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Date:
Katheryn Soto
Partners
10/20/15
Drawer No.
Course / Section
#21
CHEM
315/204
Purpose:
The purpose of this experiment is to synthesize t-pentyl chloride by reacting t-butyl (t-pentyl) alcohol with
hydrochloric acid in an SN1 nucleophilic substitution reaction.
Experiment:
Date:
Partners
10/20/15
Drawer No.
Course / Section
#21
CHEM
315/204
Katheryn Soto
Approach:
Determine the mass of t-pentyl alcohol by weighing. Calculate the mass of HCl from the volume, density,
and %Composition. Calculate the moles of t-pentyl alcohol and HCl used. Determine the balanced
stoichiometric equation for the synthesis reaction. Determine the limiting reagent in the reaction based on
the moles of products used. Calculate the theoretical yield. Mix the reagents to initiate the reaction.
Isolate and purify t-pentyl chloride product by liquid/liquid extraction with H2O and Sodium Bicarbonate
to wash and separate the organic layer from the aqueous layer. Dry the product using Anhydrous sodium
sulfate. Determine the mass of the product by weighing. Compute the percent yield for the synthesis.
Determine the refractive index using the Abbe Refractometer. Correct the refractive index using the
temperature correction factor. Obtain the IR spectrum for the product.
References
Text
Pavia, D.L., Lampman, G.M., Kriz, G.S., Engel, .G.R., 2011, Introduction to Organic Laboratory
Techniques, A Small Scale Approach, GMU Edition, Chem 315/318, Cengage Learning: pp. 681708; pp.172-174
Slayden, S., Stalick, W., Roth, R, 2014, Organic Chemistry Laboratory Manual, 2nd Edition:
Pearson Custom Publishing: pp. 63-65
Web Site URL
Dr Schornicks Website: http:/mason.gmu.edu/~jschorni/tbutylchloride
Unknown or Synthesized Compound
2-Chloro-2-methylbutane (t-pentyl chloride), 594-36-5, CRC Handbook of Chemistry & Physics,
84th Edition, Lide, D.R., Editor-in-chief, 2003-2004, CRC Press, p 3-110, 2112.
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 1
Mass Alcohol
Results
Materials
T-Pentyl Alcohol
Equipment
in vial
Electronic
balance (0.001)
Calculator
Desc:
Equation Setup:
Mass of vial and sample (g) mass of empty vial(g)
= mass of alcohol sample (g)
Drawer No.
Course / Section
#21
CHEM
315/204
Unk No.
10.926
15.308
4.382g
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 2
Mass HCl
Approx. 25mL
HCl (37.3%)
Equipment
Graduated
cylinder (0.1)
Calculator
Desc:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
Equation Setup:
vol (mL) * density (g/mL) * %comp. (37.3) = mass
HCl
Mass HCl
Vol HCl (mL)
Density (g/mL)
% Composition
25.0mL
1.18g/mL
37.3%
25 * 1.18 * 0.373 =
11.004g
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 3
Moles of Reagents
HCl
Desc:
Equipment
Calculator
Equation Setup:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
4.382g
88.15g/mol
4.382 / 88.15 =
0.04971mol
Moles HCl
Mass (g)
M.W. (g/mol)
11.004g
36.47g/mol
11.004 / 36.47 =
0.3017mol
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 4
Drawer No.
Course / Section
#21
CHEM
315/204
1 : 1
Experiment:
Date:
10/20/15
Partners
Drawer No.
Course / Section
Katheryn Soto
#21
CHEM
315/204
Proc # 5
Results
Limiting Reagent
Materials
Equipment
Calculator
Desc:
Equation Setup:
t-pentyl alcohol + HCl t-pentyl chloride
Molar Ratio
Stoichiometric
Experimental
1:1
0.04971 : 0.3017
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 6
Theoretical Yield
#21
CHEM
315/204
Equipment
Calculator
Desc:
Course / Section
Results
Materials
Drawer No.
Equation Setup:
Where L.R = limiting reagent and M.W =molecular
weight:
Theoretical Yeild
t-pentyl alcohol (mol)
t-pentyl chloride (mol)
M.W. C5H11Cl (g/mol)
M.W. H2O
0.04971 * 106.59 * (1) =
0.04971 * 18.02 * (1) =
0.04971mol
1
106.59g/mol
18.02g/mol
5.298 g
C5H11Cl
0.8958 g
H2O
Experiment:
Date:
10/20/15
Partners
Drawer No.
Course / Section
#21
CHEM
315/204
Katheryn Soto
Proc # 7
Results
Desc:
Balanced
Equation
Molecular
Weight
Mass
(grams)
Moles
1 t-pentyl alcohol
+ 1 HCl
1 t-pentyl chloride
+ 1 H2O
88.15 g/mol
36.47g/mol
106.59g/mol
18.02g/mol
4.382 g
11.004 g
5.298 g
0.8958 g
0.04971 mol
0.3017 mol
0.04971 mol
0.04971 mol
Experiment:
Date:
Partners
Katheryn Soto
Proc # 8
Mix reagents
25 mL HCl
t-pentyl alcohol
in vial
Equipment
125 mL
sepratory funnel
Glass
funnel
Desc:
Equation Setup:
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Materials
10/20/15
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 9
Liquid-Liquid Extraction
Materials
Glass
funnel
Iron ring
Ring stand
125mL
sepratory funnel
Graduated
cylinder
150mL
beaker
Desc:
Course / Section
#21
CHEM
315/204
Results
Equipment
Drawer No.
