교과서 질문
Write structural formulas for the following compounds (includes both old- and new-style names).
(d) cyclohexylacetylene
(e) 5-methyl-3-octyne
(f) trans-3,5-dibromocyclodecyne
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Ch.9 - Alkynes
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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TOC.tableOfContents
- 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
9장, 문제 25a
Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.
(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)
검증된 단계별 안내1
Step 1: Begin by identifying the target molecule, 3-methylnon-4-yn-3-ol. This molecule contains a triple bond at carbon 4, a methyl group at carbon 3, and a hydroxyl group (-OH) also at carbon 3. The chain is nine carbons long. Acetylene (C₂H₂) will serve as the starting material, and you are limited to compounds with no more than four carbons.
Step 2: Use acetylene as the base to construct the carbon chain. Perform successive alkylation reactions to elongate the chain. First, convert acetylene into an acetylide ion (C≡C⁻) using a strong base such as NaNH₂. Then, react the acetylide ion with an appropriate alkyl halide (e.g., CH₃CH₂Br) to add two carbons to the chain, forming a propyne derivative.
Step 3: Continue chain elongation by repeating the alkylation process. Generate another acetylide ion from the propyne derivative and react it with another alkyl halide (e.g., CH₃CH₂CH₂Br) to add three more carbons, forming a heptyne derivative. Ensure the triple bond remains intact at carbon 4.
Step 4: Introduce the methyl group at carbon 3. Use a Grignard reagent (e.g., CH₃MgBr) to add the methyl group to the heptyne derivative. This step requires careful control to ensure the methyl group is added specifically at carbon 3.
Step 5: Add the hydroxyl group (-OH) at carbon 3. Perform a hydroboration-oxidation reaction using reagents such as BH₃ followed by H₂O₂/NaOH. This reaction will selectively add the hydroxyl group to the desired position, completing the synthesis of 3-methylnon-4-yn-3-ol.
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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
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주요 개념
질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.
Acetylene as a Building Block
Acetylene (C2H2) is a simple alkyne that serves as a versatile building block in organic synthesis. Its triple bond allows for various reactions, including addition reactions with electrophiles, which can lead to the formation of longer carbon chains. Understanding how to manipulate acetylene in reactions is crucial for constructing more complex molecules, such as the target compound in the question.
추천 영상:
16:59
Building a molecular sentence
Functional Groups and Their Importance
Functional groups are specific groups of atoms within molecules that determine the chemical reactivity and properties of those molecules. In the case of 3-methylnon-4-yn-3-ol, the presence of the hydroxyl group (-OH) indicates that the compound is an alcohol, which influences its reactivity and the types of reactions it can undergo. Recognizing and utilizing functional groups is essential for designing synthetic pathways.
추천 영상:
02:36Identifying Functional Groups
Carbon Chain Length and Structure
The structure and length of carbon chains are fundamental in organic chemistry, as they dictate the physical and chemical properties of compounds. The target compound, 3-methylnon-4-yn-3-ol, has a specific carbon skeleton that must be constructed using starting materials with no more than four carbon atoms. Understanding how to build and modify carbon chains is key to successful synthesis.
추천 영상:
01:53Learning Alkane Prefixes up to 12 Carbons in Length
관련 실천
교과서 질문
Write structural formulas for the following compounds (includes both old- and new-style names).
(a) 2-octyne
(b) ethylisopentylacetylene
(c) ethynylbenzene
1519
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교과서 질문
Predict the product(s) you would expect from treatment of each compound with (1) dilute, neutral KMnO4 and (2) warm basic KMnO4, then dilute acid.
(e) cyclodecyne
778
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교과서 질문
Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.
(b) An unknown alkyne undergoes oxidative cleavage to give the following triacid plus one equivalent of propionic acid. Propose a structure for the alkyne.
1200
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교과서 질문
Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.
(b) cis-1-ethyl-2-methylcyclopropane
637
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교과서 질문
Oxidative cleavages can help to determine the positions of the triple bonds in alkynes.
(a) An unknown alkyne undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid. Propose a structure for the alkyne.
1250
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