Atropine is an organic compound used to treat certain types of nerve agent and pesticide poisonings. — Organic Chemistry Chemistry Question
Atropine
Atropine is an organic compound used to treat certain types of nerve agent and pesticide poisonings. This compound can be synthesized from tropine and tropic acid in one step.
Tropine can be prepared as shown in the scheme below. The first step of this synthesis is “double Mannich reaction” (Robinson, 1917).
[VISUAL]
Write down the structural formulae of compounds A and B.
Model Answer
Organic chemical structures of compounds A and B as depicted in the solution on page 63 (A is succinaldehyde and B is tropinone).
Tropic acid can be prepared from the reaction of acetophenone and HCN followed by hydrolysis, elimination, addition and nucleophilic substitution (Mackenzie and Ward, 1919). In this synthesis, it should be noted that the electrophilic addition by HCl did not follow Markovnikov's Rule, and the anti-Markovnikov product (E) was obtained. Tropic acid (F) can also be prepared in only three steps from ethyl 2-bromo-2-phenylacetate and paraformaldehyde (Pernot, 1950). NMR data of tropic acid (F) are provided below.
1H NMR (400 MHz, d-DMSO): δ 12.35 (br, s, 1H), 7.34-7.25 (m, 5H), 4.91 (br s, 1H), 3.91 (dd, J = 10.0, 8.4 Hz, 1H), 3.64 (dd, J = 8.4, 6.0 Hz, 1H), 3.56 (dd, J = 10.0, 6.0 Hz, 1H).
13C NMR (101 MHz, d-DMSO) δ 173.7, 137.1, 128.4, 128.0, 127.1, 63.4, 54.3
Write down the structural formulae of compounds C-G in the diagram below.
[VISUAL]
Model Answer
Organic chemical structures of compounds C, D, E, F, and G as depicted in the solution on page 63.
When tropine was combined with tropic acid under acidic conditions, atropine was produced.
Write down the structural formula of atropine.
Model Answer
Organic chemical structure of atropine as depicted in the solution on page 63.
Predict the major products of the reactions shown below.
[VISUAL]
13C NMR spectrum of compound I shows nine signals in the range of 0 – 80 ppm, four signals in the range of 120 – 140 ppm, and one signal at 155 ppm. 13C NMR spectrum of compound J shows eight signals in the range of 0-80 ppm and one signal at 155 ppm. 13C NMR spectrum of compound K shows seven signals in the range of 0 – 80 ppm and four signals in the range of 120 – 140 ppm.
Model Answer
Organic chemical structures of compounds H, I, J, K, and L as depicted in the solution on page 63.