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Among the following compounds, the strongest acid is: (a) \(\mathrm{HC} \equiv \mathrm{CH}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{6}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{6}\) (d) \(\mathrm{CH}_{3} \mathrm{OH}\)

Short Answer

Expert verified
The strongest acid is (d) CH鈧僌H (methanol).

Step by step solution

01

Understand Acid Strength

Acid strength is determined by the molecule's ability to donate a proton (H鈦). The more easily a compound can donate a proton, the stronger the acid.
02

Analyze Each Compound

Consider the acidity of each compound: (a) HC鈮H (acetylene) has a relatively strong C-H bond, making it less acidic. (b) C鈧咹鈧 (benzene) is a stable aromatic compound and doesn't donate protons easily. (c) C鈧侶鈧 (ethane) has only single C-H bonds, making it quite neutral and a very weak acid. (d) CH鈧僌H (methanol) contains an O-H bond, which can donate a proton and behave as an acid.
03

Comparison of Acidities

Compare the compounds: - C鈧侶鈧 is the weakest as it is a typical alkane with very low acidity. - C鈧咹鈧 is also quite weak due to its aromatic stability. - HC鈮H is more acidic than C鈧侶鈧 and C鈧咹鈧 due to the sp-hybridized carbon. - CH鈧僌H, with the presence of an O-H group, is capable of donating a proton more effectively than the C-H bonds in the other compounds.
04

Conclude on the Strongest Acid

Based on the ability to donate protons, CH鈧僌H is the strongest acid among the four options because it contains the O-H group, which is more acidic than the C-H bonds in the other molecules.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Proton Donation
In organic chemistry, the concept of proton donation is central to understanding acid strength. An acid's strength is gauged by its ability to donate a proton, denoted as - When an acid donates - the conjugate base forms from the remaining part of the molecule Proton donation is facilitated by the molecule's structure and the bond strength holding the The weaker the bond, the easier it is for the molecule to release its hydrogen as a proton, hence the stronger the acid Strong acids are characterized by the ability to donate protons readily, often influenced by factors such as electronegativity of the atom to which the hydrogen is bonded and the stability of the conjugate base formed.
C-H Bond Acidity
The acidity associated with C-H bonds varies considerably across organic compounds. C-H bonds are typically weaker acids compared to bonds involving more electronegative atoms, such as oxygen in - The nature of the carbon hybridization in a C-H bond impacts the acidity: sp-hybridized carbons are more acidic compared to sp2 and sp3 hybridized carbons due to higher - For instance, acetylene ( HC鈮H) has an This allows acetylene to exhibit relatively higher acidity among hydrocarbons, although it is still weaker than acids with O-H bonds In contrast, compounds like ethane with only sp3 C-H bonds are notably poor acids. This is due to the relatively low electronegativity and hybridization, leading to minimal proton donation capability.
O-H Bond Acidity
O-H bonds in organic compounds are typically more acidic than C-H bonds due to the higher electronegativity of Electronegativity refers to the tendency of an atom to attract electrons towards itself, making O-H bonds susceptible to proton donation Consider methanol (CH鈧僌H), where the O-H bond can readily release a proton, forming - The presence of an electronegative oxygen stabilizes the conjugate base (CH鈧僌鈦), enhancing acidity - Additionally, the ability of oxygen to accommodate negative charge strengthens the O-H acidity relative to C-H bonds found in hydrocarbons Thus, the presence of an O-H bond generally indicates a superior capacity for proton donation, leading to greater acidity in organic compounds.
Organic Chemistry Acidity Comparison
Comparing acid strength involves evaluating a compound's ability to donate protons across different types of - alkanes, such as ethane, are very weak acids because their C-H bonds do not easily release protons - Aromatic compounds like benzene are also weak acids; although stable, they typically lack the readiness to donate - Acetylene, due to its sp-hybridization, displays moderate acidity in contrast to ethane or benzene Finally, methanol represents the strongest acid in the group due to its O-H bond, which allows for effective proton donation When acidities of organic compounds are compared, the general trend is as follows: - O-H bonds tend to be more acidic than C-H bonds - The nature of the bonding, hybridization, and atom electronegativity all contribute to acid strength in organic chemistry. This hierarchy underscores why methanol is considered the strongest acid among the provided compounds.

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Most popular questions from this chapter

Among the following compounds which has more than one type of hybridization for carbon atom? 1\. \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CH}_{3}\) 2\. \(\mathrm{CH}_{3}-\mathrm{CH}^{2}=\mathrm{CH}-\mathrm{CH}_{3}\) 3\. \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{C} \equiv \mathrm{CH}\) 4\. \(\mathrm{CH}_{2}=\mathrm{CH}_{2}\) (a) 2 only (b) 2 and 3 (c) 1 and 3 (d) 3 and 4

Cyclooctatetraene is not aromatic. The most important reason for this is that: (a) It is a planar molecule (b) It has eight \(\pi\) -electrons (c) Its structure cannot be described by more than the canonical forms (d) Its structure is not that of regular octagon

\(18 \mathrm{C}-\mathrm{H}\) and \(7 \mathrm{C}-\mathrm{C}\) sigma bonds are present in: (a) n-heptane (b) Cyclohexane (c) 3,3 -dimethyl pentane (d) \(2,2,3\) -trimethyl pentane

A hydrocarbon \(\mathrm{C}_{6} \mathrm{H}_{10}\) does not react with ammonical solution of \(\mathrm{Cu}^{+}\) ions; it adsorbs \(2 \mathrm{~mol}\) of hydrogen on catalytic hydrogenation to give 2 -methylpentane. The hydrocarbon adds one molecule of water on treatment with \(\mathrm{Hg}^{2+} / \mathrm{H}_{2} \mathrm{SO}_{4}\). The structure of given compound is: (a) \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\) (b) \(\mathrm{H}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) (c) C=CCC(C)C=C (d) \(\mathrm{HC} \equiv \mathrm{C}-\mathrm{CH}_{2}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\)

The treatment of benzene with isobutene in the presence of sulphuric acid gives: (a) Isobutyl benzene (b) n-butyl benzene (c) tert-butyl benzene (d) Cumene

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