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CHEM 237 CHEM237 Oxidation of a Secondary Alcohol with Sodium Hypochlorite – Texas A&M

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CHEM 237 CHEM237 Oxidation of a Secondary Alcohol with Sodium Hypochlorite – Texas A&M

CHEM 237 December 5 2016

Oxidation of a Secondary Alcohol with Sodium Hypochlorite

Objective:

To investigate the oxidation of a secondary alcohol with an environmentally friendly reagent, bleach, and use infrared spectroscopy to identify the starting alcohol and product formed.

Methods:

Sodium hypochlorite was used to oxidize an unknown secondary alcohol, while being monitoredby starch paper, to obtain a ketone product.

Description

  

CHEM 237 CHEM237 Oxidation of a Secondary Alcohol with Sodium Hypochlorite – Texas A&M

CHEM 237 December 5 2016

Oxidation of a Secondary Alcohol with Sodium Hypochlorite

Objective:

To investigate the oxidation of a secondary alcohol with an environmentally friendly reagent, bleach, and use infrared spectroscopy to identify the starting alcohol and product formed.

Methods:

Sodium hypochlorite was used to oxidize an unknown secondary alcohol, while being monitoredby starch paper, to obtain a ketone product.

Separation via seperatory funnel was performed after destroying excess oxidation with saturated sodium bisulfate solution, while being monitored with pH paper.

Distillation was also performed at a low heat to distill dichloromethane out, and then at a high setting to distill the ketone product formed.

To identify the starting alcohol and ketone product, an IR spectrum and boiling point were obtained and analyzed.

In Lab Observations:

Steps followed:The following experiment was conducted in pairs. An ice bath was first prepared to cool the reaction flask if necessary. A stir bar was added to a 50 mL Erlenmeyer flask, along with 1.325g of unknown alcohol “C”.

Then, 1.0 mL of acetic acid was added while the flask was clamped for securityand set on a low stir setting. A thermocouple was used to monitor the temperature of the reaction, while15 mL of NaOCl was added with a plastic pipette over an 11-minute period.

The reaction was tested with starch paper until the results were positive. In our case, no extra NaOCl was needed. Excess oxidant was destroyed by adding 0.5 mL of saturated sodium bisulfate until a negative starch paper test was given.

CHEM 237 CHEM237 Oxidation of a Secondary Alcohol with Sodium Hypochlorite – Texas A&M

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