The Macroscale Synthesis of 1-Bromobutane from 1-Butanol by an Sn2 Reaction

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grams = 12.8 grams

Molar Mass = 12.8 g / 98.08 moles H2SO4 Molar Mass = .131 mol H2SO4 (3 sig figs)According to the above calculations 1-Butanol is the Limiting Reagent

Experimental Set-up

100 mL round bottom flask, tar scale,, 10 mL min. graduated Cylinder, Large Beaker to make an ice bath, Electric Flask Heater, Clamp for flask, ring stand, short refluxing condenser for reflux condensation, tubing for water, drain for water, water valve, temperature fitted so it's hoovering just above the liquid in the flask, stop watch, still-head, bent adapter attached to condenser for simple distillation, 50 mL Erlenmeyer Flask, small test tube to test the distillate for complete distillation, separator funnel, clean flask, 2nd Ice bath for cooling sulfuric acid, clean flask for separation of the next layer, 3rd clean collecting flask, 1 gram anhydrous calcium chloride pellets, 25 mL clean flask, boiling stone, collect final product in temperature between 99-103 degrees C, narrow mouth bottle of appropriate size, neatly made label with your name/ your partners name/ formula of final product and the name of the final product making sure that the label is neat and easy to read and place it securely to the container of final product.Safety Issues / Notes:

- ensure PPE (personal protective equipment) is worn at all times, inspect throughout the lab

- H2SO4 needs to be carefully handed. We are using a high molar concentration. As a strong oxidizer and base which make it corrosive and a danger to exposed tissue such as the lungs.

- 1-Bromobutane and 1-Butanol are very flammable .

- To prevent an uncontrolled reaction and danger from a very exothermic reaction ensure when using concentrated H2SO4 is done very slowly, under vented hood in ice bath to prevent unwanted competing reactions and to avoid heavy fumes and heat from highly corrosive H2SO4

Table of Physical and Chemical Properties

Reagent: Name

structure and formula

Molar mass(g/mol)

Density

(g/cm3)

Volume

Used (mL)

Molar Concentration

Grams

used

Melting Point

degree C

Boiling Point

degree C

Appearance at S.T.P

Sodium Bromide Na+Br-

102.89

3.21

13.3154

797

1396

White Crystalline solid

Sulfuric Acid H2SO4

HO

|

O= S = O

|

HO

98.08

1.84

11.5

10

10

337

Colorless to slightly yellow liquid

1-Bromobutane C4H9Br/\/\Br CH3CH2CH2CH2Br

137.02

1.2676

-1125

102

Clear colorless liquid

1-Butanol /\/\OH CH3(CH2)3OH

74.12

.81

10

-89.8

117.7

Colorless Liquid

H2O H/O\H Water

18.015

1

15

10

0

100

Colorless Liquid

Acetone (CH3)2CO O=

58.08

.7857

-95

56

Colorless Liquid

Sodium Hydroxide Na+OH-

39.997

1.11

10

3

318

1,388

Colorless Liquid

2-Butene CHH8 /\=/\

56.10

.64 Cis

.62 Trans

-138.9 Cis

-105.5 Trans

-9 Cis

3.75 Trans

White Solid

1-Butene C4H8 /\/=\

56.10

.62

-185

-6.3

Colorless Gas

Anhydrous Calcium Chloride CaCl2

110.98

2.15

772