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Synthesis and Chemistry of Alkenes

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Synthesis and Chemistry of Alkenes                                           

Abstract

To carry out the dehydration reaction of 4-methyl-2-pentanol and analyze the alkene product by gas chromatography. Later, chemical tests of Bromine, Baeyer and chromic acid on 4-methyl-2-pentanol and the product mixture is done.

Equations

Procedure Reference        

Marrs, P. Chemistry 323 Organic Chemistry Laboratory Manual, Spring 2016, 17-22, B19

Dehydration of 4-Methyl-2-pentanol

Table1: Reagents used in dehydration of 4-methyl-2-pentanol

Compound

MW

Used

Millimoles

Physical and Safety Data

4-methyl-2-pentanol C6H4O

102.17

5.001g

48.95

Hazardous in case of eye contact. Irritant d. 807.50kg/m2

85%Phosphoric acid H3PO4

98.00

5mL

72.9

Corrosive, wear protective clothing, gloves & eye protection. 85% by weight in H2O.

d 1.68 g/mL.

The limiting reagent is: 4-methyl-2pentanol

Table2: Product formed after the dehydration of 4-methyl-2-pentanol

Compound

MW

Isolated

moles

% yield

4-methyl-2-pentene C6H12

(Alkene Product from the GC table)

84.16g/mol

2.055g

0.0244

49.89

Observations:

My isolated product was clear. I did spill my alkene product during the chemical tests but I was able to weigh it properly calculate the % yield. However my sample I turned in will have significantly less than what is reported due to the spill.

Sample Calculations:

4-methyl-2-pentanol (millimoles) = mass used / molecular weight

= (5.001g) / (102.174g/mol)

= 0.04895 moles * (1000millimoles/1mole) = 48.95milimoles

85% phosphoric acid (millimoles) = (volume x density x percentage) / molecular weight

= (5mL x 1.68 g/mL x 0.85) / (98.0 g/mol)

= 0.07285moles * (1000millimoles/1mole) = 72.9millimoles

% yield based on limiting reagent:

Actual moles of 2-methyl-2-pentene = mass isolated / molecular weight

 = (2.0551g) / (84.16g/mol)

= 0.02442moles *(1000millimoles/1mole) = 24.42 millimoles

Percent (%) Yield of 4-methyl-2pentanol

= (actual moles) / (expected moles) x 100%

 = (24.42 millimoles) / (48.95) x 100% = 49.89%

Table 3: Results of the Gas Chromatographic Analysis

Component

Retention Time

% Composition                    (assume equal to % area)

2-methyl-2-pentene (My own Graph)

2.804

1.09

4-methyl-1-pentene (Graph Provided)

2.482

6.70

4-methyl-2-pentene (Graph Provided)

2.543

54.70

2-methyl-1-pentene (Graph Provided)

2.652

6.05

2-methyl-2-pentene (Graph Provided)

2.774

27.92

3-methyl-2-pentene (Graph Provided)

2.880

3.54

The GC analysis sheets are attached at the end of the report.

Table 4: Functional Group Tests

Unknown

Bromine Test

Baeyer Test

Chromic Acid test

Identity

A

Orange (-)

Purple(-)

Yellow (-)

Toluene

B

Colourless(+)

Brown(+)

Yellow(-)

Styrene

C

Orange(-)

Purple(-)

Green(+)

Benzly alcohol

D

Colourless(+)

Brown(+)

Green(+)

Cinnamyl alcohol

...

...

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