EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 21.SE, Problem 36MP
When 4-dimethylaminopyridine (DMAP) is added in catalytic amounts to acetic anhydride and an alcohol, it significantly increases the rate of ester formation. The process begins with a reaction between acetic anhydride and DMAP to form a highly reactive acetylpyridinium intermediate that is more reactive than acetic anhydride itself. Propose a mechanism for this process that includes the formation and reaction of the acetylpyridinium intermediate.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
0+
aleksog/x/lsl.exe/1ou-lgNgkr7j8P3H-IQs pBaHhviTCeeBZbufuBYTOHz7m7D3ZStEPTBSB3u9bsp3Da pl19qomOXLhvWbH9wmXW5zm
O States of Matter
Sketching a described thermodynamic change on a phase diagram
0/5
Gab
The temperature on a sample of pure X held at 0.75 atm and -229. °C is increased until the sample sublimes. The temperature is then held constant and the
pressure is decreased by 0.50 atm. On the phase diagram below draw a path that shows this set of changes.
F3
pressure (atm)
0-
0
200
Explanation
temperature (K)
Check
F4
F5
☀+
Q Search
Chill Will an
9
ENG
F6
F7
F8
F9
8
Delete
F10
F11
F12
Insert
PrtSc
114
d
Ar
x +
LEKS: Using a phase diagram a X
n/alekscgi/x/lsl.exe/10_u-IgNsikr7j8P3jH-IQs_pBan HhvlTCeeBZbufu BYTI0Hz7m7D3ZcHYUt80XL-5alyVpw
○ States of Matter
Using a phase diagram to find a phase transition temperature or pressure
Use the phase diagram of Substance X below to find the melting point of X when the pressure above the solid is 1.1 atm.
pressure (atm)
16
08-
solid
liquid-
0
200
400
gas
600
temperature (K)
Note: your answer must be within 25 °C of the exact answer to be graded correct.
×
5
S: Using a phase diagram
leksogi/x/sl.exe/1ou-IgNs kr 7j8P3jH-IQs_pBan HhvTCeeBZbufuBYTI0Hz7m7D3ZdHYU+80XL-5alyVp
O States of Matter
Using a phase diagram to find a phase transition temperature or pressure
se the phase diagram of Substance X below to find the boiling point of X when the pressure on the liquid is 1.6 atm.
pressure (atm)
32-
16-
solid
liquid
0.
gas
100
200
temperature (K)
300
Note: your answer must be within 12.5 °C of the exact answer to be graded correct.
10
Explanation
Check
§
Q Search
J
2025 McGraw Hill LLC. All Rights Rese
Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
Ch. 21.1 - Give IUPAC names for the following substances:Ch. 21.1 - Draw structures corresponding to the following...Ch. 21.2 - Prob. 3PCh. 21.2 - Rank the compounds in each of the following sets...Ch. 21.2 - Predict the products of the following nucleophilic...Ch. 21.2 - Prob. 6PCh. 21.3 - Prob. 7PCh. 21.3 - If the following molecule is treated with acid...Ch. 21.4 - How might you prepare the following esters using a...Ch. 21.4 - Prob. 10P
Ch. 21.4 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - What product would you expect from reaction of one...Ch. 21.6 - Prob. 16PCh. 21.6 - Prob. 17PCh. 21.6 - Show the products you would obtain by reduction of...Ch. 21.6 - What ester and what Grignard reagent might you...Ch. 21.7 - Prob. 20PCh. 21.7 - How would you use the reaction of an amide with...Ch. 21.8 - Write the mechanism of the reaction shown in...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.10 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.SE - Name the following compounds:Ch. 21.SE - Prob. 28VCCh. 21.SE - Prob. 29VCCh. 21.SE - Prob. 30VCCh. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the mechanism...Ch. 21.SE - Predict the product(s) and provide the complete...Ch. 21.SE - Prob. 35MPCh. 21.SE - When 4-dimethylaminopyridine (DMAP) is added in...Ch. 21.SE - Prob. 37MPCh. 21.SE - Prob. 38MPCh. 21.SE - Prob. 39MPCh. 21.SE - The hydrolysis of a biological thioester to the...Ch. 21.SE - Prob. 41MPCh. 21.SE - Prob. 42MPCh. 21.SE - Prob. 43MPCh. 21.SE - In the iodoform reaction, a triiodomethyl ketone...Ch. 21.SE - Give IUPAC names for the following compounds:Ch. 21.SE - Prob. 46APCh. 21.SE - Draw and name compounds that meet the following...Ch. 21.SE - Predict the product, if any, of reaction between...Ch. 21.SE - Prob. 49APCh. 21.SE - Prob. 50APCh. 21.SE - What product would you expect to obtain from...Ch. 21.SE - Prob. 52APCh. 21.SE - Prob. 53APCh. 21.SE - The following reactivity order has been found for...Ch. 21.SE - Prob. 55APCh. 21.SE - Outline methods for the preparation of...Ch. 21.SE - Prob. 57APCh. 21.SE - When ethyl benzoate is heated in methanol...Ch. 21.SE - tert-Butoxycarbonyl azide, a reagent used in...Ch. 21.SE - Prob. 60APCh. 21.SE - Prob. 61APCh. 21.SE - What is the structure of the polymer produced by...Ch. 21.SE - Polyimides with the structure shown are used as...Ch. 21.SE - Prob. 64APCh. 21.SE - Propose a structure for a compound, C4H7ClO2, that...Ch. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Prob. 67APCh. 21.SE - When a carboxylic acid is dissolved in...Ch. 21.SE - Prob. 69APCh. 21.SE - Prob. 70APCh. 21.SE - Prob. 71APCh. 21.SE - Phenyl 4-aminosalicylate is a drug used in the...Ch. 21.SE - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 21.SE - Tranexamic acid, a drug useful against blood...Ch. 21.SE - One frequently used method for preparing methyl...Ch. 21.SE - Prob. 76APCh. 21.SE - Assign structures to compounds with the following...Ch. 21.SE - Propose structures for compounds with the...Ch. 21.SE - Propose a structure for the compound with the...Ch. 21.SE - Draw the structure of the compound that produced...Ch. 21.SE - Prob. 81APCh. 21.SE - Epoxy adhesives are prepared in two steps. SN2...
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
- 151.2 254.8 85.9 199.6 241.4 87.6 242.5 186.4 155.8 257.1 242.9 253.3 256.0 216.6 108.7 239.0 149.7 236.4 152.1 222.7 148.7 278.2 268.7 234.4 262.7 283.2 143.6 QUESTION: Using this group of data on salt reduced tomato sauce concentration readings answer the following questions: 1. 95% Cl Confidence Interval (mmol/L) 2. [Na+] (mg/100 mL) 3. 95% Na+ Confidence Interval (mg/100 mL)arrow_forwardResults Search Results Best Free Coursehero Unloc xb Success Confirmation of Q x O Google Pas alekscgi/x/lsl.exe/1o_u-IgNslkr 7j8P3jH-IQs_pBanHhvlTCeeBZbufu BYTI0Hz7m7D3ZcHYUt80XL-5alyVpwDXM TEZayFYCavJ17dZtpxbFD0Qggd1J O States of Matter Using a phase diagram to find a phase transition temperature or pressure Gabr 3/5 he pressure above a pure sample of solid Substance X at 101. °C is lowered. At what pressure will the sample sublime? Use the phase diagram of X below to nd your answer. pressure (atm) 24- 12 solid liquid gas 200 400 temperature (K) 600 ote: your answer must be within 0.15 atm of the exact answer to be graded correct. atm Thanation Check © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center I Q Search L³ ملةarrow_forward301.7 348.9 193.7 308.6 339.5 160.6 337.7 464.7 223.5 370.5 326.6 327.5 336.1 317.9 203.8 329.8 221.9 331.7 211.7 309.6 223.4 353.7 334.6 305.6 340.0 304.3 244.7 QUESTION: Using this group of data on regular tomato sauce concentration readings answer the following questions: 1. 95% Cl Confidence Interval (mmol/L) 2. [Na+] (mg/100 mL) 3. 95% Na+ Confidence Interval (mg/100 mL)arrow_forward
