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Chapter 12: Problem 57

The following names are incorrect. Write the structural formula that agrees with the apparent name, and then write the correct name of the compound. (a) 2 -Ethylbutane (b) 2-Isopropyl-2-methylpentane (c) 5-Ethyl-1,1-methylcyclopentane (d) 3 -Ethyl- 3,5,5 -trimethylhexane (e) 1,2 -Dimethyl-4-ethylcyclohexane (f) 2,4 -Diethylpentane (g) 5,5,6,6 -Methyl-7,7-ethyldecane

Short Answer

Expert verified
The compounds are corrected as follows: (a) 3-Methylpentane, (b) 2,2-Dimethylhexane, (c) 3-Ethyl-1,1-dimethylcyclopentane, (d) 3,3,5-Trimethylheptane, (e) 1-Ethyl-2,4-dimethylcyclohexane, (f) 3,5-Dimethylheptane, (g) 5,5,7,7-Tetramethyloctane.

Step by step solution

01

Understand the Basic Rules of IUPAC Naming

The International Union of Pure and Applied Chemistry (IUPAC) provides rules for naming organic compounds. According to these rules, we must find the longest continuous carbon chain, use the lowest possible numbers for substituents, and order substituents alphabetically. Each compound name should reflect the actual structure of the compound. Keeping these rules in mind will guide the process of correcting the names.
02

Analyze Compound (a) 2-Ethylbutane

Locate the longest carbon chain for the given name structure. The name '2-Ethylbutane' suggests a butane backbone with an ethyl group on the second carbon. The longest carbon chain incorrectly named as 'butane' actually should be 'pentane.' Therefore, the correct structure has five carbons in a row; the ethyl group becomes a substituent. Correctly the name should be 'pentane' with a 3-methyl group, so it's 3-methylpentane.
03

Analyze Compound (b) 2-Isopropyl-2-methylpentane

For the name '2-Isopropyl-2-methylpentane', the longest chain should include the isopropyl and the extra carbon correctly. The proposed structure actually has a longest chain of 6 carbons, making it a hexane. Correct structure shows '2,2-dimethylhexane' because isopropyl becomes dimethyl at position 2 after counting the longest carbon chain.
04

Analyze Compound (c) 5-Ethyl-1,1-methylcyclopentane

In this structure, cyclic compounds have the base name reflecting the ring as the principal chain. '1,1-methyl' suggests two methyl groups on the first carbon which is impossible in a correct structure as it won't be carbon. Correct naming involves looking for the correct position and then renaming based on the longest substituent as '3-ethyl-1,1-dimethylcyclopentane.'
05

Analyze Compound (d) 3-Ethyl-3,5,5-trimethylhexane

This name suggests a 6-carbon chain. The correct naming must use the principle of the longest chain for substituting groups. It turns out that by correctly identifying the longest chain as heptane, simplify the naming into '3,3,5-trimethylheptane' by re-assigning positions according to lower values where possible.
06

Analyze Compound (e) 1,2-Dimethyl-4-ethylcyclohexane

Begin by identifying the principle ring structure; cyclohexane. This needs correcting because it's named incorrectly by the cyclohexane structure shouldn't have a 1,2-dimethyl at those positions. Correct structure rearranges as '1-ethyl-2,4-dimethylcyclohexane' based on accurate substituent ordering and numbering.
07

Analyze Compound (f) 2,4-Diethylpentane

For 2,4-Diethylpentane, the largest chain can't be pentane as two ethyl groups don't fit without extending the chain. The appropriate backbone makes it a hexane; thus, the correct name after substitution adjustment is '3,5-dimethylheptane.'
08

Analyze Compound (g) 5,5,6,6-Methyl-7,7-ethyldecane

Start by removing any inappropriate multiple substituents positioned around long chains like 'methyl' and 'ethyl' being doubled. The primary chain is evidently octane once more. Correct occurrence is examined as allety is balanced then creating '5,5,7,7-tetramethyloctane' considering correct counting pathway due to numbering mistakes.

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Key Concepts

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

IUPAC Naming Rules
The International Union of Pure and Applied Chemistry (IUPAC) provides a standardized approach to naming organic compounds. These rules ensure clarity and uniformity in the way compounds are represented by names. To understand these names correctly, follow these guidelines:

  • Identify the longest continuous chain of carbon atoms in the molecule. This becomes the backbone or base name, such as hexane or pentane.
  • Number the carbon atoms in the chain, starting from the end closest to any substituent groups, to ensure substituents have the lowest number possible.
  • Name the substituents (alkyl groups or other functional groups) as prefixes to the base name of the compound.
  • List multiple substituents alphabetically and use prefixes di-, tri-, etc., to indicate how many identical groups exist.
Correct IUPAC naming requires both an understanding of these rules and often a deep analysis of the compound structure to ensure accurate representation. Always verify the proposed name against these guidelines.
Structural Formula Correction
Ensuring the structural formula matches the compound's name requires attention to detail. Sometimes the name assigned to a compound does not reflect its structure, leading to errors in identification and communication.

  • The first step is to write down the name and visualize or draw the structure based on that name.
  • Check if the longest carbon chain according to the name matches the structure. If not, adjust the structure or change the name to correct it.
  • Substituent groups should be correctly placed on the backbone. Their position is crucial as it changes the identity of the compound.
  • For cyclic compounds, ensure that the ring structure aligns with the base name and that all substituents are positioned accurately.
Structural formula correction involves careful verification against IUPAC rules, as misnamed compounds can easily result in invalid representations.
Longest Carbon Chain Identification
Identifying the longest carbon chain in a molecule is essential for determining the fundamental name of an organic compound.

  • Begin by examining the entire molecular structure and counting the number of carbon atoms in continuous chains.
  • Select the chain that includes the maximum number of carbons, which will serve as the backbone for naming the compound.
  • If multiple chains of identical length exist, choose the one with the greatest number of substituents or variations.
  • This process helps avoid errors in naming, ensuring the basal structure reflects reality 鈥� for instance, transforming a misidentified hexane into an accurately named heptane.
Correct chain identification is imperative because inaccuracies lead to misunderstandings about a compound's properties and characteristics. Checking and confirming the correct carbon chain ensures the proper foundation for subsequent naming and structural analysis.

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Most popular questions from this chapter

Write the structures of all singly chlorinated products that form when 2,4 -dimethylpentane is reacted with \(\mathrm{Cl}_{2}\).

Locate and identify the functional groups in (a) propylene glycol, one of the major ingredients used in electronic cigarettes; (b) glutaric acid, produced in the body during the metabolism of lysine and tryptophan; (c) lactic acid, from sour milk; and (d) phenylalanine, an amino acid found in proteins.

Propane, commonly known as liquid petroleum (LP) gas, burns in air to yield \(\mathrm{CO}_{2}\) and \(\mathrm{H}_{2} \mathrm{O}\). Write a balanced equation for the reaction.

Give IUPAC names for the five isomers with the formula \(\mathrm{C}_{6} \mathrm{H}_{14}\)

Write condensed structures for the following molecular formulas. More than one isomer will be required for each. (a) Isomers of \(\mathrm{C}_{8} \mathrm{H}_{18}\) that contain three methyl groups and a longest chain of 5 carbons (b) Cyclohexanes with a chemical formula of \(\mathrm{C}_{8} \mathrm{H}_{16}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{O}\) (d) Ketones and aldehydes with \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\) (e) Write the line structures for (b) and (d).
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