EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 2, Problem 10P

(a)

Interpretation Introduction

Interpretation:

The more stable base between Br and I has to be identified.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Size affecting the stability of the base: In order to determine the strength of the base, the size of an atom overrides electronegativity. As the atoms get larger and the stability of the anions increases even though the electronegativity of the atoms decreases. Stability of the bases increases going down the group. Stable bases are weak bases.

(b)

Interpretation Introduction

Interpretation:

 The more stable base between CH3O and CH3S has to be identified.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Size affecting the stability of the base: In order to determine the strength of the base, the size of an atom overrides electronegativity. As the atoms get larger and the stability of the anions increases even though the electronegativity of the atoms decreases. Stability of the bases increases going down the group. Stable bases are weak bases.

(c)

Interpretation Introduction

Interpretation:

The more stable base between CH3CH2O-  and CH3COO- has to be identified.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Electronegativity: The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Electronegativity depends on the acidity of a species. Order of electronegativity of hybridization is sp>sp2>sp3 so sp3 hybridized molecule is weak acid.

Effect of electron delocalization: if a base has localized electrons, then the negative charge that results when the base’s conjugate acid loses a proton will belong to one atom.

A base with delocalized electron is more stable than a similar base with localized electrons.

(d)

Interpretation Introduction

Interpretation:

The more stable base between H2C=CH and HCC has to be identified.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Electronegativity: The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Effect of Hybridization: Electronegativity depends on the acidity of a species. Order of electronegativity of hybridization is sp>sp2>sp3 so sp3 hybridized molecule is weak acid.

(e)

Interpretation Introduction

Interpretation:

The more stable base between FCH2CH2COO and BrCH2CH2COO has to be identified.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Electronegativity: The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Effect of Inductive electron withdrawal on Acidity: Replacing a Hydrogen with an electronegative substituent pulls bonding electrons toward itself; increases the strength of the acid.

(f)

Interpretation Introduction

Interpretation:

The more stable base between ClCH2CH2O and ClCHCH2O has to be identified.

Concept introduction:

If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.

If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.

Electronegativity: The chemical behavior of an atom where it attracts the shared electron pair to itself. Down the group, electronegativity decreases as the number of energy levels increases.

Effect of Inductive electron withdrawal on Acidity: Replacing a Hydrogen with an electronegative substituent pulls bonding electrons toward itself; increases the strength of the acid.

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Chapter 2 Solutions

EBK ESSENTIAL ORGANIC CHEMISTRY

Ch. 2.3 - a. Which is a stronger base, CH3COO or HCOO? (The...Ch. 2.3 - Using the pKa values in Section 2.3, rank the...Ch. 2.4 - Prob. 13PCh. 2.5 - Prob. 14PCh. 2.5 - Ethyne has a pKa value of 25, water has a pKa...Ch. 2.5 - Which of the following bases can remove a proton...Ch. 2.6 - List the ions (CH3, NH2, HO, and F) in order from...Ch. 2.6 - List the carbanions shown in the margin in order...Ch. 2.6 - Which is a stronger acid?Ch. 2.6 - a. Draw the products of the following reactions: A...Ch. 2.6 - List the halide ions (F, Cl, Br, and I) in order...Ch. 2.6 - a. Which is more electronegative, oxygen or...Ch. 2.6 - Which is a stronger acid? a. HCl or HBr b....Ch. 2.6 - a. Which of the halide ions (F, Cl, Br, and I) is...Ch. 2.6 - Which is a stronger base? a. H2O or HO b. H2O or...Ch. 2.7 - Which is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Which is a stronger base?Ch. 2.8 - Fosamax has six acidic groups. The structure of...Ch. 2.8 - Which is a stronger acid? Why?Ch. 2.10 - For each of the following compounds (shown in...Ch. 2.10 - Prob. 33PCh. 2.11 - Write the equation that shows how a buffer made by...Ch. 2.11 - What products are formed when each of the...Ch. 2 - a. List the following alcohols in order from...Ch. 2 - Which is a stronger base? a. HS or HO b. CH3O or...Ch. 2 - Prob. 40PCh. 2 - a. List the following carboxylic acids in order...Ch. 2 - For the following compound, a. draw its conjugate...Ch. 2 - List the following compounds in order from...Ch. 2 - For each of the following compounds, draw the form...Ch. 2 - Give the products of the following acidbase...Ch. 2 - Prob. 46PCh. 2 - For each compound, indicate the atom that is most...Ch. 2 - Tenormin, a member of the group of drugs known as...Ch. 2 - From which acids can HO remove a proton in a...Ch. 2 - Prob. 50PCh. 2 - Which is a stronger acid? a. CH29CHCOOH or...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 1PCh. 2 - Prob. 2PCh. 2 - Draw the products of the following acidbase...Ch. 2 - Prob. 4PCh. 2 - Prob. 5PCh. 2 - Prob. 6PCh. 2 - Prob. 7PCh. 2 - Prob. 8PCh. 2 - Prob. 9PCh. 2 - Prob. 10PCh. 2 - Prob. 11PCh. 2 - Prob. 12PCh. 2 - Prob. 13PCh. 2 - Prob. 14P
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