Identification and

Synthesis of Compound V
CHEM 211
Dianna Chrysler, Jose Hernandez,
Sahar Raziq, Shayln Russell-Fritch
What do the 5 Senses Tell?
Sense of Taste

Sense of Touch

Sense of Hearing

Sense of Sight

Sense of Smell
Smells Volatile and of Alcohol
Purification Techniques
Step 1: Gravity Filter

● Heterogeneous mixture
● Mixture contains solid matter
 ● Homogenous mixture, but might
Purification Techniques contain another structure
Step 2: Distillation ● ???????
● Structures that contain alcohol have a
low boiling point
● Slowly raise the temperature until the
structure evaporates from the flask
Boiling Point at 117.9°C
● Structures have a particular boiling point
● ?????
 Properties and Purification
Smell: Volatile, alcohol

Boiling point: 117.9°C

Appearance: Colorless

Purification technique: Gravity filtration

and distillation
IR Theoretical Experimental

Wavenumber (cm-1) Peak Description Functional group

3300 Strong broad O-H alcohol

2800 Sharp, strong C-H alkane

 Theoretical
H-NMR
Chemical Shift Integration Splitting Group
(ppm)

3.626 2 triplet CH2-CH2

2.24 1 singlet OH

1.53 2 quintet CH2-CH2-CH2

1.39 2 sextet CH2-CH2-CH3

0.94 3 triplet CH3-CH2

Experimental
C-NMR Theoretical

Chemical Splitting Group

Shift (ppm)

62.30 triplet CH2

34.89 triplet CH2

19.09 triplet CH2

13.92 quartet CH3

 MS Theoretical

m/z M Intensity Fragment

74 M 0.1 CH3-CH2-CH2-CH2-OH

73 M-1 1 CH3-CH2-CH2-CH2-O

56 M-18 100 CH3-CH2-CH2-CH

41 M-33 68 CH3-CH2-C
 Identity and Structure

1-butanol
Summary: The IR spectra indicated the presence of an OH group and CH (alkane) groups. The C-NMR
showed that there were four different types of carbon groups, one CH3 and three CH2 groups. The H-
NMR confirmed this and revealed that the carbon groups were arranged in a chain with the OH group
on one end.
 Molecular Model

Ball-and-Stick Model Electrostatic Potential Map

Synthesis
 Cost Analysis
Material Cost (Sigma-Aldrich) Cost per Gram
Propane (99.5%) $348/145 g $2.40

Br2 (reagent grade) $161/500 g $0.32

Ethanol (99.5%) $123/L (789 g) $0.16

CCl4 (99.5%) $434/L (1590 g) $0.27

NaNH2 (98%) $153/1000 g $0.15

Isopropyl alcohol (99.7%) $169/8000 g $0.02

Borane THF solution $253/800 mL (718.4 g) $0.35

Hydrogen peroxide (30% by weight in water) $100/500 mL (~500 g = 150 g H2O2) $0.67 (per gram H2O2)

NaOH (reagent grade)) $173/2500 g $0.69

To prepare 100 g 1-butanol:
100 g 1-butanol x
mol/
74.12 g = 1.349 mol 1-butanol
Cost Analysis
Reagent Moles Required Molar Mass Mass Required Cost/gram Total Cost
Propane 1.349 44.1 g/mol 59.4909 g $2.40 $142.78

Br2 4.047 159.808 g/mol 646.743 g $0.32 $206.96

Ethanol 1.349 46.07 g/mol 62.148 g $0.16 $9.94

CCl4 1.349 153.82 g/mol 207.50 g $0.27 $56.03

NaNH2 5.396 39.01 g/mol 210.498 g $0.15 $31.57

Isopropyl alcohol 1.349 60.1 g/mol 81.085 g $0.02 $1.62

Borane THF 1.349 85.94 g/mol 115.933 g $0.35 $40.58

H2O2 1.349 34.01 g/mol 45.879 g $0.67 $30.74

NaOH 1.349 39.997 g/mol 53.956 $0.69 $37.23

 Cost Analysis

Material Cost (Sigma- Grams/liter Cost/gram Cost/100 g

Aldrich)
1-butanol (99%) $52.50/0.5 L 810 $0.13 $13
 Cost Analysis
Synthesis Cost Purchase Cost

$557.45/100 g $13/100 g