Which is a stronger acid? c. CH 3 OCH 2 CH 2 CH 2 OHorCH 3 CH 2 OCH 2 CH 2 OH d.

Hey, everyone and welcome back, identify the stronger acid in each pair. Starting with a the best idea is to draw these structures in their bond line representation. So we have three carbon atoms bonded to oxygen, then we have two more carbon atoms and then we have no age group. And the second structure corresponds to two carbon atoms bonded to oxygen, three carbon atoms bonded to O H. In these two structures, we are going to define the most acidic hydrogen which is directly bonded to oxygen. And we will notice that in the first structure, the O H group is two carbons away from the ether oxygen. And then the second structure, the oh age group is three carbon atoms away from the ether oxygen. The reason why this is important is because oxygen is strongly electro negative. So it's withdrawing the electron density from our chain towards itself in each case. So the arrows illustrate how electrons flow towards oxygen. And this is really relevant for us because that electron flow allows us to polarize the O H bond in each case. And the greater the polarized ability of that bond or basically the more polarized that O H bond becomes the easier it is for us to break it and release our hydrogen in the form of an acidic protein into a solution. So, in the first structure that oxygen, because it's closer to wage, only two carbons away, it's basically exerting a greater electron withdrawing effect on O H and weakening the O H bond better. That means the first structure is a stronger acid while the second one is weaker because oxygen is three carbons away and it's not so efficient in electron withdrawing, being further away from a wage, right? So this is our answer to part A. And if you look at part B, we identify our city high genes that are bonded to oxygen directly. And we may recall that the carbon group that is present in each of these structures is electron withdrawing similarly to what we did before we noticed that carbon group is one carbon away from the O H group. And then the second one is two carbon atoms away because the distance between the electron withdrawing carbon and the wage group is lower in the first structure. It must be a stronger asset. The second one is weaker because Carbonell is further away from a wage to carbon atoms away instead of one. And the reason is exactly the same if Carbonell group is closer to h it has a greater electron withdrawing effect on weakening that O H bond and making it more polarized so that the hydrogen atom can be released into a solution in the form of an acidic proton. So let's summarize our answers for party Structure. Number one is more acidic and for B Also structure # one is more acidic based on these answers. D is the correct choice for the small vultures question. Thank you for. Thank you for watching.

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1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

3. Acids and Bases

Ranking Acidity

Organic Chemistry

3. Acids and Bases

Ranking Acidity

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3:58 minutes

Problem 30c,d

Textbook Question

Which is a stronger acid?
c. CH₃OCH₂CH₂CH₂OHorCH₃CH₂OCH₂CH₂OH
d.

Verified step by step guidance

Step 1: Analyze the molecular structures provided in the image. Both compounds (i) and (ii) are carboxylic acids, but they differ in the position of the hydroxyl group (-OH) relative to the carbonyl group (C=O). In (i), the hydroxyl group is on the second carbon, while in (ii), it is on the third carbon.

Step 2: Understand the concept of inductive effects. Electronegative groups like the hydroxyl group (-OH) can withdraw electron density through sigma bonds, stabilizing the conjugate base of the acid and increasing its acidity. The closer the electronegative group is to the acidic proton, the stronger the inductive effect.

Step 3: Compare the proximity of the hydroxyl group to the carboxylic acid functional group in both molecules. In compound (i), the hydroxyl group is closer to the carboxylic acid group, which means it will exert a stronger inductive effect compared to compound (ii).

Step 4: Predict the relative acidity based on the inductive effect. Since the hydroxyl group in compound (i) is closer to the acidic proton, it will stabilize the conjugate base more effectively, making compound (i) a stronger acid than compound (ii).

Step 5: Conclude that the position of the hydroxyl group significantly influences the acidity of the molecule due to the inductive effect. Compound (i) is the stronger acid compared to compound (ii).

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acidity and pKa

Acidity in organic chemistry is often measured by the pKa value, which indicates the strength of an acid. A lower pKa value corresponds to a stronger acid, meaning it can donate protons (H+) more readily. Understanding the relationship between structure and acidity is crucial, as factors like electronegativity and resonance can significantly influence pKa values.

Inductive Effect

The inductive effect refers to the electron-withdrawing or electron-donating influence of substituents on a molecule. Electronegative atoms or groups can stabilize the negative charge on the conjugate base of an acid, enhancing its acidity. In the comparison of acids, the presence of electron-withdrawing groups can lead to increased acidity due to this effect.

Resonance Stabilization

Resonance stabilization occurs when a molecule can be represented by multiple valid Lewis structures, allowing for the delocalization of electrons. This delocalization can stabilize the conjugate base formed after an acid donates a proton, making the original acid stronger. Analyzing the structures of the compounds in the question will reveal how resonance affects their acidity.

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