Ch.3 - Structure and Stereochemistry of Alkanes

Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook

Wade 9th Edition

Ch.3 - Structure and Stereochemistry of Alkanes

Problem 8a

Chapter 3, Problem 8a

Draw the structures of the following compounds.
a. 4-(1,1-dimethylethyl)octane

Verified step by step guidance

Identify the main chain: The main chain is 'octane', which means it consists of 8 carbon atoms in a straight chain.

Number the carbon atoms in the main chain: Start numbering from one end of the chain to the other, ensuring that the substituent gets the lowest possible number. In this case, number the carbon atoms from 1 to 8.

Locate the substituent: The substituent is '4-(1,1-dimethylethyl)', which means it is attached to the 4th carbon of the octane chain.

Draw the substituent: The '1,1-dimethylethyl' group is a tert-butyl group, which consists of a central carbon atom bonded to three methyl groups (CH₃). Draw this group attached to the 4th carbon of the octane chain.

Complete the structure: Ensure that all carbon atoms have four bonds, adding hydrogen atoms as necessary to satisfy the valency of carbon. The final structure should show the octane chain with the tert-butyl group attached to the 4th carbon.

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.

IUPAC Nomenclature

IUPAC nomenclature is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry. It ensures that each compound has a unique name, which describes its structure. Understanding the rules of IUPAC nomenclature is essential for interpreting and drawing chemical structures from names.

Alkane Structure

Alkanes are saturated hydrocarbons consisting of carbon and hydrogen atoms with single bonds. The general formula for alkanes is CnH2n+2. Recognizing the structure of alkanes, such as octane, is crucial for drawing the backbone of the compound before adding substituents like the 1,1-dimethylethyl group.

Substituent Groups

Substituent groups are atoms or groups of atoms that replace hydrogen atoms in a hydrocarbon chain. In the given compound, 1,1-dimethylethyl is a substituent group attached to the fourth carbon of the octane chain. Understanding how to identify and position substituents correctly is key to accurately drawing the compound's structure.

Recommended video:

Guided course

04:42

Sequence Groups

Related Practice

Textbook Question

Draw the structures of the following groups, and give their more common names.

a. the (1-methylethyl) group

b. the (2-methylpropyl) group

c. the (1-methylpropyl) group

d. the (1,1-dimethylethyl) group

e. the (3-methylbutyl) group, sometimes called the 'isoamyl' group

1440

views

Textbook Question

Draw the structures of the following compounds.

c. 3,3-diethyl-4-(2,2-dimethylpropyl)octane

1713

views

Textbook Question

Without looking at the structures, give molecular formulas for the compounds: (a) 4-(1,1-dimethylethyl)octane and (b) 5-(1,2,2-trimethylpropyl)nonane. Use the names of the groups to determine the number of carbon atoms; then use the (2n + 2) rule.

1688

views

Textbook Question

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly.

d. 4-isobutylheptane

e. 2-bromo-3-ethylbutane

f. 2,3-diethyl-5-isopropylheptane

1183

views

Textbook Question

Draw the structures of the following compounds.

b. 5-(1,2,2-trimethylpropyl)nonane