Synthesis of N - 1 H g 13.11 singlet-1 Table 3 13 C NMR...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
Synthesis of N-Acetylanthranilic Acid from Anthranilic acid, Acetic Anhydride, and Water Natalie Chartrand Chemistry 2600 Lab Section 2 January 30, 2008
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Reaction Equations: OH O NH 2 O O O N O O 1 + H 3 O + CH 3 COO - + N O O OH O NH O 2 + H 2 O Table 1: Reagent / Product Table for Synthesis of N-Acetylanthranilic Acid Reaction 1 Reagents Products Name of Substance(s) Anthranilic acid Acetic anhydride Water N-Acetylanthranilic Acid Boiling point ( C) 138-140 100 Literature melting point ( C) 144-148 1 -73 0 184-187 Molecular weight (g/mol) 137.14 1 102.09 18.02 179.17 Density (g/mL) N/A 1.08 1.00 N/A Mass / Volume 0.481 g 1.50mL 0.50mL 0.172 Moles 3.51 x 10 -3 1.59 x 10 -2 2.78 x 10 -2 9.60 x 10 -4 Table 2: 1 H NMR Data for N-Acetylanthranilic Acid OH O NH O Figure 1: N-Acetylanthranilic acid Proton Chemical Shift (ppm) Multiplicity J value (Hz) Integration H a 2.13 singlet - 3H H b 7.12 triplet 7.5 1 H c 7.565 triplet 7.5 1 H d 7.96 doublet 6 1 H e 8.46 doublet 6 1 H f 11.05 singlet -
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 4
Background image of page 5
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 1 H g 13.11 singlet-1 Table 3: 13 C NMR Data for N-Acetylanthranilic Acid OH O NH O Figure 2: N-Acetylanthranilic acid Carbon atom Chemical Shift (ppm) C 1 25.44 C 2 116.87, 120.36, 122.98, 131.50, 134.45, 141.32 C 3 168.91 C 4 169.94 Conclusion: N-Acetylanthranilic acid was synthesized in a two step process: first, anthranilic acid and acetic anhydride were combined to form the intermediate, benzsoxazenone; next, water was added to the reaction mixture to produce the final product, N-Acetylanthranilic acid. OH O NH O Figure 3: N-Acetylanthranilic acid References: 1. Aldrich Book of Fine Chemicals, 2007-2008, page 241 2. Aldrich Book of Fine Chemicals, 2007-2008, page 79 3. Aldrich Book of Fine Chemicals, 2007-2008, page 92 Questions: Calculations:...
View Full Document

{[ snackBarMessage ]}

Page1 / 5

Synthesis of N - 1 H g 13.11 singlet-1 Table 3 13 C NMR...

This preview shows document pages 1 - 5. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online