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Rank the following compounds in order of increasing acidity. a. \(\mathrm{NH}_{3}, \mathrm{H}_{2} \mathrm{O}, \mathrm{HF}\) e. \(\mathrm{CH}_{3} \mathrm{OH}, \mathrm{CH}_{3} \mathrm{NH}_{2}, \mathrm{CH}_{3} \mathrm{CH}_{3}\) b. \(\mathrm{HBr}, \mathrm{HCl}, \mathrm{HF}\) f. \(\mathrm{HCl}, \mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{2} \mathrm{~S}\) c. \(\mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{3} \mathrm{O}^{+}, \mathrm{HO}^{-}\) g. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{3}, \mathrm{CICH}_{2} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) d. \(\mathrm{NH}_{3}, \mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{2} \mathrm{~S}\) h. \(\mathrm{HC} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{3}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}, \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\)

Step by step solution

01

Analyzing Compound Groups

Start by analyzing each group's compounds based on their functional groups, electronegativity, and stability of their conjugate base, as these influence acidity.

02

Ranking Group a

In group a, we have NH鈧�, H鈧侽, and HF. HF is the most acidic due to the high electronegativity of fluorine which stabilizes the conjugate base. H鈧侽 is next, as oxygen is less electronegative than fluorine. NH鈧� is the least acidic.

03

Ranking Group b

The group b compounds are HBr, HCl, and HF. Acidity increases with the size of the halogen: HBr > HCl > HF, because larger anions are better at stabilizing the negative charge in the conjugate base.

04

Ranking Group c

For group c, we have H鈧侽, H鈧僌鈦�, and HO鈦�. H鈧僌鈦� is the most acidic as it donates a proton readily, followed by H鈧侽. HO鈦� is a base, not acidic, so it's the least acidic.

05

Ranking Group d

The compounds in group d are NH鈧�, H鈧侽, and H鈧係. H鈧係 is more acidic than H鈧侽 due to sulfur's larger size and weaker bond strength with hydrogen. NH鈧� is the least acidic.

06

Ranking Group e

In group e, we have CH鈧僌H, CH鈧僋H鈧�, and CH鈧僀H鈧�. CH鈧僌H is the most acidic as the alcohol can donate a proton. CH鈧僋H鈧� is next due to the nitrogen atom's basic nature. CH鈧僀H鈧� is the least acidic.

07

Ranking Group f

For group f, rank HCl, H鈧侽, and H鈧係 based on size and electronegativity. HCl is the most acidic, followed by H鈧係 (larger atom size), and H鈧侽 is the least acidic.

08

Ranking Group g

Group g contains CH鈧僀H鈧侰H鈧�, CICH鈧侰H鈧侽H, and CH鈧僀H鈧侽H. CICH鈧侰H鈧侽H is most acidic due to the electron-withdrawing chlorine. CH鈧僀H鈧侽H is next since it is an alcohol. CH鈧僀H鈧侰H鈧� is least acidic.

09

Ranking Group h

In group h, consider HC鈮�CCH鈧侰H鈧�, CH鈧僀H鈧侰H鈧侰H鈧�, and CH鈧僀H=CHCH鈧�. Acetylene (HC鈮�CCH鈧侰H鈧�) is most acidic because of the sp-hybridized carbon. CH鈧僀H=CHCH鈧� (alkene) is next. Saturated alkane (CH鈧僀H鈧侰H鈧侰H鈧�) is the least acidic.

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Key Concepts

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

Functional Groups

Functional groups are specific atoms or groups of atoms in a molecule that are responsible for its characteristic chemical reactions. Understanding the role of functional groups is crucial in predicting the acidity of compounds. By pinpointing these groups, we can infer how the compound behaves in acid-base chemistry.
Functional groups like alcohols (鈥揙H), amines (鈥揘H鈧�), and halides (鈥揦) greatly influence acidity.

• Alcohols, due to the hydroxyl group, can lose a proton and thus display acidic properties.
• Amines contain the slightly basic amino group which usually makes the compound less acidic.
• Halides, especially those containing fluorine, chlorine, or bromine, increase acidity due to their high electronegativity.

Identifying these groups allows chemists to determine potential proton donors, which defines an acid in acid-base reactions.

Electronegativity

Electronegativity is how strongly an atom attracts electrons in a covalent bond.
It's a crucial factor that impacts acidity.
In general, the more electronegative an atom is, the better it can stabilize a negative charge.

• When evaluating acidity, electronegativity can help you identify which compound will most likely donate a proton.
• Compounds like hydrogen fluoride (HF) are highly acidic due to fluorine's high electronegativity.
• The high electronegativity translates to stronger pull on electrons, stabilizing the conjugate base better once the proton is lost.

Thus, electronegativity offers insight into the strength of attraction between atoms, predicting how readily they will donate a proton.

Conjugate Base Stability

Conjugate base stability is one of the key determinants of a compound's acidity.
When an acid donates a proton, what remains is its conjugate base.
The more stable this conjugate base, the stronger the corresponding acid.

• Larger ions, such as bromide in HBr, stabilize by spreading the negative charge over a larger volume.
• Anions formed from more electronegative atoms like fluorine also stabilize the negative charge effectively due to their ample electron-attracting power.
• Delocalization of the negative charge through resonance in the conjugate base also stabilizes it, enhancing acidity.

Understanding conjugate base stability helps in ranking acids, as a clearer insight into why certain compounds are more acidic becomes evident.

Acid-Base Chemistry

Acid-base chemistry revolves around the transfer of protons (H鈦� ions) between molecules.
Acids donate protons, while bases accept them.
The behavior of compounds in acid-base reactions is predicted largely by analyzing their functional groups, electronegativity, and conjugate base stability.

• Understanding the role of these factors helps predict and interpret how compounds will interact in chemical reactions.
• In practical terms, ranking compounds by acidity means understanding how easily they donate protons.
• This can be valuable in a variety of chemical applications including synthesis and reaction prediction.

Overall, immersion in the principles of acid-base chemistry brings clarity to the questions of why certain compounds rank higher in acidity.