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Chapter 22: Problem 143

Mycomycin, a naturally occurring antibiotic produced by the fungus Nocardia acidophilus, has the molecular formula \(\mathrm{C}_{13} \mathrm{H}_{10} \mathrm{O}_{2}\) and the systematic name \(3,5,7,8\) -tridecatetraene- 10,12 diynoic acid. Draw the structure of mycomycin.

Short Answer

Expert verified
The structure of mycomycin can be drawn as: \( \text{H}_{3}\text{C}-\text{CH}= \text{CH}-\text{CH}=\text{CH}-\text{CH}= \text{CH}-\text{CH}\)-\(\text{C}\equiv\text{C}\)-\( \text{CH}\equiv\text{C}-\text{COOH} \)

Step by step solution

01

Identify the functional groups from the systematic name

The systematic name of mycomycin is 3,5,7,8-tridecatetraene-10,12-diynoic acid. Based on this name, we can identify the following functional groups: 1. Alkene: The "triene" part of the name indicates three double bonds in the carbon chain. 2. Alkyne: The "diyn" part of the name indicates two triple bonds in the carbon chain. 3. Carboxylic acid: The "oic acid" part of the name indicates the presence of a carboxylic acid group. Based on this information, we can infer that mycomycin has 3 double bonds, 2 triple bonds, and 1 carboxylic acid group in its structure.
02

Determine the positions of the functional groups

The systematic name also provides the positions of the functional groups in the carbon chain: 1. The double bonds are at the 3, 5, 7, 8 positions. 2. The triple bonds are at the 10, 12 positions. 3. The carboxylic acid group is at the end of the carbon chain, as indicated by the "-oic acid" suffix.
03

Draw the carbon chain

Now we can draw the carbon chain of mycomycin with a total of 13 carbon atoms and the functional groups at their respective positions: 1. Begin with a straight chain of 13 carbon atoms. 2. Place the double bonds between carbons 3-4, 5-6, and 7-8. 3. Place the triple bonds between carbons 10-11 and 12-13.
04

Add the remaining hydrogen atoms and the carboxylic acid group

Next, we can add the hydrogen atoms to the carbon atoms such that each carbon atom has a total of four bonds. At the end of the carbon chain, replace the hydrogen atom on carbon-13 with the carboxylic acid group (-COOH). The final structure should look like this: \( \text{H}_{3}\text{C}-\text{CH}= \text{CH}-\text{CH}=\text{CH}-\text{CH}= \text{CH}-\text{CH}\)-\(\text{C}\equiv\text{C}\)-\( \text{CH}\equiv\text{C}-\text{COOH} \) This is the structure of mycomycin as described by its molecular formula and systematic name.

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