ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN
4th Edition
ISBN: 9781119760924
Author: Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 13, Problem 49ASP
Interpretation Introduction
Interpretation: The disconnection that leads to an
Concept Introduction: The ring opening in epoxide is basically a reaction between nucleophile and an electrophile. In this case, oxygen atom resulting in epoxide ring act as an electrophile and other group act as a nucleophile.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
20:32
hydroxide
2. Using curved arrows, show the deprotonation mechanism of phenol with
(OH). Also, provide the structure of the product of this deprotonation.
Start answering this question by drawing the structure of phenol. Then
hydroxide ion. Find your most reactive electrons and draw the curved arrow that
shows where they would go to deprotonate phenol. Then "make a bond break a
bond"
write they
question
3. Provide valid resonance structures for the product of
the previous
arrow(s)
charge moving onto the ortho- and para positions. Use curved
to show how the charge resonates to the next structure in your scheme.
all the proper notations for depicting resonance.
that show the
in the structures
Be sure to use
Send a chat
C
Thiols or thiol (-SH) group is a better base than hydroxide (-OH) group in elimination reactions.
The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles.
Identify the product that is formed when the conjugate base of diethyl malonate reacts with the following
electrophile followed by acid workup when relevant:
Modify the provided structures of diethyl malonate and the given electrophile to draw the product formed.
Note: the eraser tool can be used to erase bonds, and atoms can be moved by selecting them with the selector
tool and then dragging the selected atom(s) to a new position. If you make a mistake, you can use Ctrl-Z or the
Undo tool.
бль
EtO
OEt
Edit Drawing
Chapter 13 Solutions
ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN
Ch. 13.2 - Prob. 1LTSCh. 13.2 - Prob. 1PTSCh. 13.2 - Prob. 2PTSCh. 13.2 - Prob. 3ATSCh. 13.4 - Prob. 4CCCh. 13.5 - Prob. 2LTSCh. 13.5 - Prob. 5PTSCh. 13.5 - Prob. 6ATSCh. 13.5 - Prob. 7CCCh. 13.5 - Prob. 8CC
Ch. 13.5 - Prob. 9CCCh. 13.6 - Prob. 10CCCh. 13.7 - Prob. 11CCCh. 13.7 - Prob. 12CCCh. 13.8 - Prob. 3LTSCh. 13.8 - Prob. 13PTSCh. 13.8 - Prob. 14ATSCh. 13.9 - Prob. 15CCCh. 13.10 - Prob. 4LTSCh. 13.10 - Prob. 17ATSCh. 13.10 - Prob. 5LTSCh. 13.10 - Prob. 19ATSCh. 13.11 - Prob. 20CCCh. 13.12 - Prob. 6LTSCh. 13.12 - Prob. 7LTSCh. 13 - Prob. 26PPCh. 13 - Prob. 27PPCh. 13 - Prob. 28PPCh. 13 - Prob. 29PPCh. 13 - Prob. 30PPCh. 13 - Prob. 31PPCh. 13 - Prob. 32PPCh. 13 - Prob. 33PPCh. 13 - Prob. 34PPCh. 13 - Prob. 35PPCh. 13 - Prob. 36PPCh. 13 - Prob. 37PPCh. 13 - Prob. 38PPCh. 13 - Prob. 39PPCh. 13 - Prob. 40PPCh. 13 - Prob. 41PPCh. 13 - Prob. 42PPCh. 13 - Prob. 43PPCh. 13 - Prob. 44PPCh. 13 - Prob. 45PPCh. 13 - Prob. 46ASPCh. 13 - Prob. 47ASPCh. 13 - Prob. 48ASPCh. 13 - Prob. 49ASPCh. 13 - Prob. 50ASPCh. 13 - Prob. 51ASPCh. 13 - Prob. 52ASPCh. 13 - Prob. 53ASPCh. 13 - Prob. 54IPCh. 13 - Prob. 59IPCh. 13 - Prob. 60IPCh. 13 - Prob. 61IPCh. 13 - Prob. 62IPCh. 13 - Prob. 63IPCh. 13 - Prob. 64IPCh. 13 - Prob. 65IPCh. 13 - Prob. 66IPCh. 13 - Prob. 69IPCh. 13 - Prob. 70IPCh. 13 - Prob. 71IPCh. 13 - Prob. 72IPCh. 13 - Prob. 73IPCh. 13 - Prob. 74IPCh. 13 - Prob. 77CPCh. 13 - Prob. 79CPCh. 13 - Prob. 80CP
Knowledge Booster
Similar questions
- The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is formed when the conjugate base of diethyl malonate reacts with the following electrophile followed by acid workup when relevant: Modify the provided structures of diethyl malonate and the given electrophile to draw the product formed. Note: the eraser tool can be used to erase bonds, and atoms can be moved by selecting them with the selector tool and then dragging the selected atom(s) to a new position. If you make a mistake, you can use Ctrl-Z or the Undo tool. OH -CH₂ CH₂ Edit Drawingarrow_forwardHydroxide acts as a nucleophile in protein degradation by hydrolysis of the peptide bond in water. Draw out an arrow pushing mechanism of the hydrolysis of a peptide bond. Identify the nucleophile and the electrophile in this reaction.arrow_forwardthis drug contains one or more building blocks derived from either ethylene oxide or epichlorohydrin.Identify the part of each molecule that can be derived from one or the other of the building block and propose structural formulas for the nucleophile(s) that can be used along with either ethylene oxide or epichlorohydrin to synthesize each molecule.arrow_forward
- Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.arrow_forwardDirections: Check which tests does the unknown compounds got positive results. Test Positive result A B C D E Chromic blue-green to opaque- green solution acid Test Tollen's test Silver mirror coat Lucas Test Turbid fast Iodoform Pale Yellow ppt Testarrow_forwardBecause phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.arrow_forward
- 3. You are given a mixture of aspirin, phenol, and naphthalene that you need to separate. i) Draw the structures of each, and identify if they are acidic, basic, or neutral compounds. For each compound draw their reaction with the appropriate acidic or basic conditions that will change their solubility and allow them to be separated. ii) What modifications would you have to make to the experimental protocol in order to separate these three compounds? Provide specifics.arrow_forwardQUESTION 5 Following a reaction period of 150-minutes, you decide to perform an extraction to eliminate any triethylammonium chloride salts that formed as well as any potential remaining starting materials. You transfer the reaction mixture to a separatory funnel and add distilled water. Identify the layers in the separatory funnel. The top layer is the aqueous layer, and the bottom layer is the organic layer. The top layer is the organic layer, and the bottom layer is the aqueous layer. DCM and water are miscible solvents, and no layers form. Performing an extraction was a mistake. A distillation should have been used to purify the desired material. O Oarrow_forwardThe conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is formed when the conjugate base of diethyl malonate reacts with the following electrophile followed by acid workup when relevant: CN Modify the provided structures of diethyl malonate and the given electrophile to draw the product formed. Note: the eraser tool can be used to erase bonds, and atoms can be moved by selecting them with the selector tool and then dragging the selected atom(s) to a new position. If you make a mistake, you can use Ctrl-Z or the Undo tool. EtO H3C CN Edit Drawing OEtarrow_forward
- Why is methyl salicylate so easily absorbed through the skin?arrow_forwardThe reaction between propanoic acid and benzyl alcohol in an acidic medium. Show the product by writing the reaction together with its mechanism.arrow_forwardFrom the table of reagents, select the reagents and conditions necessary to carry out the following reaction.arrow_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 LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher: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
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning