AMIDE SYNTHESIS LAB REPORT, Lab Reports of Organic Chemistry

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:
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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)

MP

(°C)

BP

(°C)

Density (g/mL) Acetic anhydride

Aluminum oxide

Ethyl acetate

Safety Information

  • Always wear safety glasses, lab gloves, mask, and lab coat.
  • Handle amines with caution because they are basic and corrosive.

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.

  • The acetic anhydride was a clear liquid.
  • The ethyl acetate was a clear liquid.
  • The amine, Al2O3, and acetic anhydride mixture smells like vinegar. • The Al2O3 is a white solid. It is a bit powdery in texture.
  • For gravity filtration, the Al2O3 was on the filter paper and the product mixture in the beaker was a transparent light yellow liquid.
  • Beaker + product: 140.848 g
  • Final product was a thick yellow liquid with texture like oil. It smelled like nail polish. Results Unknown IR Spectra: HNMR Spectra:

Limiting Reagent Calculation

  • Acetic anhydride: 1.0 mL acetic anhydride * (1.083 g/mL) * (1 mol / 102.09 g) * (1 mol product/ 1 mol acetic anhydride) = 0.0106 mol N-phenylacetamide • Unknown amide: 1.0 mL * (1.02 g/mL) * (1 mol / 93.13 g) * (1 mol N product / 1 mol amine) = 0.0110 mol product.
  • Limiting reagent is acetic anhydride. Percent Yield Calculation
  • Theoretical Yield: 0.0106 mol product * (135.17 g/mol) = 1.433 g N-product
  • Percent Yield: (0.676 g / 1.433 g) * 100 = 47.17% Discussion: The product of this experiment was N-(tert-butyl)acetamide which means that the unknown amine used was tert-butyl amine. For the IR spectrum of the product There is also a C=O carbonyl stretch at 1600 cm^-1 which shows it is an amide. There are also N-Hstretches at roughly 3300 cm^-1 to 3500 cm^-1 as well as one N-H stretch at 3200 cm -1. There are also stretches at roughly 3000 cm^-1 and 3100 cm^-1 which shows there are Csp3-H and Csp2-H bonds respectively. All of these stretches and groups are seen in the product N-phenylacetamide. For the HNMR spectrum of the product, we see a broad IH singlet which is indicative of the NH proton, a 3 H singlet (methyl group) and a 9H singlet (tert-butyl group) These peaks

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.