Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 22.4, Problem 6P
If methanol rather than water is added at the end of a Hell–Volhard–Zelinskii reaction, an ester rather than an acid is produced. Show how you would carry out the following transformation, and propose a mechanism for the ester forming step.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
>
each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that:
1. the rate of substitution doesn't depend on nucleophile concentration and
2. the products are a roughly 50/50 mixture of enantiomers.
Substrate A
Substrate B
Faster Rate
X
Ś
CI
(Choose one)
(Choose one)
CI
Br
Explanation
Check
Br
(Choose one)
© 2025 McGraw Hill LLC. All Rights F
NMR spectrum of ethyl acetate has signals whose chemical shifts are indicated below. Which hydrogen or set of hydrogens corresponds to the signal at
4.1 ppm? Select the single best answer.
The
H
O
HỌC—C—0—CH, CH,
2
A
ethyl acetate
H NMR: 1.3 ppm, 2.0 ppm, 4.1 ppm
Check
OA
B
OC
ch
B
C
Save For Later
Submit Ass
© 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center |
How many signals do you expect in the H NMR spectrum for this molecule?
Br Br
Write the answer below.
Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H
atoms that would contribute to the same signal as the H already highlighted red
Note for advanced students: In this question, any multiplet is counted as one signal.
1
Number of signals in the 'H NMR spectrum.
For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to
the same signal as the H atom already highlighted red.
If no other H atoms will contribute, check the box at right.
Check
For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute
to the same signal as the H atom already highlighted red.
If no other H atoms will contribute, check the box at right.
O
✓
No additional Hs to color in top
molecule
ง
No additional Hs to color in bottom…
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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
- in the kinetics experiment, what were the values calculated? Select all that apply.a) equilibrium constantb) pHc) order of reactiond) rate contstantarrow_forwardtrue or false, given that a 20.00 mL sample of NaOH took 24.15 mL of 0.141 M HCI to reach the endpoint in a titration, the concentration of the NaOH is 1.17 M.arrow_forwardin the bromothymol blue experiment, pKa was measured. A closely related compound has a Ka of 2.10 x 10-5. What is the pKa?a) 7.1b) 4.7c) 2.0arrow_forward
- calculate the equilibrium concentration of H2 given that K= 0.017 at a constant temperature for this reaction. The inital concentration of HBr is 0.050 M.2HBr(g) ↔ H2(g) + Br2(g)a) 4.48 x 10-2 M b) 5.17 x 10-3 Mc) 1.03 x 10-2 Md) 1.70 x 10-2 Marrow_forwardtrue or falsegiven these two equilibria with their equilibrium constants:H2(g) + CI2(l) ↔ 2HCI(g) K= 0.006 CI2(l) ↔ CI2(g) K= 0.30The equilibrium contstant for the following reaction is 1.8H2(g) + CI2 ↔ 2HCI(g)arrow_forwardI2(g) + CI2(g) ↔ 2ICIK for this reaction is 81.9. Find the equilibrium concentration of I2 if the inital concentration of I2 and CI2 are 0.010 Marrow_forward
- true or false,the equilibrium constant for this reaction is 0.50.PCI5(g) ↔ PCI3(g) + CI2(g)Based on the above, the equilibrium constant for the following reaction is 0.25.2PCI5(g) ↔. 2PCI3(g) + 2CI2(g)arrow_forwardtrue or false, using the following equilibrium, if carbon dioxide is added the equilibrium will shift toward the productsC(s) + CO2(g) ↔ 2CO(g)arrow_forward2S2O2/3- (aq) + I2 (aq) ---> S4O2/6- (aq) +2I- (aq) Experiment I2 (M) S2O3- (M) Initital Rate (M/s) 1 0.01 0.01 0.0004 2 0.01 0.02 0.0004 3 0.02 0.01 0.0008 Calculate the overall order for this reaction using the table data a) 3b) 0c) 2d) 1arrow_forward
- the decomposition of N2O5 is the first order with a half-life of 1.98 minutes. If the inital concentration of N2O5 is 0.200 M, what is the concentration after 6 minutes?a) 0.612 Mb) 0.035 Mc) 0.024 Md) 0.100 Marrow_forward20.00 mL of 0.150 M HCI is titrated with 0.075 M NaOH. What volume of NaOH is needed?a) 50 mLb) 20 mLc) 40 mLd) 26.66 mLarrow_forward20.00 mL of 0.150 M NaOH is titrated with 37.75 mL of HCI. What is the molarity of the HCI?a) 0.150 Mb) 0.079 Mc) 0.025 Md) 0.050 Marrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License