Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 15, Problem 15.44P
Interpretation Introduction
(a)
Interpretation:
Problem 15.43 calls attention to a resonance structure of an amide that accounts for the lowering of the
Concept introduction:
An ester has O atom having a lone pair on it. The lone pair on O atom participates in resonance with
Interpretation Introduction
(b)
Interpretation:
Problem 15.43 calls attention to a resonance structure of an amide that accounts for the lowering of the
Concept introduction:
The
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The chemical shifts of the a protons on cyclohexanone
and cyclobutanone are as shown here: (a) Which a
carbon has a greater effective electronegativity? (b) Can
you explain why, using arguments of s character and p
2.4 ppm
3.0 ppm
character?
Cyclohexanone
Cyclobutanone
The following molecules and ions are grouped by similar structures. Classify each as aromatic, antiaromatic, or
nonaromatic. For the aromatic and antiaromatic species, give the number of pi electrons in the ring.
(а) нн
H
H
(b)
H
H
H
H
H
H
H
H
(c)
(d)
H
H
+,
+
H
H
(e)
(f)
H,
H.
H
(h)
CH,
H
H
H.
B.
Compounds P and Q can undergo a Diels-Alder reaction to form two
regioisomeric products R and S as shown in Figure 5.
OMe
P
H
C8H1202
R
C8H1202
S
Figure 5
Draw the chemical structures of regioisomeric compounds R and S.
(ii) Using possible resonance contributors of P and Q predict which of the two
regioisomers will be favoured in the reaction.
(iii) Using curly arrows, draw the mechanism for the reaction of P and Q to form the
dominant regioisomer you have predicted in your answer to part (ii) above.
Chapter 15 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42PCh. 15 - Prob. 15.43PCh. 15 - Prob. 15.44PCh. 15 - Prob. 15.45PCh. 15 - Prob. 15.46PCh. 15 - Prob. 15.47PCh. 15 - Prob. 15.48PCh. 15 - Prob. 15.49PCh. 15 - Prob. 15.50PCh. 15 - Prob. 15.51PCh. 15 - Prob. 15.52PCh. 15 - Prob. 15.53PCh. 15 - Prob. 15.54PCh. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - Prob. 15.57PCh. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - Prob. 15.60PCh. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - Prob. 15.63PCh. 15 - Prob. 15.64PCh. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - Prob. 15.67PCh. 15 - Prob. 15.68PCh. 15 - Prob. 15.1YTCh. 15 - Prob. 15.2YTCh. 15 - Prob. 15.3YTCh. 15 - Prob. 15.4YTCh. 15 - Prob. 15.5YTCh. 15 - Prob. 15.6YTCh. 15 - Prob. 15.7YTCh. 15 - Prob. 15.8YTCh. 15 - Prob. 15.9YTCh. 15 - Prob. 15.10YTCh. 15 - Prob. 15.11YTCh. 15 - Prob. 15.12YTCh. 15 - Prob. 15.13YTCh. 15 - Prob. 15.14YTCh. 15 - Prob. 15.15YTCh. 15 - Prob. 15.16YTCh. 15 - Prob. 15.17YTCh. 15 - Prob. 15.18YTCh. 15 - Prob. 15.19YTCh. 15 - Prob. 15.20YTCh. 15 - Prob. 15.21YTCh. 15 - Prob. 15.22YTCh. 15 - Prob. 15.23YTCh. 15 - Prob. 15.24YTCh. 15 - Prob. 15.25YTCh. 15 - Prob. 15.26YTCh. 15 - Prob. 15.27YTCh. 15 - Prob. 15.28YTCh. 15 - Prob. 15.29YTCh. 15 - Prob. 15.30YT
Knowledge Booster
Learn more about
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
- Consider the structure of benzaldehyde and its three resonance structures. Add curved arrows to the resonance structures for benzaldehyde to illustrate the electron-withdrawing group's effect on the aromatic ring. The four resonance structures are shown. :0: :ö: :0: Resonance structure A Resonance structure B Resonance structure C Resonance structure Darrow_forwardWhen the 1î-NMR spectrum of acetone, CH3COCH3, is recorded on an instrument operating at 200 MHz, a single sharp resonance at 2.1î is seen. (a) How many hertz downfield from TMS does the acetone resonance correspond to? (b) If the 1î-NMR spectrum of acetone were recorded at 500 MHz, what would the position of the absorption be in î units? (c) How many hertz downfield from TMS does this 500 MHz resonance correspond to?arrow_forward15.10 Analyzing a 'H NMR Spectrum A compound has the molecular formula of C3HgO. It exhibits 4 peaks in its ¹H NMR spectrum. These peaks are (in 6): 3.6 (2H, t). 2.3 (1H, broad), 1.6 (2H, sextet). 1.05 (3H, t). Which of the following compounds is consistent with this data? O CO O O O OMe -OH OH H₂C-O-CH, OH Save for Later C Submit Answerarrow_forward
- Which is a resonance contributor for this molecule? :ö:arrow_forwardA compound with a resonance that increases the stability of its conjugate acid is a strong acid. (A) True (B) Falsearrow_forward6）Rank the following compounds in order of increasing pKa values, and explain your choices in detail.arrow_forward
- Rank the molecules in decreasing (strongest to weakest) acidity. Include ALL resonance structures with arrows and explain reasoning for rank.arrow_forwardral compounds synthesized by flowers of the genus Chrysanthemum 15.81 Pyrethrins, such as jasmolin II (below), are a group of ne (known as pyrethrum flowers) to act as insecticides. (a) Circle and name the functional groups in jasmolin II. (b) What is the hybridization of the numbered carbons? (c) Which, if any, of the numbered carbons are chiral centers? CH3 CH2=CH-CH, 3. 4 CH-C-O-HC5 C-C-O-CH3 CH3-C H,C-C CH3arrow_forwardIn Section 15.5c, we learned that the frequency of a C=0 stretch decreases when the c=0 bond is conjugated to a C=C bond. Draw the pertinent resonance contributor of a conjugated carbonyl (C=C-c=0) and, based on the resulting resonance hybrid, explain why the frequency decreases.arrow_forward
- The two isomeric carboxylic acids that give the following NMR spectra both have the formula C3H5ClO2. What is the name of the two carboxylic acids.arrow_forwardAzulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon (μ = 1.0 D). Explain, using resonance structures.arrow_forwardAccording to the conventions above, what is the sign ( + or ) of the P.E. change (H) for Rxn 3?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning