Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 2.8, Problem 35P

(a)

Interpretation Introduction

Interpretation:

The resonance contributors for given species has to be drawn.

Concept Introduction:

Localized electrons:

If the negative charge formed by losing a proton resides only on one atom, they are termed as localized electrons.  For example, if an alcohol loses a proton, the electrons remaining will be resides on its single oxygen atom.

Delocalized electrons:

If the negative charge formed by losing a proton resides on more than two atoms, they are termed as delocalized electrons.  For example, if carboxylic acid loses a proton, the electrons remaining will be resides on both oxygen atoms and thus reduces the electron density of the atom making the conjugate base more stable.

Organic Chemistry (8th Edition), Chapter 2.8, Problem 35P , additional homework tip  1

The above two structures are known as resonance contributors and the actual structure which is called the resonance hybrid will be the composite of the two resonance contributors.

(b)

Interpretation Introduction

Interpretation:

The resonance contributors for given species has to be drawn.

Concept Introduction:

Localized electrons:

If the negative charge formed by losing a proton resides only on one atom, they are termed as localized electrons.  For example, if an alcohol loses a proton, the electrons remaining will be resides on its single oxygen atom.

Delocalized electrons:

If the negative charge formed by losing a proton resides on more than two atoms, they are termed as delocalized electrons.  For example, if carboxylic acid loses a proton, the electrons remaining will be resides on both oxygen atoms and thus reduces the electron density of the atom making the conjugate base more stable.

Organic Chemistry (8th Edition), Chapter 2.8, Problem 35P , additional homework tip  2

The above two structures are known as resonance contributors and the actual structure which is called the resonance hybrid will be the composite of the two resonance contributors.

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Chapter 2 Solutions

Organic Chemistry (8th Edition)

Ch. 2.3 - a. Write an equation showing CH3OH reacting as an...Ch. 2.3 - Estimate the pKa values of the following...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. 15PCh. 2.5 - a. For each of the acid-base reactions in Section...Ch. 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. 2.5 - Calculate the equilibrium constant for the...Ch. 2.6 - Rank the ions (CH3, NH2, HO, and F) from most...Ch. 2.6 - Rank the carbanions shown in the margin from most...Ch. 2.6 - Which is the stronger acid?Ch. 2.6 - Prob. 23PCh. 2.6 - What reaction in Problem 23 has the smallest...Ch. 2.6 - Rank the halide ions (F, Cl, Br, and l) from...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 l) is...Ch. 2.6 - Which is a stronger base? (The potential maps in...Ch. 2.7 - What is a stronger acid? a. CH3OCH2CH2OH or...Ch. 2.7 - Rank the following compounds from strongest add to...Ch. 2.7 - What is a stronger base?Ch. 2.8 - For each of the following compounds, indicate the...Ch. 2.8 - Prob. 35PCh. 2.8 - Which is a stronger acid? Why?Ch. 2.8 - Fosamax (shown on the previous page) has six...Ch. 2.9 - Using the table of pKa values given in Appendix I,...Ch. 2.10 - For each of the following compounds (here shown in...Ch. 2.10 - As long as the pH is not less than _______, at...Ch. 2.10 - a. Indicate whether a protonated amine (RN+H3)...Ch. 2.10 - A naturally occurring amino acid such as alanine...Ch. 2.10 - a. At what pH is the concentration of a compound,...Ch. 2.10 - For each of the following compounds, indicate the...Ch. 2.10 - Given the data in Problem 47: a. What pH would you...Ch. 2.11 - Write the equation that shows how a buffer made by...Ch. 2.12 - Draw the products of the following react ions. Use...Ch. 2.12 - What product are formed when each of the following...Ch. 2 - Which is a stronger base? a. HS or HO b. CH3O or...Ch. 2 - According to the explanations by Lewis, if a...Ch. 2 - a. Rank the following alcohols from strongest to...Ch. 2 - a. Rank the following carboxylic acids from...Ch. 2 - Prob. 57PCh. 2 - For the following compound. a. draw its conjugate...Ch. 2 - Rank the following compounds from strongest to...Ch. 2 - Prob. 60PCh. 2 - Prob. 61PCh. 2 - a. Rank the following alcohols from strongest to...Ch. 2 - A single bond between two carbons with different...Ch. 2 - For each compound, indicate the atom that is most...Ch. 2 - a. Given the Ka values, estimate the pKa value of...Ch. 2 - Tenormin, a member of the group of drugs known as...Ch. 2 - From which of the following compounds can HO...Ch. 2 - a. For each of the following pairs of reactions,...Ch. 2 - Prob. 69PCh. 2 - Which is a stronger acid? a. b. c. d.Ch. 2 - Prob. 71PCh. 2 - Prob. 72PCh. 2 - Given that pH+ pOH = 14 and that the concentration...Ch. 2 - How could you separate a mixture of the following...Ch. 2 - Prob. 75PCh. 2 - a. If an add with a pKa of 5.3 is in an aqueous...Ch. 2 - Calculate the pH values of the following...Ch. 2 - Prob. 1PCh. 2 - Prob. 2PCh. 2 - Prob. 3PCh. 2 - Which of the reactions in Problem 3 favor...Ch. 2 - Prob. 5PCh. 2 - Prob. 6PCh. 2 - Prob. 7PCh. 2 - Which is the stronger acid? a. ClCH2CH2OH or...Ch. 2 - Prob. 9PCh. 2 - Prob. 10PCh. 2 - Which is a more stable base? Remembering that the...Ch. 2 - Which is the Stronger acid?Ch. 2 - Prob. 13PCh. 2 - a. Draw the structure of (CH3COOH (pKa = 4.7) at...
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