Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 2, Problem 2.10P
Estimate the pKa of each of the indicated bonds.
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Students have asked these similar questions
Which of the compounds have the lowest pKA, why?
The pka of phenol (C6H5OH) is 10.0. When a nitro group
(NO2) is attached to the ring, the pK, decreases, as shown
for the ortho, meta, and para isomers.
OH
OH
ОН
OH
NO2
(a) Explain why the pK, values of all three isomers are
lower than the pka of phenol itself.
(b) Explain why the meta isomer has the highest pka of
`NO2
Phenol
NO2
the three isomers.
pKa = 10.0
7.23
8.35
7.14
(a) What is the hybridization of the nitrogen in each of the following compounds? (b)
How does hybridization affect the availability of the lone pair and the basicity of each
compound?
N.
I
II
ZI E
Chapter 2 Solutions
Organic Chemistry
Ch. 2 - a. Which compounds are Bronsted-Lowry acids:...Ch. 2 - a. Draw the conjugate acid of each base:...Ch. 2 - Label the acid and base, and the conjugate acid...Ch. 2 - Draw the products of each proton transfer...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Which compound in each pair is the stronger acid?...Ch. 2 - Use a calculator when necessary to answer the...Ch. 2 - Rank the conjugate bases of each of group of acids...Ch. 2 - Problem-2.10 Considers two acids: (formic acid,)...Ch. 2 - Estimate the pKa of each of the indicated bonds.
Ch. 2 - Draw the products of each reaction and determine...Ch. 2 - Prob. 2.12PCh. 2 - Without reference to a pKa table, decide which...Ch. 2 - which compound in each pair of isomers is the...Ch. 2 - Prob. 2.15PCh. 2 - Which hydrogen in pseudoephedrine, the nasal...Ch. 2 - whichcompound in each pair is the stronger acid? a...Ch. 2 - Glycolic acid, HOCH2CO2H, is the simplest member...Ch. 2 - Explain the apparent paradox. HBr is a stronger...Ch. 2 - The CH bond in acetone, (CH3)2C=O, has a pKa of...Ch. 2 - Acetonitrile (CH3CN) has a pKa of 25, making it...Ch. 2 - For each pair of compounds: [1] Which indicated H...Ch. 2 - Rank the compounds in each group in order of...Ch. 2 - Which proton in each of the following drugs is...Ch. 2 - Prob. 2.25PCh. 2 - Problem 2.29
Compounds like amphetamine that...Ch. 2 - Problem 2.30 Which species are Lewis bases?
a. b....Ch. 2 - Which species are Lewis acids?
a. b. c. d.
Ch. 2 - For each reaction, label the Lewis acid and base....Ch. 2 - Prob. 2.30PCh. 2 - Prob. 2.31PCh. 2 - Prob. 2.32PCh. 2 - 2.36 Propranolol is an antihypertensive agent—that...Ch. 2 - 2.37 Amphetamine is a powerful stimulant of the...Ch. 2 - Prob. 2.35PCh. 2 - Prob. 2.36PCh. 2 - a Draw the conjugate acid of ethylene, CH2 = CH2....Ch. 2 - 2.40 Draw the products formed from the acid-base...Ch. 2 - Draw the products formed from the acid-base...Ch. 2 - Prob. 2.40PCh. 2 - Draw the product of acid-base reaction. a. c. b....Ch. 2 - Prob. 2.42PCh. 2 - Prob. 2.43PCh. 2 - What is Ka for each compound? Use a calculator...Ch. 2 - What is the pKa for each compound? a. b. c.Ch. 2 - Which of the following bases are strong enough to...Ch. 2 - Which compounds can be deprotonated by OH, so that...Ch. 2 - Draw the product of each reaction. Use the pKa...Ch. 2 - Rank the following compounds in order of...Ch. 2 - Rank the following ions in order of increasing...Ch. 2 - Prob. 2.51PCh. 2 - Prob. 2.52PCh. 2 - The pKa of three CH bonds is given below. a. For...Ch. 2 - a. What is the conjugate acid of A? b. What is the...Ch. 2 - 2.56 Draw the structure of a constitutional isomer...Ch. 2 - 2.57 Many drugs are Bronsted-Lowry acids or...Ch. 2 - Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH)...Ch. 2 - Prob. 2.58PCh. 2 - Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the...Ch. 2 - Prob. 2.60PCh. 2 - 2.61 Label the three most acidic hydrogen atoms in...Ch. 2 - Prob. 2.62PCh. 2 - 2.64 Classify each species as a Lewis acid, a...Ch. 2 - Prob. 2.64PCh. 2 - Draw the products of each Lewis acid-base...Ch. 2 - Prob. 2.66PCh. 2 - Prob. 2.67PCh. 2 - 2.70 Hydroxide can react as a Brønsted-Lowry base...Ch. 2 - 2.71 Answer the following questions about esmolol,...Ch. 2 - Prob. 2.70PCh. 2 - 2.72 DBU, is a base we will encounter in...Ch. 2 - 2.73 Molecules like acetamide can be protonated...Ch. 2 - Two pKa values are reported for malonic acid, a...Ch. 2 - Prob. 2.74PCh. 2 - 2.76 Write a stepwise reaction sequence using...Ch. 2 - Prob. 2.76PCh. 2 - 2.78 Which compound, M or N, is the stronger acid?...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Explain with the help of resonance structures which of the two nitrogen atoms is more basic in the following molecule.arrow_forwardLabel the most acidic hydrogen in each molecule and justify your choice by using appropriate pKa valuesarrow_forwardQ.4 Identify the structures of A and B from the following reaction. Provide a suitable justification or the formation of these products/- NNHTS NNHTS NABD, NaBH, A B CH;CO,H CH,CO,D indarrow_forward
- (30) Take a look at the two multi-substituted benzene compounds below. Trinitrotoluene (TNT) has its NO, groups on carbons 2, 4, and 6. Which of the two fits this numerical scheme? Hint: Toluene is a special name for benzene whose primary functional group is a methyl group substituted in place of one of its hydrogens. CH3 CH3 O,N. ZON O,N NO2 NO2 NO2arrow_forward(A) what is the hybridization of the nitrogen in each of the following compounds? (B) how does hybridization affect the availability of the lone pair and the basicity of each compound?arrow_forward5.) Which of the analine "units" in the Structure below would have the lowest pka which would have the highest A B H₂N. H₂N. O IZ NH₂ — с NH, D andarrow_forward
- See image belowarrow_forwardAromatic compounds also known as arenes or aromatic are chemical compounds that contain conjugated planar ring system with delocalized pi electron clouds instead of discrete alternating single and double bond. One of the precursor to produce aromatic compounds is arenediazonium.Critize this statementarrow_forwardAnswer Q43, 44, 45arrow_forward
- Please provide degree of unsaturation for the following;arrow_forwardAromatic compounds also known as arenes or aromatics are chemical compounds that contain conjugated planar ring systems with delocalized pi electron clouds instead of discrete alternating single and double bonds. One of the precursor to produce aromatic compounds is arenediazonium salt. Criticize this statement. 4.arrow_forwarda) Account for the pKa trend observed in these compounds. NH2 ÓCH3 THN" H2N CN CN pKa 8.54 7.80 5.34arrow_forward
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