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Chapter 22: Problem 163

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 complete structure for mycomycin is \(\mathrm{H}_{3}\mathrm{C}-\equiv\mathrm{C}-\equiv\mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2}-\mathrm{COOH}\).

Step by step solution

01

Identify the carbon backbone

According to the systematic name, the carbon backbone contains 13 carbons (trideca). From the name, we know it contains four double bonds (tetraene) between carbons 3, 5, 7, and 8.
02

Add the double bonds

Now add the double bonds between carbons 3, 5, 7, and 8. Remember, double bonds mean that there are two shared pairs of electrons between these pairs of carbon atoms.
03

Add the triple bonds

The systematic name also indicates two triple bonds (diynoic acid) between carbons 10 and 12. Add triple bonds between these carbons, representing these shared pairs of electrons.
04

Add the acid functional group

The name ends with "acid," indicating a carboxylic acid functional group. Attach the carboxylic acid group (COOH) to the carbon on the end opposite the double and triple bonds.
05

Add hydrogens

Now that we've added the other functional groups, we can fill in the remaining valences on the carbons with hydrogen atoms. Each carbon should have four bonds. A double bond counts as 2, a triple bond counts as 3, and a single bond counts as 1. Here is the complete structure for mycomycin: \( \begin{array}{c} \mathrm{H}_{3}\mathrm{C}-\equiv\mathrm{C}-\equiv\mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2}-\mathrm{COOH} \end{array} \) Note that there are several ways to draw the same molecule, and this representation is just one possible structural formula for mycomycin.

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Most popular questions from this chapter

Tautomers are molecules that differ in the position of a hydrogen atom. A tautomeric form of thymine has the structure If this tautomeric form, rather than the stable form of thymine, were present in a strand of DNA during replication, what would be the result?

Name all the aldehydes and ketones that have the formula$\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}$ .

Ethyl caprate is an ester used in the manufacture of wine bouquets. It is sometimes called "cognac essence." Combustion analysis of a sample of ethyl caprate shows it to be 71.89\(\% \mathrm{C}\) , 12.13\(\%\) hydrogen, and 15.98\(\%\) O by mass. Hydrolysis (reaction with water) of the ester produces ethanol and a carboxylic acid. The molar mass of the carboxylic acid is 172 \(\mathrm{g} / \mathrm{mol}\) , and the \(\mathrm{R}\) group attached to the COOH group of the acid is a straight chain alkane. What is the structure of ethyl caprate?

Use shorthand line notation (see Exercise 125\()\) to illustrate the structural isomers of \(\mathrm{C}_{7} \mathrm{H}_{16}\) .

Complete the following reactions. $$ \begin{array}{l}{\text { a. } \mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}+\mathrm{CH}_{3} \mathrm{OH} \rightarrow} \\ {\text { b. } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{HCOOH} \rightarrow}\end{array} $$
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