Textbook Question
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (vi) NaOH, H2O . If there is no reaction, write 'no reaction.'
(a)
2
views
Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
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. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 88a(i)
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 88a(i)Chapter 12, Problem 88a(i)
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (i) 1. BH3 2. NaOH, H2O2. If there is no reaction, write 'no reaction.'
(a) 
Verified step by step guidance1
Step 1: Recognize the reaction type. The given conditions (1. BH₃, 2. NaOH, H₂O₂) indicate hydroboration-oxidation, which is a two-step reaction used to convert alkenes into alcohols.
Step 2: Identify the functional group in the molecule. Hydroboration-oxidation specifically reacts with alkenes (C=C double bonds). If the molecule contains an alkene, proceed; otherwise, write 'no reaction.'
Step 3: Understand the regioselectivity of hydroboration. The addition of BH₃ to the alkene occurs in an anti-Markovnikov fashion, meaning the boron atom attaches to the less substituted carbon of the double bond.
Step 4: Oxidation step. In the second step, NaOH and H₂O₂ convert the boron group into a hydroxyl group (-OH), resulting in the formation of an alcohol. The hydroxyl group will be attached to the less substituted carbon of the original double bond.
Step 5: Predict the product. Draw the structure of the molecule after the hydroxyl group has been added to the less substituted carbon of the double bond. If no alkene is present in the starting molecule, write 'no reaction.'
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.
Hydroboration-Oxidation
Hydroboration-oxidation is a two-step reaction process used to convert alkenes into alcohols. In the first step, borane (BH₃) adds across the double bond of the alkene, resulting in a trialkylborane intermediate. The second step involves oxidation with hydrogen peroxide (H₂O₂) in the presence of a base (NaOH), which converts the boron atom into a hydroxyl group, yielding an alcohol.
Recommended video:
Guided course
06:38
General properties of hydroboration-oxidation.
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In hydroboration, the addition of borane occurs in a syn manner, favoring the formation of the more stable, less substituted alcohol product due to the anti-Markovnikov rule, where the boron atom attaches to the less substituted carbon of the alkene.
Recommended video:
Guided course
05:09Heck Reaction
Oxidation States
Oxidation states are a way to keep track of electron transfer in chemical reactions. In the context of hydroboration-oxidation, the oxidation state of carbon changes as the alkene is converted to an alcohol. Understanding how oxidation states change helps predict the products of reactions and assess the reactivity of different functional groups in organic compounds.
Recommended video:
Guided course
03:08Ground vs. Excited States
Related Practice
Textbook Question
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (ii) 1. Hg(OAc)2 2. NaBH4.If there is no reaction, write 'no reaction.'
(a)
1
views
Textbook Question
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (v) H2O. If there is no reaction, write 'no reaction.'
(a)
1
views
Textbook Question
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (v) H2O; (vi) NaOH, H2O. If there is no reaction, write 'no reaction.'
(f)
1
views
Textbook Question
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (iv) 1. OsO4 2. NaHSO3. If there is no reaction, write 'no reaction.'
(a)
4
views
Textbook Question
Predict the product(s) that would result when the following molecules are allowed to react under the following conditions: (i) 1. BH3 2. NaOH, H2O2 (ii) 1. Hg(OAc)2 2. NaBH4 (iii) H2SO4 , H2O (iv) 1. OsO4 2. NaHSO3 (v) H2O (vi) NaOH, H2O . If there is no reaction, write 'no reaction.'
(d)
5
views