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Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

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:

Synthesis of T-Pentyl Chloride


Name

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:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Proc # 1

Mass Alcohol

Results

Materials
T-Pentyl Alcohol

Equipment

in vial

Electronic
balance (0.001)
Calculator

Desc:

Tare the balance


Record the mass of the vial containing
the alcohol to the precision limit of the balance.
Record the mass of the empty vial.
Calculate the mass of alcohol used.

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.

Mass t-pentyl alcohol


Mass vial
Mass vial + sample
Mass sample
15.308 - 10.926 =

10.926
15.308
4.382g

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

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.

Dispense approx. 25mL HCl into a


graduated cylinder.
Determine the mass of the sample using
the volume, density and % composition of the
solution.

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:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Proc # 3

Moles of Reagents

Pre weighed tpentyl alcohol


Pre weighed

HCl
Desc:

Equipment

Calculator

Calculate the moles of reagents using


their mass (g) and their molecular weights
(g/mol)

Equation Setup:

Course / Section

#21

CHEM
315/204

Results

Materials

Drawer No.

Moles t-butyl (t-pentyl) alcohol


Mass (g)
M.W. (g/mol)

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:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Proc # 4

Drawer No.

Course / Section

#21

CHEM
315/204

SN1 Nucleophilic Substitution reaction t-pentyl chloride

Stoichiometric Balanced Equation

1mol C5H12O + 1mol HCl 1mol C5H11Cl + 1mol H2O


Molar Ratio

1 mol C5H12O + 1 mol HCl


Reaction Mechanism

1 : 1

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Drawer No.

Course / Section

Katheryn Soto

#21

CHEM
315/204

Proc # 5

Results

Limiting Reagent
Materials

Equipment

Calculator

Desc:

Compare the stoichiometric molar ratio of


reactants for the synthesis of t-butyl (t-pentyl)
chloride to the experimental moles of reactants
If the stoichiometric molar ratio is greater
than the experimental molar ratio, the reactant in
the numerator is limiting
The limiting reagent determines the
maximum quantity of product that can be
produced in a chemical reaction.

Equation Setup:
t-pentyl alcohol + HCl t-pentyl chloride

Molar Ratio
Stoichiometric
Experimental

1:1
0.04971 : 0.3017

0.04971 / 0.3017 = 0.1648


Observations:

0.1648 < 1 (Experimental ratio <


Stoichiometric ratio) t-butyl (t-pentyl)
alcohol is the limiting reagent

Only 0.04971 mol of the 0.3017 mol of


HCl is needed to react with the 0.04971 mol
of t-pentyl alcohol used

0.2519 mol of HCl are in excess

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Proc # 6

Theoretical Yield

#21

CHEM
315/204

Equipment

Calculator

Desc:

Course / Section

Results

Materials

Drawer No.

Determine the maximum product possible


based on the stoichiometry of the reaction, the
moles of reactants available, and the limiting
reagent.

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:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Drawer No.

Course / Section

#21

CHEM
315/204

Katheryn Soto

Proc # 7

Theoretical Yield Summary Table

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:

Synthesis of T-Pentyl Chloride


Name

Partners

Katheryn Soto

Proc # 8

Mix reagents

25 mL HCl
t-pentyl alcohol

in vial

Equipment

125 mL
sepratory funnel
Glass
funnel

Desc:

Transfer sample to a clean dry 125 mL


sepratory funnel using a glass funnel
Add pre measured HCl to the sepratory
funnel

Equation Setup:

Drawer No.

Course / Section

#21

CHEM
315/204

Results

Materials

10/20/15

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Proc # 9

Liquid-Liquid Extraction
Materials

Pre weighed tpentyl Alcohol in vial


Pre measured
HCl
10mL H2O
20mL 5%
NaHCO3(aq)

Glass
funnel

Iron ring
Ring stand
125mL
sepratory funnel
Graduated
cylinder
150mL
beaker

Desc:

Course / Section

#21

CHEM
315/204

Results

Equipment

Drawer No.

Assemble iron ring, ring stand and


funnel.
Transfer the alcohol to a 125mL
sepratory funnel.
Add approx. 25mL of HCl to the
sepratory funnel
Stopper the funnel and swirl the mixture
gently for 1 minute.
Invert the funnel and release the pressure
slowly turning the stopcock.
Close the stopcock and repeat this
process 3-4 times.
Allow to settle and drain the aqueous
layer into a large beaker.
Repeat this process until the amount of
gas is minimized.
Add 10mL of 5% Sodium bicarbonate
(aq), swirl and vent.
Allow to settle and drain the aqueous
layer into the waste container.
Repeat process with a second 10mL
portion of NaHCO3(aq).
Repeat process with 10mL distilled H2O.
Decant product remaining in sepratory
flask into a clean, dry 150mL beaker.

Observations:

Because HCl is denser than C5H11Cl, in


this extraction, the aqueous layer is at the base
of the sepratory funnel and the organic layer
remains in the sepratory funnel.

Top layer of liquid (C5H11Cl and H2O)


was cloudy in appearance

The bottom layer (HCl) was clear in


appearance

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

Katheryn Soto
Equation Setup:

Partners

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Proc # 10

Dry Product

Anhydrous
sodium sulfate
t-pentyl chloride
product

Equipment
150mL

beaker
50mL

beaker

Desc:

Add Anhydrous Sodium Sulfate to the


crude product
Swirl gently until the product turns clear
Decant the liquid solution carefully from
the sodium sulfate into a clean, dry 50mL
beaker

Equation Setup:

Course / Section

#21

CHEM
315/204

Results

Materials

Drawer No.

