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 55a

Chapter 4, Problem 55a

Draw a condensed structure and a skeletal structure for each of the following:
a. sec-butyl tert-butyl ether

Verified step by step guidance

Step 1: Understand the structure of sec-butyl tert-butyl ether. This compound is an ether, meaning it contains an oxygen atom bonded to two alkyl groups. The two groups here are a sec-butyl group and a tert-butyl group.

Step 2: Recall the structure of a sec-butyl group. A sec-butyl group is a four-carbon chain where the second carbon is attached to the functional group (in this case, the oxygen atom). Its structure can be written as CH3-CH(CH3)-CH2-.

Step 3: Recall the structure of a tert-butyl group. A tert-butyl group is a branched alkyl group with three methyl groups attached to a central carbon. Its structure can be written as (CH3)3C-.

Step 4: Combine the two groups with the oxygen atom to form the ether. The oxygen atom will be bonded to the sec-butyl group on one side and the tert-butyl group on the other. The condensed structure can be written as CH3-CH(CH3)-CH2-O-C(CH3)3.

Step 5: Draw the skeletal structure. In the skeletal structure, carbon atoms are represented as vertices, and hydrogen atoms are implied. Draw a chain for the sec-butyl group, connect it to an oxygen atom, and then attach the tert-butyl group as a branched structure. Ensure all bonds and branches are correctly represented.

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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 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. For example, the condensed structure of sec-butyl tert-butyl ether can be represented as C4H9OC4H9, indicating the ether functional group connecting two alkyl chains.

Skeletal Structure

A skeletal structure, also known as a line-angle structure, is a way of drawing organic molecules that emphasizes the connectivity of atoms while omitting hydrogen atoms attached to carbons. In this representation, carbon atoms are represented by vertices or ends of lines, and functional groups are shown explicitly. This method is particularly useful for visualizing larger molecules and their functional groups, such as the ether linkage in sec-butyl tert-butyl ether.

Ether Functional Group

An ether functional group consists of an oxygen atom bonded to two alkyl or aryl groups, represented as R-O-R', where R and R' are the hydrocarbon chains. Ethers are characterized by their relatively low reactivity and are commonly used as solvents in organic reactions. Understanding the structure and properties of ethers is essential for drawing their condensed and skeletal forms accurately, as seen in sec-butyl tert-butyl ether.

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