Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure

Problem 55l

Chapter 4, Problem 55l

Draw a condensed structure and a skeletal structure for each of the following:
l. 5-isopropyldecane

Verified step by step guidance

Step 1: Understand the IUPAC name '5-isopropyldecane'. The parent chain is 'decane', which means it is a straight-chain alkane with 10 carbon atoms. The '5-isopropyl' indicates that there is an isopropyl group (-CH(CH3)2) attached to the 5th carbon of the decane chain.

Step 2: Draw the condensed structure for decane. This is a straight chain of 10 carbons, with each carbon bonded to the appropriate number of hydrogens to satisfy the octet rule. The general formula for an alkane is CnH2n+2.

Step 3: Add the isopropyl group to the 5th carbon of the decane chain. The isopropyl group is a branched alkyl group with the structure -CH(CH3)2. Replace one of the hydrogens on the 5th carbon with this group.

Step 4: Draw the skeletal structure. In a skeletal structure, each vertex represents a carbon atom, and hydrogens bonded to carbons are implied. Draw a straight chain of 10 carbons for decane, and add a branch at the 5th carbon to represent the isopropyl group.

Step 5: Double-check your structures to ensure that all carbons have four bonds and that the isopropyl group is correctly placed on the 5th carbon. Verify that the condensed and skeletal structures are consistent with the IUPAC name.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Video duration:

Was this helpful?

Key Concepts

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

Condensed Structure

A condensed structure is a simplified representation of a molecule that shows the arrangement of atoms and their connectivity without depicting all the bonds explicitly. In this format, groups of atoms are often grouped together, and hydrogen atoms attached to carbons are usually omitted for clarity. This structure helps in visualizing the molecular formula and understanding the overall composition of the compound.

Skeletal Structure

A skeletal structure, also known as a line-angle structure, is a representation of organic molecules where carbon atoms are represented by vertices or ends of lines, and hydrogen atoms are implied. This format emphasizes the connectivity between carbon atoms and functional groups while omitting hydrogen atoms for simplicity. It is particularly useful for visualizing larger organic molecules and their branching.

Isopropyl Group

The isopropyl group is a branched alkyl group derived from propane, consisting of three carbon atoms with the structure -C(CH3)2. In the context of 5-isopropyldecane, the isopropyl group is attached to the fifth carbon of a straight-chain decane, which consists of ten carbon atoms. Understanding the placement and structure of the isopropyl group is essential for accurately drawing the condensed and skeletal structures.

Recommended video:

Guided course