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Ch.10 - Structure and Synthesis of Alcohols
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh.10 - Structure and Synthesis of Alcohols문제 33a,b
10장, 문제 33a,b

Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.
a. hexan-1-ol or 3,3-dimethylbutan-1-ol
b. hexan-2-one or hexan-2-ol

검증된 단계별 안내
1
Step 1: Understand the factors affecting boiling points. Boiling points are influenced by intermolecular forces such as hydrogen bonding, dipole-dipole interactions, and London dispersion forces. Molecules with stronger intermolecular forces generally have higher boiling points.
Step 2: Analyze (a) hexan-1-ol vs. 3,3-dimethylbutan-1-ol. Both are alcohols, meaning they can form hydrogen bonds due to the presence of the hydroxyl (-OH) group. However, hexan-1-ol has a straight-chain structure, which allows for stronger London dispersion forces compared to the branched structure of 3,3-dimethylbutan-1-ol. Branching reduces the surface area available for intermolecular interactions, lowering the boiling point.
Step 3: Analyze (b) hexan-2-one vs. hexan-2-ol. Hexan-2-one is a ketone, which can only exhibit dipole-dipole interactions due to the polar carbonyl group. Hexan-2-ol, on the other hand, is an alcohol and can form hydrogen bonds in addition to dipole-dipole interactions. Hydrogen bonding is significantly stronger than dipole-dipole interactions, so hexan-2-ol is expected to have a higher boiling point.
Step 4: Compare molecular weights and structures. Both pairs of compounds have similar molecular weights, so the differences in boiling points are primarily due to the types and strengths of intermolecular forces rather than size.
Step 5: Summarize the predictions. For (a), hexan-1-ol is predicted to have a higher boiling point due to its straight-chain structure and stronger London dispersion forces. For (b), hexan-2-ol is predicted to have a higher boiling point due to the presence of hydrogen bonding, which is stronger than the dipole-dipole interactions in hexan-2-one.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
7m

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Hydrogen Bonding

Hydrogen bonding is a strong type of dipole-dipole interaction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen or nitrogen. In alcohols, the presence of an -OH group allows for hydrogen bonding between molecules, significantly increasing their boiling points compared to hydrocarbons of similar molecular weight, which lack such interactions.
추천 영상:
00:48
The definition of hydrogenation.

Molecular Structure and Steric Hindrance

Molecular structure refers to the arrangement of atoms within a molecule, which can influence physical properties like boiling point. Steric hindrance occurs when bulky groups around a functional group impede interactions, such as hydrogen bonding. In the case of 3,3-dimethylbutan-1-ol, the presence of two methyl groups near the -OH group reduces the ability to form hydrogen bonds compared to hexan-1-ol, leading to a lower boiling point.
추천 영상:
08:41
Review of Molecular Orbitals

Functional Groups and Polarity

Functional groups are specific groups of atoms within molecules that determine their chemical properties. The polarity of a molecule, influenced by its functional groups, affects its boiling point; polar molecules, like alcohols, generally have higher boiling points due to stronger intermolecular forces. In comparing hexan-2-one and hexan-2-ol, the alcohol's -OH group introduces polarity and hydrogen bonding, resulting in a higher boiling point than the ketone.
추천 영상:
02:36
Identifying Functional Groups
관련 실천
교과서 질문

Draw the structures of the following compounds. (Includes both new and old names.)

(k) 3-methylhex-4-yn-2-ol

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교과서 질문

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

b. cyclohexanol or cyclohexanethiol

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교과서 질문

Predict which member of each group is most soluble in water, and explain the reasons for your predictions.

a. butan-1-ol, pentan-1-ol, or propan-2-ol

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교과서 질문

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

a. cyclopentanol or 3-chlorophenol

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교과서 질문

Draw the structures of the following compounds. (Includes both new and old names.)

i. cyclopent-3-ene-1-thiol

j. dimethyl disulfide

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교과서 질문

Draw the structures of the following compounds. (Includes both new and old names.)

(d) 3-cyclopentylhexan-3-ol

(e) meso-2,4-pentanediol

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