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Ch.2 - Atoms, Molecules, and Ions
Chapter 2, Problem 86

Draw the structural formulas for four structural isomers of C4H9Br.

Verified step by step guidance
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Step 1: Understand that structural isomers are compounds with the same molecular formula but different structural arrangements of atoms.
Step 2: Start by drawing the longest carbon chain possible for C4H9Br, which is a four-carbon chain. This will be the straight-chain isomer, known as 1-bromobutane.
Step 3: Create a second isomer by moving the bromine atom to a different carbon in the straight chain. For example, place the bromine on the second carbon to form 2-bromobutane.
Step 4: Consider branching the carbon chain to form isomers with a three-carbon chain and a methyl group. Place the bromine on the primary carbon to form 1-bromo-2-methylpropane.
Step 5: Create another branched isomer by placing the bromine on the secondary carbon of the three-carbon chain, resulting in 2-bromo-2-methylpropane.

Key Concepts

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

Structural Isomers

Structural isomers are compounds that have the same molecular formula but differ in the arrangement of atoms. This can include variations in the connectivity of the carbon skeleton or the position of functional groups. For C4H9Br, the different structural isomers arise from how the carbon atoms are connected and where the bromine atom is attached.
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Alkyl Groups

Alkyl groups are derived from alkanes by removing one hydrogen atom, resulting in a group that can bond to other atoms. In the case of C4H9Br, the alkyl groups can be straight-chain or branched, influencing the structural isomers. Understanding the different alkyl groups, such as butyl and isobutyl, is essential for drawing the correct structural formulas.
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Bromine Substitution

Bromine substitution refers to the incorporation of a bromine atom into a hydrocarbon structure, which can occur at different positions in the carbon chain. The position of the bromine atom in the structural isomers of C4H9Br affects the properties and reactivity of the compounds. Recognizing where bromine can be attached is crucial for accurately representing the isomers.
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Related Practice
Textbook Question

Consider the following organic substances: ethylethanoate, ethylmethylether, hexanol, and propanone. (b) Which of these molecules contain a C = O group?

Textbook Question

Chloropropane is derived from propane by substituting Cl for H on one of the carbon atoms. (a) Draw the structural formulas for the two isomers of chloropropane.

Textbook Question

Chloropropane is derived from propane by substituting Cl for H on one of the carbon atoms. (b) Suggest names for these two compounds.

Textbook Question

Suppose a scientist repeats the Millikan oil-drop experiment but reports the charges on the drops using an unusual (and imaginary) unit called the warmomb (wa). The scientist obtains the following data for four of the drops: Droplet Calculated Charge (wa) A 3.84⨉10−8 B 4.80⨉10−8 C 2.88⨉10−8 D 8.64⨉10−8 (a) If all the droplets were the same size, which would fall most slowly through the apparatus?

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Textbook Question

Suppose a scientist repeats the Millikan oil-drop experiment but reports the charges on the drops using an unusual (and imaginary) unit called the warmomb (wa). The scientist obtains the following data for four of the drops: Droplet Calculated Charge (wa) A 3.84⨉10−8 B 4.80⨉10−8 C 2.88⨉10−8 D 8.64⨉10−8 (b) From these data, what is the best choice for the charge of the electron in warmombs?

Textbook Question

Suppose a scientist repeats the Millikan oil-drop experiment but reports the charges on the drops using an unusual (and imaginary) unit called the warmomb (wa). The scientist obtains the following data for four of the drops: Droplet Calculated Charge (wa) A 3.84⨉10−8 B 4.80⨉10−8 C 2.88⨉10−8 D 8.64⨉10−8 (c) Based on your answer to part (b), how many electrons are there on each of the droplets?