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Chapter 23: Problem 65

Which IUPAC name is correct for the given compound? CC(C)=CCCC(C)=CC=O (a) 3,7 -dimethyloct- 2,6 -dienal (b) 2,6 -dimethyloct- 2,6 -dienal-8 (c) 7 -formyl-2, 6-dimethylhept \(-2,6\)-diene (d) 7 -aldo- 2,6 -dimethylhept- 2,6 -diene

Short Answer

Expert verified
The correct answer is (a) 3,7-dimethyloct-2,6-dienal.

Step by step solution

01

Identify Functional Groups

The compound has the SMILES representation `CC(C)=CCCC(C)=CC=O`. From this, we can identify that the compound contains an aldehyde group, which is indicated by the `C=O` at the end, making the suffix '-al' appropriate for naming.
02

Determine the Longest Carbon Chain

The longest carbon chain containing the aldehyde group is eight carbons. This makes the base name 'octane' since there are no rings present.
03

Locate Double Bonds

The SMILES shows two double bonds: one between carbon 2 and 3 \(\text{C=C}\) and another between carbon 6 and 7, making it a dienal with the designation 2,6-diene.
04

Identify Substituents

There are two methyl groups present on the main carbon chain. These are located at carbon 3 and carbon 7, indicating the name should have the prefix 3,7-dimethyl.
05

Combine the Elements of the Name

With the identified components: the main chain is octane, there are double bonds at positions 2 and 6, there are methyl groups at 3 and 7, and the aldehyde group is at position 1. This combination gives us the correct IUPAC name.

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Key Concepts

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

Aldehyde Group
In organic chemistry, recognizing functional groups is crucial for naming compounds accurately. An **aldehyde group** is one such important functional group, characterized by a carbon atom double-bonded to an oxygen atom at the end of a carbon chain. This group is often abbreviated as `-CHO`. When you see a carbon-oxygen double bond (`C=O`) at the end of a chain, you're looking at an aldehyde.
  • Aldehyde groups always appear at the end of carbon chains.
  • This placement affects how the compound is named, with the suffix '-al' indicating the presence of an aldehyde.
  • In the given compound SMILES `CC(C)=CCCC(C)=CC=O`, the `C=O` indicates the presence of an aldehyde group, guiding the choice of the suffix in its IUPAC name as 'dienal'.
Longest Carbon Chain
Determining the **longest carbon chain** in a molecule is another key step in IUPAC nomenclature. The longest chain is usually chosen to include the most significant functional group, such as an aldehyde, if present.
In our example:
  • We identified a chain of eight carbon atoms ( CC(C)=CCCC(C)=CC=O ), which includes the aldehyde group.
  • This eight-carbon chain results in the base name 'octane' for the compound.
  • It's critical to highlight that the longest chain must incorporate the aldehyde group to ensure correct suffix usage, with the aldehyde affecting the chain's functional priority.
Double Bonds
Molecules can feature **double bonds**, which influence both the name and the chemical behavior of the compound. A double bond consists of two pairs of shared electrons between two carbon atoms.
In the given compound:
  • The SMILES notation `CC(C)=CCCC(C)=CC=O` reveals double bonds between carbon positions 2 and 3, and 6 and 7.
  • The presence of these double bonds necessitates the use of 'diene' in the compound's name, reflecting the two double bonds at positions 2 and 6.
  • The positioning of double bonds is crucial, and changes to these locations can significantly alter the compound's properties and IUPAC name.
Methyl Group Substituents
**Methyl group substituents** are small functional groups, consisting of one carbon atom bonded to three hydrogen atoms, denoted as `-CH鈧僠. These substituents can be attached at various points on the main carbon chain and influence the official IUPAC naming.
For the compound with SMILES `CC(C)=CCCC(C)=CC=O`:
  • There are two methyl groups located at carbons 3 and 7.
  • The presence of these groups is indicated with the prefix 'dimethyl' in the name.
  • Identifying and accurately numbering the position of these substituents ensures the precise naming of the compound, as they signal modifications to the main structure.

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Most popular questions from this chapter

For each category of compounds the minimum number of carbons required for optical isomerism to be possible is given. Find the correct match (es). (a) Alkane \(-7\) (b) Alkene \(-6\) (c) Alkyl halide \(-4\) (d) Alkadiene - 7

Which class of compound can exhibit geometrical isomerism (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{NOH}\) (c) O=C(O)C=CC(=O)O (d) All of these

The IUPAC name of the compound shown below is [2006] ClC1CCCC(Br)C1 (a) 2-bromo-6-chlorocyclohex-1-ene (b) 6 -bromo-2-chlorocyclohexene (c) 3-bromo-1-chlorocyclohexene (d) 1-bromo-3-chlorocyclohexene

Match the following: List I List II 1\. \(\mathrm{CH}_{3} \mathrm{COOH}\) and \(\mathrm{HCOOCH}_{3}\) (i) metamers 2\. \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{C} \equiv \mathrm{CH}\) and (ii) position isomers \(\mathrm{CH}_{3}-\mathrm{C}=\mathrm{C}-\mathrm{CH}_{3}\) 3\. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) and (iii) tautomers \(\mathrm{CH}_{3}-\mathrm{CH}\left(\mathrm{NH}_{2}\right)-\mathrm{CH}_{3}\) 4\. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) and \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{O}\) (iv) functional isomer The correct matching is: \(\begin{array}{llll}1 & 2 & 3 & 4\end{array}\) (a) (iii) (iv) (i) (iv) (b) (i) (ii) (iii) (iv) (c) (iii) (ii) (i) (iv) (d) (iv) (ii) (ii) (iv)

Consider the following compounds given below and select the correct statement. (I) CC1(C)CC(Br)CC1(C)C (II) CCC(C)C(C)=O (III) CC(F)(Cl)Cl (IV) CC1CCCCC1=O (a) except (I) all have stereogenic centre (b) all have stereogenic centre (c) all have plane of symmetry (d) only II and III have stereogenic centre
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