Textbook Question
How many sets of equivalent hydrogens are in each molecule shown?
(c)
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Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy
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
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Mullins 1st EditionCh. 15 - Structural Identification II: Nuclear Magnetic Resonance SpectroscopyProblem 9
Mullins 1st EditionCh. 15 - Structural Identification II: Nuclear Magnetic Resonance SpectroscopyProblem 9Chapter 14, Problem 9
Calculate the index of hydrogen deficiency for curacin A, which has a molecular formula of C23H35NOS .
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 molecular formula and accounts for the presence of heteroatoms like oxygen, nitrogen, and sulfur.
Step 2: Use the general formula for IHD: IHD = (2C + 2 - H + N - X) / 2, where C is the number of carbons, H is the number of hydrogens, N is the number of nitrogens, and X is the number of halogens. Oxygen and sulfur do not affect the IHD calculation and are ignored in this formula.
Step 3: Substitute the values from the molecular formula of curacin A (C₂₃H₃₅NOS) into the formula. Here, C = 23, H = 35, N = 1, and there are no halogens (X = 0).
Step 4: Perform the calculation step-by-step. First, calculate the numerator: (2 × 23) + 2 - 35 + 1. Then divide the result by 2 to determine the IHD.
Step 5: Interpret the result. The IHD value represents the total number of rings and/or π-bonds in the structure of curacin A. This information can help deduce structural features of the molecule.
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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 molecule, indicating the number of rings and/or multiple bonds present. It is calculated using the formula 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. A higher IHD value suggests more unsaturation, which can affect the molecule's reactivity and stability.
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Molecular Formula Interpretation
A molecular formula provides the number and types of atoms in a molecule, which is essential for calculating the IHD. In the case of curacin A, the formula C₂₃H₃₅NOS indicates the presence of 23 carbon atoms, 35 hydrogen atoms, one nitrogen atom, one oxygen atom, and one sulfur atom. Understanding how to interpret this formula is crucial for applying the IHD calculation correctly.
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Unsaturation and Its Implications
Unsaturation refers to the presence of double bonds or rings in a molecule, which can significantly influence its chemical properties and reactivity. Each degree of unsaturation typically corresponds to a double bond or a ring structure. Recognizing the implications of unsaturation is vital for predicting how a molecule like curacin A will behave in chemical reactions, as well as its physical properties.
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Related Practice
Textbook Question
How many sets of equivalent hydrogens are in each molecule shown?
(a)
1595
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Textbook Question
How many sets of equivalent hydrogens are in each molecule shown?
(b)
1272
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Textbook Question
The spectrum shown here is for a molecule with a molecular formula of C₄H₉Cl. Suggest a structure for this molecule.
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Textbook Question
Draw the peak that would correspond to the hydrogens at C₃ in the molecule shown. Be sure to indicate the integration and place it at an appropriate chemical shift.
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Textbook Question
Every number in Pascal’s triangle is the sum of the two numbers above it. Given this, fill in the missing numbers.
1168
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