Observations:

The C5H11Cl product had a cloudy


appearance.

After addition of anhydrous sodium


sulfate, the product went from cloudy to clear

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

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:

Tare the balance

Place a clean, dry 50mL beaker on the


electronic balance

Record the mass of the 50mL beaker

Transfer the dried product to the beaker

Record the mass of the product


Equation Setup:
Mass of beaker and sample (g) mass of empty
beaker(g) = mass of product(g)

Mass t-pentyl chloride


Mass beaker
30.122
beaker + product
35.324
Mass product
35.324 30.122 = 5.202g

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Drawer No.

Course / Section

#21

CHEM
315/204

Katheryn Soto

Proc # 12

Percent Yield

Results

Materials

Equipment

Calculator

Desc:

Provides a measure of efficiency for the


reaction by comparing the ratio of the actual
and the theoretically expected product yields
Equation Setup:

Percent Yeild
Experimental Yield
Theoretical Yield
(5.202 / 5.298) * 100 =

5.202g
5.298g
98.19%

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Proc # 13

Refractive index

t-pentyl chloride
product
Tissue
Alcohol
Dropper

Equipment

Abbe
refractometer (
0.0002)

Desc:

Note and record the temperature of the


room
Carefully clean the prisms of the Abbe
refractometer with a tissue moistened with
alcohol.
Add a small amount of the compound
between the prisms.
Gently close the prisms.
Flip the switch on the left of the
instrument up to turn on the Sodium-D lamp
and adjust it into position.
Use the adjustment knob at the right of
the instrument so the crosshairs intersect with
the horizontal dividing line of the visual field.
Adjust the drum knob at the front of the
instrument to sharpen the horizontal line if
chromatic aberration occurs.
Press down on the switch on the left of
the instrument to display the refractive index
scale
Read and record the refractive index to
four decimal places.
Repeat this measurement and record a
second reading.

Equation Setup:

Course / Section

#21

CHEM
315/204

Results

Materials

Drawer No.

Unk No.

Room temperature: 20.5oC


t-pentyl chloride
1st ND
2nd ND
Avg ND:

1.4055
1.4054
1.4055

RI 23

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Drawer No.

Course / Section

#21

CHEM
315/204

Katheryn Soto

Proc # 14

Temperature Correction Factor

Materials

Equipment

Calculator

Desc:

Adjusts the measured value of the


refractive index (ND) obtained using the Abbe
refractometer to standard temperature of 20oC.
Refractive index is both wavelength and
temperature dependent for a given compound.
Temperature and density are inversely
related.
Density and the velocity of light are
inversely related.
As temperature increases, density
decreases and velocity of light increases.
Refractive index decreases as
temperature increases.

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:

Synthesis of T-Pentyl Chloride


Name

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

Place 1-2 drops of sample between 2 salt


plates

Place salt plate sandwich in plate holder


and inset into beam slot of the IR Spectrometer.
Check with professor to make sure
background has been scanned.
Select appropriate memory location (X,
Y, or Z)
Press scan button. Make sure the
number of scans indicates 4.
Press execute button.
If absorption does not read properly,
remove salt plate and try again using a smaller
amount of the unknown sample.
Run and record a second trial
Press plot button to produce graph.
Remove cell holder and disassemble the
apparatus.
Clean the salt plate with acetone and dry
with chem wipe
Place salt plates in desiccator to dry.

Equation Setup:

Course / Section

#21

CHEM
315/204

Results

Materials

Drawer No.

aliphatic (saturated) C-H stretch


<3000cm-1
Cl at approx. 785cm-1
CH2-Cl bend wagging at approx. 1230cm1

CH3 at 1375cm-1
CH2 at 1450cm-1

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

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:

Synthesis of T-Pentyl Chloride


Name

Katheryn Soto

Partners

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204

Analysis & Conclusions:


In the synthesis of t-pentyl chloride, the molar ratio of the reagents was 1:1. Because fewer moles of tpentyl alcohol were available based on the volumes and concentrations of the reagents
(HCl=0.3017mol; t-pentyl alcohol=0.04971mol) t-pentyl alcohol was the limiting reagent; as such, a
maximum product yield of 5.298g was anticipated. The actual yield of t-pentyl chloride was 5.202g,
representing 98% of the theoretical yeild.
It is difficult to isolate 100% yield with this compound because t-pentyl chloride is easily hydrolyzed by
water, and can quickly begin to convert back to the its starting product during the extraction process.
The refractive index was measured to verify the identity of the compound. After adjustment with the
temperature correction factor, the refractive index measured (1.405720) was reasonably close to the
literature value (1.405520). IR spectral analysis was performed as a final confirmation. Analysis of the
spectrum also verified the identity of the compound as t-pentyl chloride.
The IR showed that there was no aromaticity or unsaturation in the molecule (C-H stretch <3000cm -1)
The chlorine molecule was present at approx. 785cm-1 (the fingerprint region). Since the hydrocarbon
groups must be saturated there must be 5 carbons and 11 hydrogens present in the molecule. The
molecular formula is thus C5H11Cl.

Experiment:

Date:

Synthesis of T-Pentyl Chloride


Name

10/20/15

Partners

Katheryn Soto

Drawer No.

Course / Section

#21

CHEM
315/204

Literature Summary (Unknowns, Synthesized Compounds)


Unknown No.
CAS No.
Name (IUPAC)

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

Refractive Index Lit 1.405520


(nD20)
Exp 1.405720
Solubility
(Rel to Water)

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:

Synthesis of T-Pentyl Chloride


Name

Katheryn Soto

Partners

10/20/15
Drawer No.

Course / Section

#21

CHEM
315/204