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Amines

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Submitted By joemo18
Words 533
Pages 3
Name: Josiah Morales

Title: Amines

Introduction:
Amines are organic compounds containing nitrogen containing the functional group R−NH2. Amines are capable of forming hydrogen bonds and small amines are quite soluble in water. Amines are one of the primary functional groups in amino acids, and are often found as part of compounds that are physiologically active or used in medications. In this experiment, the identity of an unknown amine or amine salt had to be determined using Solubility testing and the Hinsberg test.

Apparatus and Materials: See Laboratory Manual, pages 40-42(Gary Gray. Laboratory Procedures: Organic Chemistry 2. Chemistry 3404. Wayland Baptist University, Plainview, TX.)

Procedure: See Laboratory Manual, pages 40-42(Gary Gray. Laboratory Procedures: Organic Chemistry 2. Chemistry 3404. Wayland Baptist University, Plainview, TX.)

Results:

Boiling point of unknown – 181 ͦC

Refractive index of unknown- 1.586

Solubility Test: Compound | Solubility | Odor | Aniline | - | Odor remained | Aniline hydrochloride | + | Odor formed then disappeared | Aniline sulfate | - | no odor | 4-Bromoaniline | - | Odor formed then disappeared | Methylamine hydrochloride | + | Odor remained | Pyridine | + | Odor remained | Unknown #4 | - | Odor remained |

Hinsberg Test: Compound | Reaction | Precipitate | Dissolved in Water | Aniline | - | - | - | N-Methylaniline | + | + | - | Triethylamine | + | - | - | Unknown Amine | - | - | - |

Infrared Spectrum of Unknown:

Discussion and Conclusion:
To determine the unknown amine, physical tests were done followed by two confirmatory test which were solubility and hinsberg respectively. The melting point was 181 ͦC and the refractive index was 1.586 indicating the unknown amine was aniline.
Most amines are soluble in water usually and dissolve in aqueous acid due to their ability to hydrogen bond. As the carbon chains get longer, solubility decreases as the hydrocarbon chains have to force their way between water molecules, breaking hydrogen bonds between water molecules. In the experiment the unknown was not soluble in water.
Secondly the Hinsberg test can distinguish primary, secondary, and tertiary amines and is based on sulfonamide formation. In the Hinsberg test, an amine is reacted with benzene sulfonyl chloride. If a product forms, the amine is either a primary or secondary amine, because tertiary amines do not form stable sulfonamides. If the sulfonamide that forms dissolves in aqueous sodium hydroxide solution, it is a primary amine. If the sulfonamide is insoluble in aqueous sodium hydroxide, it is a secondary amine. The sulfonamide of a primary amine is soluble in an aqueous base because it still possesses an acidic hydrogen on the nitrogen, which can be lost to form a sodium salt. The unknown did not react indicating it was a tertiary amine.
These results do not correspond with the compound aniline therefore there is some error in the experiment.

Problems: 1. Would you expect the reaction product from benzenesulfonyl chloride and ammonia to be soluble or insoluble in a basic solution? Explain.

The benzoyl chloride will react with the ammonia via a nucleophillic substitution reaction. The strong electron withdrawing sulphonyl group in benzene sulphonamide makes the hydrogen atom linked to nitrogen to become strongly acidic making it is soluble in a basic solution like KOH or NAOH.

2. How would you prepare aniline from aniline hydrochloride?

I would add a strong base such as NaOH or KOH to the aniline hydrochloride to obtain aniline.

3. Predict the NMR spectrum of 2-propanamine.

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