Textbook Question
Draw both condensed and line structures corresponding to the following IUPAC names and label each carbon as primary, secondary, tertiary, or quaternary.
c. 2,2,4-Trimethylpentane
Ch.12 Introduction to Organic Chemistry: Alkanes
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch.1 Matter and Measurements27
- Ch.2 Atoms and the Periodic Table20
- Ch.3 Ionic Compounds8
- Ch.4 Molecular Compounds23
- Ch.5 Classification & Balancing of Chemical Reactions12
- Ch.6 Chemical Reactions: Mole and Mass Relationships28
- Ch.7 Chemical Reactions: Energy, Rate and Equilibrium64
- Ch.8 Gases, Liquids and Solids24
- Ch.9 Solutions52
- Ch.10 Acids and Bases25
- Ch.11 Nuclear Chemistry22
- Ch.12 Introduction to Organic Chemistry: Alkanes57
- Ch.13 Alkenes, Alkynes, and Aromatic Compounds47
- Ch.14 Some Compounds with Oxygen, Sulfur, or a Halogen50
- Ch.15 Aldehydes and Ketones45
- Ch.16 Amines42
- Ch.17 Carboxylic Acids and Their Derivatives57
- Ch.18 Amino Acids and Proteins82
- Ch.19 Enzymes and Vitamins63
- Ch.20 Carbohydrates44
- Ch.21 The Generation of Biochemical Energy65
- Ch.22 Carbohydrate Metabolism45
- Ch.23 Lipids42
- Ch.24 Lipid Metabolism33
- Ch.25 Protein and Amino Acid Metabolism24
- Ch.26 Nucleic Acids and Protein Synthesis45
McMurry8th EditionFundamentals of General, Organic, and Biological ChemistryISBN: 9780134015187Not the one you use?Change textbook
Chapter 12, Problem 17
Write the structures of all singly chlorinated products that form when 2,4-dimethylpentane is reacted with Cl2.
Verified step by step guidance1
Identify the structure of 2,4-dimethylpentane. It is a branched alkane with a five-carbon chain (pentane) and two methyl groups attached to carbons 2 and 4.
Understand that chlorination with Cl₂ in the presence of light (or heat) proceeds via a free radical substitution mechanism, where a hydrogen atom is replaced by a chlorine atom.
Determine all unique hydrogen atoms in the molecule. In 2,4-dimethylpentane, there are primary, secondary, and tertiary hydrogens. Each type of hydrogen can lead to a different chlorinated product.
Replace one hydrogen atom at a time with a chlorine atom, considering all unique positions. For example, replacing a hydrogen on the primary carbon (e.g., at carbon 1 or 5), secondary carbon (e.g., at carbon 2 or 4), or tertiary carbon (e.g., at carbon 3) will yield different products.
Draw the structures of all possible singly chlorinated products, ensuring that each product corresponds to a unique substitution site. Verify that no two products are identical (i.e., they are not structural isomers of the same compound).
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Chlorination Reaction
Chlorination is a type of substitution reaction where chlorine (Cl₂) replaces hydrogen atoms in organic compounds. In the case of alkanes, this reaction typically occurs under UV light or heat, leading to the formation of chlorinated products. Understanding this process is crucial for predicting the products formed when 2,4-dimethylpentane reacts with chlorine.
Recommended video:
Guided course
0:47
Halogenation Reactions Example 1
Stereochemistry
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical properties. In the case of 2,4-dimethylpentane, the presence of multiple chiral centers can lead to different stereoisomers when chlorination occurs. Recognizing the stereochemical implications is essential for accurately identifying all possible chlorinated products.
Recommended video:
Guided course
1:30D vs L Enantiomers Concept 1
Product Distribution
Product distribution in a chemical reaction describes the relative amounts of different products formed. In chlorination reactions, the distribution can be influenced by factors such as the stability of the resulting radicals and steric hindrance. Analyzing the product distribution helps in understanding which chlorinated products are more likely to form when 2,4-dimethylpentane is reacted with Cl₂.
Recommended video:
Guided course
01:37Solubility Product Constant (Ksp) Concept 2
Related Practice
Textbook Question
What is wrong with the following names? It will be helpful to draw the structures as named before making your decision.
c. 1-Ethyl-2-methyl-3-ethylcyclopentane
Textbook Question
Convert the following models into line drawings (back = C; white = H; blue = N):
a.
Textbook Question
What are the IUPAC names of the following cycloalkanes? Remember to assign priority to the attached groups alphabetically.
b.
Textbook Question
Draw and name alkanes that meet the following descriptions:
a. A 5-carbon alkane with a tertiary carbon atom
Textbook Question
What are the IUPAC names of the following alkanes?
a.