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An amide is a functional group containing a carbonyl group bonded to a nitrogen atom or any compound containing the amide functional group. They usually form from nucleophilic substitutions of carboxylic acid derivates with amines. For this experiment, the synthesis of an amide is conducted using anhydrous conditions in an inert atmosphere. Specifically, an aluminum oxide surface is utilized along with acetic anhydride to react with an unknown primary amine. It is also used as an acid absorbed to neutralize the acetic acid by-product. This experiment uses techniques such as solid-liquid extraction, gravity filtration, IR spectroscopy, HNMR spectroscopy and melting point determination. For solid-liquid extraction, gravity filtration was used to separate the solid from the liquid product. Both IR spectroscopy and HMNR spectroscopy are used in this experiment. IR spectroscopy, or infrared spectroscopy, tells which bonds or functional groups are in a compound based on band positio
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Amide Synthesis on Aluminum Oxide Catalyst Introduction An amide is a functional group containing a carbonyl group bonded to a nitrogen atom or any compound containing the amide functional group. They usually form from nucleophilic substitutions of carboxylic acid derivates with amines. For this experiment, the synthesis of an amide is conducted using anhydrous conditions in an inert atmosphere. Specifically, an aluminum oxide surface is utilized along with acetic anhydride to react with an unknown primary amine. It is also used as an acid absorbed to neutralize the acetic acid by-product. This experiment uses techniques such as solid-liquid extraction, gravity filtration, IR spectroscopy, HNMR spectroscopy and melting point determination. For solid-liquid extraction, gravity filtration was used to separate the solid from the liquid product. Both IR spectroscopy and HMNR spectroscopy are used in this experiment. IR spectroscopy, or infrared spectroscopy, tells which bonds or functional groups are in a compound based on band positions. Certain absorbance bands at specific wavenumbers are unique per functional groups or bonds. HNMR, or hydrogen-1 nuclear magnetic resonance, spectroscopy is used to identify and confirm the identity of compounds. It tells how many protons are in the compound, how the protons are connected/interact in the compound, and how many different types of protons the compound has. Each peak in the HNMR spectrum shows a type of proton. The leftmost peak is the solvent peak and the rightmost is the reference peak, which are not counted as a proton. Each peak is at a certain ppm which will represent certain functional group’s proton. Both methods are used to determine and confirm identities of compounds. Balanced Mechanism:
Table of Reagents Compound Name Structure MW (g/mol)
Density (g/mL) Acetic anhydride
Aluminum oxide
Ethyl acetate
Safety Information
yellow in color. • The addition of ethyl acetate to mixture made it a murky white color liquid. • The unknown amine was a pale yellow/white liquid.
Limiting Reagent Calculation
a. N-(3-ethylpentyl)-2-methylpentanamide can be formed using 2-methylpentanoic anhydride, 3-ethylpentan-1-amine, and aluminum oxide. b. 2-methyl-N-(3-methylcyclohexyl)butanamide can be formed using 2- methylbutanoic anhydride, 3-methylcyclohexan-1-amine, and aluminum oxide. 3)a. b.