Textbook Question
Dimethylamine, (CH3)2NH, has a molecular weight of 45 and a boiling point of 7.4 °C. Trimethylamine, (CH3)3N, has a higher molecular weight (59) but a lower boiling point (3.5 °C). Explain this apparent discrepancy.
Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 4a,b,c
Give a systematic (IUPAC) name for each diol
(a) CH3CH(OH)(CH2)4CH(OH)C(CH3)3
(b) HO-(CH2)8-OH
(c) 
Verified step by step guidance1
Step 1: Analyze the structure of compound (a). Identify the longest carbon chain containing both hydroxyl groups. The parent chain has 8 carbons, and the hydroxyl groups are located on carbons 2 and 7. Assign the lowest possible locants to the hydroxyl groups.
Step 2: For compound (a), name the substituents. There is a tert-butyl group attached to carbon 7. Combine the substituent name with the parent chain name, ensuring proper placement of locants.
Step 3: Analyze compound (b). This is a straight-chain diol with 8 carbons. The hydroxyl groups are located at both ends of the chain (positions 1 and 8). Use the prefix 'octane' for the parent chain and add 'diol' to indicate two hydroxyl groups.
Step 4: For compound (c) (image provided), identify the parent chain as cyclohexene. The hydroxyl groups are located on carbons 1 and 2, and both are in cis configuration. Use the prefix 'cyclohexene' and add 'diol' to indicate two hydroxyl groups. Specify the stereochemistry as 'cis'.
Step 5: Combine all elements for each compound systematically. Ensure proper IUPAC naming conventions are followed, including locants, substituents, and stereochemistry where applicable.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
10mWas 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 for naming organic chemical compounds. It provides rules for naming based on the structure of the molecule, including the longest carbon chain, functional groups, and their positions. Understanding these rules is essential for accurately naming compounds, especially those with multiple functional groups like diols.
Recommended video:
Guided course
03:43
The different parts of an IUPAC name
Diols
Diols, also known as glycols, are organic compounds containing two hydroxyl (-OH) groups. Their properties and reactivity can differ significantly from those of alcohols with a single hydroxyl group. Recognizing the structure and functional groups of diols is crucial for determining their IUPAC names and understanding their chemical behavior.
Recommended video:
Guided course
01:49Provide the correct common and IUPAC name.
Structural Isomerism
Structural isomerism occurs when compounds have the same molecular formula but different structural arrangements of atoms. This concept is important in organic chemistry as it affects the physical and chemical properties of compounds. Identifying isomers is key when naming compounds, particularly for diols that may have multiple structural forms.
Recommended video:
Guided course
06:47Monosaccharides - D and L Isomerism
Related Practice
Textbook Question
For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.
(c) C3H6O
3
views
Textbook Question
For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.
(b) C4H10O
1
views
Textbook Question
For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.
(d) C3H4O
8
views
Textbook Question
Give a systematic (IUPAC) name for each diol
(d)
(e)
2
views
Textbook Question
Predict which member of each pair will be more soluble in water. Explain the reasons for your answers.
(a) hexan-1-ol or cyclohexanol
(b) heptan-1-ol or 4-methylphenol
(c) 3-ethylhexan-3-ol or octan-2-ol
(d) hexan-2-ol or cyclooctane-1,4-diol
(e)
2
views