Observations:
Experiment:
Date:
Katheryn Soto
Equation Setup:
Partners
10/20/15
Drawer No.
Course / Section
#21
CHEM
315/204
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 10
Dry Product
Anhydrous
sodium sulfate
t-pentyl chloride
product
Equipment
150mL
beaker
50mL
beaker
Desc:
Equation Setup:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
Observations:
Experiment:
Date:
Partners
Katheryn Soto
Proc # 11
Mass/Moles Product
Materials
Dried t-pentyl
chloride product
Drawer No.
Course / Section
#21
CHEM
315/204
Results
Equipment
10/20/15
Calculator
Electronic
balance (0.001)
50mL
beaker
Desc:
Experiment:
Date:
10/20/15
Partners
Drawer No.
Course / Section
#21
CHEM
315/204
Katheryn Soto
Proc # 12
Percent Yield
Results
Materials
Equipment
Calculator
Desc:
Percent Yeild
Experimental Yield
Theoretical Yield
(5.202 / 5.298) * 100 =
5.202g
5.298g
98.19%
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 13
Refractive index
t-pentyl chloride
product
Tissue
Alcohol
Dropper
Equipment
Abbe
refractometer (
0.0002)
Desc:
Equation Setup:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
Unk No.
1.4055
1.4054
1.4055
RI 23
Experiment:
Date:
10/20/15
Partners
Drawer No.
Course / Section
#21
CHEM
315/204
Katheryn Soto
Proc # 14
Materials
Equipment
Calculator
Desc:
Equation Setup:
Refractive Index (n) the ratio of the velocity of
light in the air to the velocity of light in the medium
being measured (Pavia, pp845)
For temperatures >20oC add the temperature
correction factor
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
Where N represents the refractive index reading.
The superscript indicates the temperature at which
the measurement was read. The subscript indicates
the light source utilized.
Results
Room temp = 20.5oC
t-butyl (t-pentyl) chloride
ND20 = NDRm Temp + (Room Temp - 20)* 0.00045
ND20 = 1.4055 +(20.5-20) * 0.00045
ND20 = 1.4057
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Proc # 15
IR Spectroscopy
2 NaCl plates
(salt plate
t-pentyl chloride
product
Acetone
KBR (potassium
bromide) pellet
chemwipe
Desc:
Equipment
IR
Spectrometer
Equation Setup:
Course / Section
#21
CHEM
315/204
Results
Materials
Drawer No.
CH3 at 1375cm-1
CH2 at 1450cm-1
Experiment:
Date:
Katheryn Soto
Partners
10/20/15
Drawer No.
Course / Section
#21
CHEM
315/204
Summary of Results:
The mass of t-pentyl alcohol was 4.382g. The mass of HCl was 11.004g. The moles of t-pentyl
alcohol used were 0.04971mol. The moles of HCl used were 0.3017mol. The stoichiometric molar ratio
of t-pentyl alcohol:HCl was 1:1. The experimental molar ratio of t-pentyl alcohol:HCl was
0.04971:0.3017. The experimental molar ratio of t-pentyl alcohol:HCl was less than that of the
stoichiometric molar ratio therefore t-pentyl alcohol was limiting, and only 0.04971 of the 0.317moles
of HCl was used in the reaction. The theoretical yield for the synthesis reaction was 5.298g t-pentyl
chloride and 0.8958g H2O. The mass of t-pentyl chloride synthesized was 5.202g. The percent yield for
the synthesis was 98.19%. The raw refractive index for the product was 1.4055. The corrected
refractive index value calculated was 1.405720. The IR spectrum obtained showed the following:
aliphatic (saturated) C-H stretch <3000cm-1, Cl at approx. 785cm-1, CH2-Cl bend wagging at approx.
1230cm-1, CH3 at 1375cm-1, and
CH2 at 1450cm-1.
Experiment:
Date:
Katheryn Soto
Partners
10/20/15
Drawer No.
Course / Section
#21
CHEM
315/204
Experiment:
Date:
10/20/15
Partners
Katheryn Soto
Drawer No.
Course / Section
#21
CHEM
315/204
594-36-5
2-Chloro-2methylbutane
t-pentyl chloride
Synonyms
Melting Point
(oC)
Lit -72.6oC
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Boiling Point
(oC)
Lit 85oC
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Lit sl H2O
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Density
Rel to Water
Lit 0.865320
Exp
Lit
Exp
Lit
Exp
Lit
Exp
Molecular
Formula
Structural
Formula
C5H11Cl
Experiment:
Date:
Katheryn Soto
Partners
10/20/15
Drawer No.
Course / Section
#21
CHEM
315/204