Synthesis of tertiary alcohol using

benzyl chloride and acetone

Aim
To synthesize a tertiary alcohol using benzyl chloride and acetone through Grignard reaction.
Objectives
 To prepare a Grignard reagent from benzyl chloride and dry magnesium in the
presence of dry ether.
 To synthesize a tertiary alcohol from benzyl chloride and acetone.
 To separate the organic and aqueous layer using solvent extraction.
 Calculate percentage yield and obtain IR spectrum of the final product.
Reaction equations
1. Formation of grignard reagent

2. Formation of Alkoxide

3. Formation of tertiary alcohol

Sources
1. Peltzer, Raphael Mathias, et al. ‘The Grignard Reaction – Unraveling a Chemical
Puzzle’. Journal of the American Chemical Society, vol. 142, no. 6, Feb. 2020, pp. 2984–
94.
2. Bouzidi, Naoual, and Christel Gozzi. ‘Experimental Design and Optimization: Application
to a Grignard Reaction’. Journal of Chemical Education, vol. 85, no. 11, Nov. 2008, p.
1544.
3. Garst, John F., and Manuel P. Soriaga. ‘Grignard Reagent Formation’. Coordination
Chemistry Reviews, vol. 248, no. 7–8, Apr. 2004, pp. 623–52
4. King, R. Bruce. ‘Modern Aspects of Organometallic Chemistry’. Coordination Chemistry
Reviews, vol. 248, no. 7–8, Apr. 2004, p. 533.

Table of physical properties and hazards

Chemical substances Physical properties
Dry magnesium Silver-white color, solid state
Dry ether Colourless liquid, sweetish
pungent
Acetone Colourless liquid, sweet fruity Highly flammable, causes
Benzyl chloride Colorless to pale yellow
Sulphuric acid Clear colorless liquid
Sodium bicarbonate White crystalline powder
iodine dark-gray/purple-black,
lustrous solid
Sodium sulphate White crystalline solid
Hazards
Reacts vigorously with acid
and water, fire hazard
Highly flammable, forms
explosives peroxides when
exposed, harmful if
swallowed or inhaled
irritation
Corrosive to skin, eyes, and
respiratory tract, may cause
lung damage
Causes severe burns to skin
and eyes, reacts violently
with water
At high concentrations, it
may cause skin and eye
irritations when exposed.
Harmful if swallowed,
inhaled, or absorbed through
the skin, may cause irritation
to eyes and respiratory tract
May cause irritation to eyes
and skin
Preliminary calculations
1. Mass of benzyl chloride
NxMm= (0.14 mol)(126.58g/mol) = 17.7 g
V= m/d = 17.7g/ 1.11g/cm3 = 16.11 cm3

2. 10% m/v NaHCO3

m/v = mass of solute/ mass of volume
mass of solute = (10/100)(40ml)= 4.0 g

3. Theoretical yield
17.72 𝑔×150.22 𝑔/𝑚𝑜𝑙
theoretical yield = 126.58 𝑔/𝑚𝑜𝑙
= 21.03 g

Observations
Procedure Observations
Adding Mg, dry ether, and a grain of iodine in
the reaction flask with a magnetic follower.

Adding 10ml of benzyl chloride and ether

mixture to the reaction flask from the dropping
funnel.

Adding a mix of 10ml Acetone and 50ml dry

ether into the reaction flask.

Adding H2SO4 mix into the reaction flask.

Separating the aqueous layer from the
organic layer through extraction.

Drying the ether solution over anhydrous

sodium sulphate and heating the mixture.