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Chapter 8: Problem 22

An unusual sphingosine variant has recently been isolated from the nerve of the squid Loligo pealeii. Its chemical name is 2 -amino9 -methyl- \(4,8,10\)-octadecatriene-1,3-diol. Draw the structure of this sphingosine variant.

Short Answer

Expert verified
Draw an 18-carbon chain with double bonds at C4, C8, and C10, an amino group at C2, a methyl group at C9, and hydroxyl groups at C1 and C3.

Step by step solution

01

Analyze the Hydrocarbon Chain

The IUPAC name provided is 2-amino-9-methyl-(4,8,10)-octadecatriene-1,3-diol. The backbone is an octadecatriene, which indicates a hydrocarbon chain with 18 carbon atoms and three double bonds at specific locations.
02

Identify the Double Bond Positions

The positions of the double bonds are specified as 4, 8, and 10. This means the double bonds are located between carbon 4 & 5, 8 & 9, and 10 & 11.
03

Add Functional Groups

The name indicates a 2-amino group, a 9-methyl group, and two hydroxyl (-OH) groups at positions 1 and 3. Place an amino group (-NH2) on carbon 2, a methyl group (-CH3) on carbon 9, and hydroxyl groups on carbons 1 and 3.
04

Construct the Complete Structure

Assemble your findings to create the chemical structure: an 18-carbon chain with double bonds at positions 4, 8, and 10; a 2-amino group; a 9-methyl substituent; and 1,3-diol functional groups. Make sure the double bonds are in the correct cis/trans configuration if specified, though not indicated here.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

IUPAC Nomenclature
The International Union of Pure and Applied Chemistry (IUPAC) system is like a guideline book for chemists worldwide, helping them name chemical substances in a way that outlines what molecules look like. It ensures consistency and precise communication across different regions and languages. The IUPAC name for the sphingosine in the squid's nerve tissue is 2-amino-9-methyl-(4,8,10)-octadecatriene-1,3-diol.
  • This name reveals a lot about the molecule. The term 'octadecatriene' suggests it's a compound with 18 carbon atoms and three double bonds.
  • The numbers 4, 8, and 10 tell where the double bonds are within that chain.
  • '2-amino' and '9-methyl' help locate specific groups attached to the chain, namely an amino group at carbon 2 and a methyl group at carbon 9.
  • The '1,3-diol' part indicates that there are hydroxyl groups (alcohol groups) present at carbon positions 1 and 3.
By understanding the IUPAC name, chemists can determine the full chemical structure without even seeing the molecule directly.
Chemical Structure Drawing
Drawing a chemical structure based on its IUPAC name involves visualizing the connections and bonds between atoms. In organic chemistry, it's like piecing together a molecular jigsaw.
  • Start with the longest carbon chain mentioned (octadecatriene) as the backbone. This should be 18 carbon atoms long.
  • Sketch in the double bonds at the positions specified, between the correct carbon pairs: between carbons 4 & 5, 8 & 9, and 10 & 11.
  • Add the functional groups identified in the name. The amino group goes on the second carbon, the methyl group on the ninth.
  • The diol portion signifies hydroxyl groups, which you'll place on the first and third carbon.
Never forget the importance of the geometrical configuration of double bonds and substituents. For instance, though not stated here, knowing if a double bond is cis or trans can be crucial for understanding the molecule's behavior and properties. Chemical structure drawings serve as a functional representation, guiding you to intuitively comprehend the molecule's three-dimensional layout.
Functional Groups Identification
Functional groups are specific clusters of atoms within molecules that are responsible for characteristic chemical reactions. Recognizing these groups allows chemists to predict how a molecule will behave.
  • An amino group (-NH2) acts as a base, often participating in reactions where it donates a pair of electrons. In this molecule, it is found at carbon 2.
  • The hydroxyl groups (-OH), as seen in the diol portion of the name, are common in alcohols and are seen at carbons 1 and 3. These groups are polar and can form hydrogen bonds, influencing solubility and reactivity.
  • The methyl group (-CH3), a simple hydrocarbon, is attached to carbon 9. It can affect how the entire molecule interacts with others, despite its relative simplicity.
Identifying and understanding these functional groups is crucial. They help predict how the sphingosine variant, with its unique combination of groups, might function biologically and chemically. By recognizing these groups, you gain insights into the molecule's chemical nature and potential activities.

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