Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(a)
833
views
Ch.8 - Reactions of Alkenes
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 8, Problem 51h
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(h) 
Verified step by step guidance1
Step 1: Begin with methylenecyclohexane as the starting material. This compound contains a cyclohexane ring with a methylene group (CH2) attached via a double bond.
Step 2: Perform a hydroboration-oxidation reaction to convert the double bond into an alcohol group. Use BH3 (borane) followed by H2O2 (hydrogen peroxide) and NaOH (sodium hydroxide). This will yield cyclohexanol, where the OH group is added to the less substituted carbon of the double bond.
Step 3: To introduce the chlorine atom, perform a substitution reaction. React cyclohexanol with thionyl chloride (SOCl2) or phosphorus trichloride (PCl3) to replace the hydroxyl group with a chlorine atom, forming cyclohexyl chloride.
Step 4: To add the hydroxyl group back to the molecule, perform a nucleophilic substitution reaction. React cyclohexyl chloride with aqueous NaOH or KOH under controlled conditions to form the desired compound with both OH and Cl groups.
Step 5: Ensure the final product matches the target compound structure, with the hydroxyl group and chlorine atom attached to adjacent carbons on the cyclohexane ring.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
1mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Addition Reactions
Electrophilic addition reactions involve the addition of electrophiles to nucleophilic sites in alkenes. In the case of methylenecyclohexane, the double bond acts as a nucleophile, allowing for the addition of halogens or other electrophiles. This is a fundamental reaction in organic chemistry that can lead to the formation of various functional groups, such as halohydrins.
Recommended video:
Guided course
05:39
Features of Addition Mechanisms.
Halohydrin Formation
Halohydrins are compounds that contain both a halogen and a hydroxyl group on adjacent carbon atoms. The synthesis of halohydrins from alkenes typically occurs through the reaction of alkenes with halogens in the presence of water. Understanding this process is crucial for synthesizing the halohydrin compound shown in the question, as it illustrates how functional groups can be introduced to a carbon framework.
Recommended video:
Guided course
01:44General properties of halohydrin formation.
Regioselectivity and Stereochemistry
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry deals with the spatial arrangement of atoms in molecules. In the synthesis of halohydrins from methylenecyclohexane, it is important to consider which carbon atoms the halogen and hydroxyl group will attach to, as well as the potential for different stereoisomers to form, impacting the final product's properties.
Recommended video:
1:38Polymer Stereochemistry Concept 1
Related Practice
Textbook Question
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(g)
966
views
Textbook Question
Show what products you would expect from the following metathesis reactions, using the Schrock or Grubbs catalysts.
(b)
696
views
Textbook Question
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(i)
1251
views
Textbook Question
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(f)
1068
views
Textbook Question
Show how you would synthesize each compound using methylenecyclohexane as your starting material.
(e)
772
views