Textbook Question
Draw the structures of the following compounds. (Includes both new and old names.)
(a) triphenylmethanol
(b) 4-(chloromethyl)heptan-3-ol
(c) 2-cyclohexen-1-ol
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 10, Problem 32d,e
Draw the structures of the following compounds. (Includes both new and old names.)
(d) 3-cyclopentylhexan-3-ol
(e) meso-2,4-pentanediol
Verified step by step guidance1
Step 1: Begin by identifying the parent chain for each compound. For (d) 3-cyclopentylhexan-3-ol, the parent chain is hexane (a six-carbon chain). For (e) meso-2,4-pentanediol, the parent chain is pentane (a five-carbon chain).
Step 2: For (d), locate the substituent and functional group. The cyclopentyl group is attached to the third carbon of the hexane chain, and the hydroxyl (-OH) group is also attached to the third carbon. Draw the hexane chain first, then add the cyclopentyl group and hydroxyl group at the correct positions.
Step 3: For (e), note that meso compounds have internal symmetry and are optically inactive. The 2,4-pentanediol has hydroxyl (-OH) groups attached to the second and fourth carbons of the pentane chain. Ensure the stereochemistry is such that the molecule is symmetric (e.g., one hydroxyl group is on a wedge and the other on a dash).
Step 4: Add all necessary hydrogens to complete the structures. Ensure that each carbon has four bonds and the correct number of hydrogens to satisfy the valency of carbon.
Step 5: Double-check the structures for accuracy, ensuring the substituents and functional groups are correctly placed, and confirm that the meso compound has internal symmetry.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Structural Representation of Organic Compounds
Understanding how to draw the structures of organic compounds is fundamental in organic chemistry. This involves recognizing the arrangement of atoms, including carbon skeletons, functional groups, and stereochemistry. Familiarity with line-angle formulas and the ability to depict three-dimensional structures on a two-dimensional plane is essential for accurately representing compounds.
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01:40
Defining meso compounds.
Nomenclature of Organic Compounds
Organic nomenclature is the systematic method of naming organic chemical compounds based on their structure. The names provide information about the number of carbon atoms, functional groups, and the presence of stereoisomers. Knowing how to interpret and convert between IUPAC names and structural formulas is crucial for understanding the compounds in question.
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01:40Defining meso compounds.
Stereochemistry
Stereochemistry deals with the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the case of meso compounds, such as meso-2,4-pentanediol, it is important to recognize that they possess multiple stereocenters but are achiral due to an internal plane of symmetry. Understanding stereochemistry is vital for accurately drawing and interpreting the structures of compounds with chiral centers.
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Related Practice
Textbook Question
Give systematic (IUPAC) names for the following diols and phenols.
(a)
(b)
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Textbook Question
Draw the structures of the following compounds. (Includes both new and old names.)
(k) 3-methylhex-4-yn-2-ol
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Textbook Question
Give a systematic (IUPAC) name for each alcohol. Classify each as primary, secondary, or tertiary.
(f)
(g)
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Textbook Question
Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.
a. hexan-1-ol or 3,3-dimethylbutan-1-ol
b. hexan-2-one or hexan-2-ol
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Textbook Question
Draw the structures of the following compounds. (Includes both new and old names.)
i. cyclopent-3-ene-1-thiol
j. dimethyl disulfide
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