Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
9th Edition
ISBN: 9781305922198
Author: John E. McMurry
Publisher: CENGAGE L
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18.2, Problem 2P
Why do you suppose only symmetrical ethers are prepared by the sulfuric-acid-catalyzed dehydration procedure? What product(s) would you expect if ethanol and 1-propanol were allowed to react together? In what ratio would the products be formed if the two alcohols were of equal reactivity?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
LTS
Solid:
AT=Te-Ti
Trial 1
Trial 2
Trial 3
Average
ΔΗ
Mass water, g
24.096
23.976
23.975
Moles of solid, mol
0.01763
001767
0101781
Temp. change, °C
2.9°C
11700
2.0°C
Heat of reaction, J
-292.37J -170.473
-193.26J
AH, kJ/mole
16.58K 9.647 kJ 10.85 kr
16.58K59.64701
KJ
mol
12.35k
Minimum AS,
J/mol K
41.582
mol-k
Remember: q = mCsAT (m = mass of water, Cs=4.184J/g°C) & qsin =-qrxn &
Show your calculations for:
AH in J and then in kJ/mole for Trial 1:
qa (24.0969)(4.1845/g) (-2.9°C)=-292.37J
qsin =
qrxn =
292.35 292.37J
AH in J = 292.375 0.2923kJ
0.01763m01
=1.65×107
AH in kJ/mol =
=
16.58K
0.01763mol
mol
qrx
Minimum AS in J/mol K (Hint: use the average initial temperature of the three trials, con
Kelvin.)
AS=AHIT
(1.65×10(9.64×103) + (1.0
Jimai
For the compound: C8H17NO2
Use the following information to come up with a plausible structure:
8
This compound has "carboxylic acid amide" and ether functional groups.
The peaks at 1.2ppm are two signals that are overlapping one another.
One of the two signals is a doublet that represents 6 hydrogens; the
other signal is a quartet that represents 3 hydrogens.
Vnk the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest bolling
point, choose 2 next to the substance with the next highest boiling point, and so on.
substance
C
D
chemical symbol,
chemical formula
or Lewis structure.
CH,-N-CH,
CH,
H
H 10: H
C-C-H
H H H
Cale
H 10:
H-C-C-N-CH,
Bri
CH,
boiling point
(C)
Сен
(C) B
(Choose
Chapter 18 Solutions
Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6PCh. 18.3 - Prob. 7PCh. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...
Ch. 18.5 - Prob. 11PCh. 18.6 - Predict the major product of each of the following...Ch. 18.6 - Prob. 13PCh. 18.6 - Predict the major product of the following...Ch. 18.7 - 15-Crown-5 and 12-crown-4 ethers complex Na+ and...Ch. 18.8 - Prob. 16PCh. 18.8 - 2-Butene-l-thiol is one component of skunk spray....Ch. 18.9 - The 1H NMR spectrum shown is that of a cyclic...Ch. 18.SE - Give IUPAC names for the following compounds...Ch. 18.SE - Show the product, including stereochemistry, that...Ch. 18.SE - Prob. 21VCCh. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Prob. 23MPCh. 18.SE - Prob. 24MPCh. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - The alkoxymercuration of alkenes involves the...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Prob. 29MPCh. 18.SE - Ethers undergo an acid-catalyzed cleavage reaction...Ch. 18.SE - Treatment of 1, 1-diphenyl-l, 2-epoxyethane with...Ch. 18.SE - Fluoxetine, a heavily prescribed antidepressant...Ch. 18.SE - When 2-methyl-2, 5-pentanediol is treated with...Ch. 18.SE - Prob. 34MPCh. 18.SE - Prob. 35MPCh. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Prob. 38APCh. 18.SE - Prob. 39APCh. 18.SE - How would you prepare the following ethers?Ch. 18.SE - Prob. 41APCh. 18.SE - tert-Butyl ethers can be prepared by the reaction...Ch. 18.SE - Treatment of trans-2-chlorocyclohexanol with NaOH...Ch. 18.SE - Predict the products of the following ether...Ch. 18.SE - Prob. 45APCh. 18.SE - Prob. 46APCh. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - Prob. 48APCh. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Prob. 50APCh. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Prob. 52APCh. 18.SE - The red fox (Vulpes vulpes) uses a chemical...Ch. 18.SE - Anethole, C10H12O, a major constituent of the oil...Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 56GPCh. 18.SE - How would you synthesize anethole (Problem 18-54)...Ch. 18.SE - How could you prepare benzyl phenyl ether from...Ch. 18.SE - Meerwein's reagent, triethyloxonium...Ch. 18.SE - Prob. 60GPCh. 18.SE - Prob. 61GPCh. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Prob. 63GPCh. 18.SE - Prob. 64GPCh. 18.SE - Prob. 65GPCh. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 68GPCh. 18.SE - Prob. 69GPCh. 18.SE - Predict the product(s) if the starting materials...
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
- Please help me find the 1/Time, Log [I^-] Log [S2O8^2-], Log(time) on the data table. With calculation steps. And the average for runs 1a-1b. Please help me thanks in advance. Will up vote!arrow_forwardQ1: Answer the questions for the reaction below: ..!! Br OH a) Predict the product(s) of the reaction. b) Is the substrate optically active? Are the product(s) optically active as a mix? c) Draw the curved arrow mechanism for the reaction. d) What happens to the SN1 reaction rate in each of these instances: 1. Change the substrate to Br "CI 2. Change the substrate to 3. Change the solvent from 100% CH3CH2OH to 10% CH3CH2OH + 90% DMF 4. Increase the substrate concentration by 3-fold.arrow_forwardExperiment 27 hates & Mechanisms of Reations Method I visual Clock Reaction A. Concentration effects on reaction Rates Iodine Run [I] mol/L [S₂082] | Time mo/L (SCC) 0.04 54.7 Log 1/ Time Temp Log [ ] 13,20] (time) / [I] 199 20.06 23.0 30.04 0.04 0.04 80.0 22.8 45 40.02 0.04 79.0 21.6 50.08 0.03 51.0 22.4 60-080-02 95.0 23.4 7 0.08 0-01 1970 23.4 8 0.08 0.04 16.1 22.6arrow_forward
- (15 pts) Consider the molecule B2H6. Generate a molecular orbital diagram but this time using a different approach that draws on your knowledge and ability to put concepts together. First use VSEPR or some other method to make sure you know the ground state structure of the molecule. Next, generate an MO diagram for BH2. Sketch the highest occupied and lowest unoccupied MOs of the BH2 fragment. These are called frontier orbitals. Now use these frontier orbitals as your basis set for producing LGO's for B2H6. Since the BH2 frontier orbitals become the LGOS, you will have to think about what is in the middle of the molecule and treat its basis as well. Do you arrive at the same qualitative MO diagram as is discussed in the book? Sketch the new highest occupied and lowest unoccupied MOs for the molecule (B2H6).arrow_forwardQ8: Propose an efficient synthesis of cyclopentene from cyclopentane.arrow_forwardQ7: Use compound A-D, design two different ways to synthesize E. Which way is preferred? Please explain. CH3I ONa NaOCH 3 A B C D E OCH3arrow_forward
- Predict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forward(10 pts) The density of metallic copper is 8.92 g cm³. The structure of this metal is cubic close-packed. What is the atomic radius of copper in copper metal?arrow_forwardPredict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forward
- Predict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forwardQ3: Rank the following compounds in increasing reactivity of E1 and E2 eliminations, respectively. Br ca. go do A CI CI B C CI Darrow_forwardQ5: Predict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2). H₂O דיי "Br KN3 CH3CH2OH NaNH2 NH3 Page 3 of 6 Chem 0310 Organic Chemistry 1 HW Problem Sets CI Br excess NaOCH 3 CH3OH Br KOC(CH3)3 DuckDuckGarrow_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
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY