Textbook Question
Unlike hydroboration–oxidation, the addition of H2O catalyzed by H3O+ is not stereospecific. Thinking carefully about the mechanism of the reaction, give two reasons why.
1
views
Ch. 8 - Alkenes I: Properties and Electrophilic Additions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Mullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 58b
Mullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 58bChapter 7, Problem 58b
Calculate the index of hydrogen deficiency for the following molecular formulas and structures.
(b) 
Verified step by step guidance1
Step 1: Understand the concept of the Index of Hydrogen Deficiency (IHD). IHD is a measure of the number of degrees of unsaturation in a molecule. Each degree of unsaturation corresponds to either a double bond, a ring, or a triple bond. The formula for IHD is: IHD = (2C + 2 - H - X + N)/2, where C is the number of carbons, H is the number of hydrogens, X is the number of halogens (like Br), and N is the number of nitrogens.
Step 2: Count the number of carbons (C), hydrogens (H), and halogens (X) in the given structure. From the image, the molecule contains 6 carbons, 9 hydrogens, and 1 bromine atom.
Step 3: Substitute the values into the IHD formula. Using the formula IHD = (2C + 2 - H - X + N)/2, substitute C = 6, H = 9, X = 1, and N = 0 (since there are no nitrogen atoms in the structure).
Step 4: Simplify the equation step by step. First, calculate the numerator: (2 * 6 + 2 - 9 - 1 + 0). Then divide the result by 2 to find the IHD.
Step 5: Interpret the result. The IHD value indicates the number of degrees of unsaturation in the molecule, which corresponds to the presence of rings or double/triple bonds. In this case, the structure contains one ring, which contributes to the IHD.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
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 counts as 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.
Recommended video:
Guided course
01:15
What index of hydrogen deficiency is.
Chemical Structure Interpretation
Understanding chemical structures is crucial for determining the IHD. The structure provides information about the connectivity of atoms, the presence of functional groups, and the overall geometry of the molecule. In the provided image, the presence of a bromine atom and the cyclic structure indicates potential unsaturation, which must be accounted for when calculating the IHD.
Recommended video:
Guided course
06:06How to interpret condensed structures.
Halogens and Their Effect on IHD
Halogens, such as bromine, affect the calculation of the IHD because they can replace hydrogen atoms in a molecular formula. Each halogen atom is treated as if it were a hydrogen atom in the IHD formula. Therefore, when calculating IHD, the presence of bromine in the structure must be included in the count of atoms to ensure an accurate assessment of the compound's saturation level.
Recommended video:
Guided course
03:45Halogenation Mechanism
Related Practice
Textbook Question
The first step of oxymercuration–reduction is stereospecific, and yet this fact wasn't emphasized in that discussion. Show the stereospecificity of the first step for the following alkene and then explain why the stereospecificity becomes unimportant after the second step.
2
views
Textbook Question
Calculate the index of hydrogen deficiency for the following molecular formulas and structures.
(c)
2
views
Textbook Question
Calculate the index of hydrogen deficiency for the following molecular formulas and structures.
(f) C6H8O2
4
views
Textbook Question
Calculate the index of hydrogen deficiency for the following molecular formulas and structures.
(a)
2
views
Textbook Question
Using IUPAC rules, name the following molecules.
(a)
1
views