- Search Results Search Results Best Free Coursehero Unlo x b Success Confirmation of Q aleks.com/alekscgi/x/sl.exe/10_u-lgNslkr7j8P3jH-IQs_pBan HhvlTCeeBZbufu BYTIOHz7m7D3ZcHYUt80XL-5alyVpwDXM TEZayFYCav States of Matter Using a phase diagram to find a phase transition temperature or pressure Use the phase diagram of Substance X below to find the temperature at which X turns to a gas, if the pressure above the solid is 3.7 atm. pressure (atm) 0. 32- 16 solid liquid gas 200 temperature (K) Note: your answer must be within 20 °C of the exact answer to be graded correct. Дос Xarrow_forwardConsider the reaction below to answer the following questions: Acetoacetic ester can be prepared by the Claisen self-condensation reaction of ethyl acetate. 1. NaOEt, EtOH H&C OCH CH3 2 H30 H3C CH2 OCH2CH3 A. Write the complete stepwise mechanism for this reaction. Show all electron flow with arrows and draw all intermediate structures. B. Ethyl acetate can be prepared from ethanol as the only organic starting material. Show all reagents and structures for all intermediates in this preparation. C. Give the structures of the ester precursors for the following Claisen condensation product and formulate the reaction. OEtarrow_forwardUse the phase diagram of Substance X below to find the temperature at which X turns to a gas, if the pressure above the solid is 3.7 atm. pressure (atm) 32 16 solid liquid gas 0 0 200 temperature (K) Note: your answer must be within 20 °C of the exact answer to be graded correct. Шос ☑ كarrow_forward
- Starting from bromoethane, how could you prepare the following compounds: a. Ethanol. b. Acetaldehyde f. Acetone. e. 2-Propanol i. Acetoacetic ester. d. 2-Bromoacetic acid. c. Acetic acid g. Acetamide. j. Ethylmalonate k. Gama ketoacid. h. Ethyl magnesium bromide.arrow_forward- The pressure above a pure sample of solid Substance X at 60. °C is raised. At what pressure will the sample melt? Use the phase diagram of X below to find your answer. pressure (atm) 02 0.4 solid Hliquid gas 0 0 200 400 600 temperature (K) Note: your answer must be within 0.025 atm of the exact answer to be graded correct. ☐ atmarrow_forward15. What is the order of decreasing reactivity towards nucleophilic acyl substitution for the carboxylic acid derivatives? (most reactive first) 0 O H3C COC CH3 H₂C C N(CH3)2 H3C C OCH3 A. a. I, 11, 111, b. I, III, IV, II C. II, IV, III, I ° (CH3)2CH C OCH3 IV d. II, I, III, IV B. R COCR 0 0 0 13= RC NH2 RC OR RC CI === IV a. I, III, II, IV b. II, III, I, IV C. III, II, I, IV d. IV, I, III, IIarrow_forward
- Draw the formula of the product obtained by reacting D-Tallose with bromine water.arrow_forwardChoose the best reagent(s) for carrying out the following conversions from the list below. Place the letter corresponding to the best choice in the blank to the left of the conversion. a. KMnO4, H3O+ b. Tollens' Reagent [oxidizing reagent] C. NaBH4, ethanol d. 1. BH3 2. H3O+ e. 1. CH3MgBr, ether 2. H3O+ f. CrO3, H2SO4, H₂O g. 1. Mg, ether 2. CO2 3. H3O+ h. 1. NaCN 2. H2SO4, H2, heat i. O3, then Zn and HOAC j. CH₂I A. B. C. CH CH=CHCH2COOH Br CEN CH COOH + HOOCCH COOH COOH 010 CH3arrow_forwardDraw the structures for each of the intermediates in the boxes provided for the synthesis below. OCH3 Fe HO HNO (CHOO pynding H₂504 LHNO2 NACH-I Fa H₂O HCL HNO 180arrow_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
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
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