Textbook Question
Suggest an alkene to undergo hydroboration–oxidation (1. BH3 2. NaOH, H2O2) to give exclusively the alcohols shown. Pay close attention to the relative (but not absolute) stereochemical outcome.
(b)
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Ch. 8 - Alkenes I: Properties and Electrophilic Additions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 7, Problem 7d
What is the index of hydrogen deficiency for each of the following molecular formulas?
(d) C9H12N2O2
Verified step by step guidance1
Step 1: Understand the concept of the Index of Hydrogen Deficiency (IHD). The IHD, also known as the degree of unsaturation, indicates the number of rings, double bonds, or triple bonds in a molecule. It is calculated using the formula: IHD = (2C + 2 + N - H - X) / 2, where C = number of carbons, H = number of hydrogens, N = number of nitrogens, and X = number of halogens (if present). Oxygen atoms do not affect the IHD calculation.
Step 2: Identify the values for the molecular formula C₉H₁₂N₂O₂. Here, C = 9, H = 12, N = 2, and there are no halogens (X = 0). Oxygen atoms are present, but they do not contribute to the IHD calculation.
Step 3: Substitute the values into the IHD formula: IHD = (2(9) + 2 + 2 - 12 - 0) / 2. Simplify the expression step by step to determine the numerator.
Step 4: Divide the simplified numerator by 2 to calculate the IHD. This will give you the total number of rings and/or multiple bonds in the molecule.
Step 5: Interpret the result. If the IHD is 0, the molecule is fully saturated (no rings or multiple bonds). If the IHD is greater than 0, it indicates the presence of unsaturation, such as rings or double/triple bonds.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Index of Hydrogen Deficiency (IHD)
The Index of Hydrogen Deficiency (IHD) is a measure of the degree of unsaturation in a molecular formula. It indicates the number of rings and/or multiple bonds present in a compound. Each double bond or ring contributes one to the IHD, while each triple bond contributes two. The formula for calculating IHD is IHD = (2C + 2 + N - H - X) / 2, where C is the number of carbons, N is the number of nitrogens, H is the number of hydrogens, and X is the number of halogens.
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Molecular Formula Interpretation
A molecular formula provides the number of each type of atom in a compound. In the case of C₉H₁₂N₂O₂, it indicates there are 9 carbon atoms, 12 hydrogen atoms, 2 nitrogen atoms, and 2 oxygen atoms. Understanding how to interpret this formula is crucial for calculating the IHD, as it directly informs the values used in the IHD formula.
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Unsaturation and Stability
Unsaturation refers to the presence of double or triple bonds in a molecule, which affects its reactivity and stability. Compounds with higher IHD values typically have more unsaturation, making them more reactive due to the presence of pi bonds. Recognizing the implications of unsaturation is important for predicting the behavior of organic compounds in chemical reactions.
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Related Practice
Textbook Question
What is the index of hydrogen deficiency for each of the following molecular formulas?
(c) C8H14Cl2
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Textbook Question
What is the index of hydrogen deficiency for each of the following molecular formulas?
(e) C6H12O2
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Textbook Question
What is the index of hydrogen deficiency for each of the following molecular formulas?
(b) C12H11NO3
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Textbook Question
What is the index of hydrogen deficiency for each of the following molecular formulas?
(a) C6H12O6
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Textbook Question
Draw the molecular orbital picture of trans-but-2-ene.
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