Phenol is considerably stronger acid than cyclohexanol; the reason has to be proposed. Concept Introduction: Base and its conjugate Acid: A Base is a species that can gain a proton. When a base gains a proton ( H + ) , it forms its conjugate acid. In order to gain a proton, a base must possess lone pair that it can use to form a new bond with the proton. Neutral base forms a positively charged conjugate acid, whereas a positively charged base forms a neutral conjugate acid. Electron delocalization stabilizes base: If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will belong to one atom. If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will be shared by two or more atoms. A base with delocalized electron is more stable than a similar base with localized electrons. Effect of hybridization on Acidity: The electronegativity of an atom depends on its hybridization. The stronger acid will have its proton attached to the more electronegative atom.

Question

b) Certain cyclic compounds are known to be conformationally similar to carbohydrates, although they are not themselves carbohydrates. One example is Compound C shown below, which could be imagined as adopting four possible conformations. In reality, however, only one of these is particularly stable. Circle the conformation you expect to be the most stable, and provide an explanation to justify your choice. For your explanation to be both convincing and correct, it must contain not only words, but also "cartoon" orbital drawings contrasting the four structures. Compound C Possible conformations (circle one): Дет

Answer 1

Question

Chapter 10, Problem 10.49P

Interpretation Introduction

Interpretation:

Phenol is considerably stronger acid than cyclohexanol; the reason has to be proposed.

Concept Introduction:

Base and its conjugate Acid: A Base is a species that can gain a proton. When a base gains a proton (H+), it forms its conjugate acid. In order to gain a proton, a base must possess lone pair that it can use to form a new bond with the proton. Neutral base forms a positively charged conjugate acid, whereas a positively charged base forms a neutral conjugate acid.

Electron delocalization stabilizes base: If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will belong to one atom. If a base has delocalized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will be shared by two or more atoms. A base with delocalized electron is more stable than a similar base with localized electrons.

Effect of hybridization on Acidity: The electronegativity of an atom depends on its hybridization.

The stronger acid will have its proton attached to the more electronegative atom.

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