GC was compared to the starting material.
● Product ratios were determined of each reaction.