Skip to main content
Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
All textbooksBruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 67a,b
Chapter 4, Problem 67a,b

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.
a. 4-bromo-3-pentanol
b. 2,2-dimethyl-4-ethylheptane

Verified step by step guidance
1
Step 1: Analyze the first compound, 4-bromo-3-pentanol. Start by identifying the parent chain. The parent chain should be the longest continuous chain containing the hydroxyl (-OH) group, which is prioritized in naming alcohols. Verify that the chain is correctly numbered to give the hydroxyl group the lowest possible number.
Step 2: Check the substituents in 4-bromo-3-pentanol. Confirm that the bromine atom is correctly located at carbon 4 and the hydroxyl group is at carbon 3. If the numbering does not prioritize the hydroxyl group, rename the compound accordingly.
Step 3: Analyze the second compound, 2,2-dimethyl-4-ethylheptane. Start by identifying the parent chain. The parent chain should be the longest continuous chain of carbon atoms. Verify that the chain is correctly numbered to give the substituents the lowest possible locants.
Step 4: Check the substituents in 2,2-dimethyl-4-ethylheptane. Confirm that the ethyl group is at carbon 4 and the two methyl groups are at carbon 2. If the numbering does not follow the IUPAC rules for substituent priority and lowest locants, rename the compound accordingly.
Step 5: Compare the corrected names (if any) to the original names provided. Determine how many names were correct and provide the corrected names for any misnamed compounds.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
8m
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for identifying the structure of a compound based on its molecular formula and functional groups. Understanding these rules is essential for correctly naming compounds, as it ensures that each name reflects the compound's structure and composition.
Recommended video:
Guided course
03:43
The different parts of an IUPAC name

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups, such as alcohols, alkenes, and halides, is crucial for naming compounds accurately, as they influence the naming conventions and the overall classification of the compound.
Recommended video:
Guided course
02:36
Identifying Functional Groups

Chain Length and Substituents

The chain length and the presence of substituents are key factors in determining the systematic name of a compound. The longest continuous carbon chain is identified as the parent chain, while substituents are named and numbered based on their position on this chain. Correctly identifying the main chain and the substituents is vital for accurate nomenclature.
Recommended video:
2:36
Side-Chain Reactions of Substituted Pyridines Concept 1
Related Practice
Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

c. 5-methylcyclohexanol

d. 1,1-dimethyl-2-cyclohexanol

2
views
Textbook Question

Draw a picture of the hydrogen bonding in methanol.

4
views
Textbook Question

Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-inflammatory drugs (NSAIDs). Both are only slightly soluble in water, but one is a little more soluble than the other. Which of the drugs has the greater solubility in water?

5
views
Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

e. 5-(2,2-dimethylethyl)nonane

f. isopentylbromide

1
views
Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

g. 3,3-dichlorooctane

1
views
Textbook Question

c. Draw Newman projections of the two conformers of the trans isomer.

d. Which of the conformers predominates at equilibrium?

1
views