Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 15, Problem 15PP
PRACTICE PROBLEM 15.15
Suppose you needed to synthesize m-chloroethylbenzene from benzene.
You could begin by chlorinating benzene and then follow with a Friedel–Crafts alkylation using chloroethane and
(a) Why will neither method give the desired product?
(b) There is a three-step method that will work if the steps are done in the right order. What is this method?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Alcohols can be synthesized using an acid-catalyzed hydration of an alkene. An alkene is combined with aqueous acid (e.. sulfuric acid in water). The
reaction mechanism typically involves a carbocation intermediate.
>
3rd attempt
3343
10
8
Draw arrows to show the reaction between the alkene and hydronium ion.
that
2nd attempt
Feedback
1st attempt
تعمال
Ju See Periodic Table See Hint
F
D
Ju See Periodic Table See Hint
Draw the simplified curved arrow mechanism for the reaction of acetone and CHgLi to give the major product.
4th attempt
Π
Draw the simplified curved arrow mechanism
T
3rd attempt
Feedback
Ju
See Periodic Table See Hint
H
-H
H
-I
H
F
See Periodic Table See Hint
Select the correct reagent to accomplish the first step of this reaction. Then draw a mechanism on the Grignard reagent using curved arrow notation
to show how it is converted to the final product.
4th attempt
Part 1 (0.5 point)
Select the correct reagent to accomplish the first step of this reaction.
Choose one:
OA Mg in ethanol (EtOH)
OB. 2 Li in THF
O C. Li in THF
D. Mg in THF
O E Mg in H2O
Part 2 (0.5 point)
Br
Part 1
Bri
Mg
CH
B
CH,
1 Draw intermediate here, but no arrows.
©
TE
See Periodic Table See Hint
See Hint
ין
H
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - PRACTICE PROBLEM 15.1
Show how loss of a proton...Ch. 15 - Prob. 2PPCh. 15 - PRACTICE PROBLEM 15.3
Outline all steps in a...Ch. 15 - PRACTICE PROBLEM 15.4 Provide a mechanism that...Ch. 15 - Prob. 5PPCh. 15 - PRACTICE PROBLEM
15.6 Explain how the percentages...Ch. 15 - PRACTICE PROBLEM
15.7
Predict the major products...Ch. 15 - Prob. 8PPCh. 15 - Prob. 9PPCh. 15 - Prob. 10PP
Ch. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.13
Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15
Suppose you needed to...Ch. 15 - PRACTICE PROBLEM
15.16 Predict the major product...Ch. 15 - PRACTICE PROBLEM Account for the following...Ch. 15 - PRACTICE PROBLEM 1-Chloro-3-methyl-2-butene...Ch. 15 - Prob. 19PPCh. 15 - PRACTICE PROBLEM
15.20 The following chlorides (Ph...Ch. 15 - Prob. 21PPCh. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 24PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Predict the major product (or products) formed...Ch. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Predict the major products of the following...Ch. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Starting with aniline, outline a synthesis of each...Ch. 15 - Prob. 36PCh. 15 - 15.37 Propose structures for compounds G–I:
Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Show how you might synthesize each of the...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Treating cyclohexene with acetyl chloride and...Ch. 15 - 15.47 The tert-butyl group can be used as a...Ch. 15 - When toluene is sulfonated (concentrated H2SO4) at...Ch. 15 - Prob. 49PCh. 15 - 15.50 Heating 1,1,1-triphenylmethanol with ethanol...Ch. 15 - 15.51
(a) Which of the following halides would you...Ch. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 54PCh. 15 - When compound C, which is often used to model a...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...Ch. 15 - Which of the following compounds would be most...Ch. 15 - 15.2 Which of the following is not a...Ch. 15 - Prob. 3QCh. 15 - Complete the following syntheses.
Additional Science Textbook Solutions
Find more solutions based on key concepts
A radiant heat lamp is a rod, tong and in diameter through which of electric energy is deposited Assume that th...
Fundamentals Of Thermodynamics
Why can algae and cyanobacteria be considered indicators of productivity as well as of pollution?
Laboratory Experiments in Microbiology (12th Edition) (What's New in Microbiology)
1.1 Write a one-sentence definition for each of the following:
a. chemistry
b. chemical
Chemistry: An Introduction to General, Organic, and Biological Chemistry (13th Edition)
a. Draw the mechanism for the following reaction if it a involves specific-base catalysis. b. Draw the mechanis...
Organic Chemistry (8th Edition)
MAKE CONNECTIONS The gene that causes sickle-cell disease is present in a higher percentage of residents of su...
Campbell Biology (11th Edition)
33. Write an equilibrium expression for each chemical equation for each chemical equation involving one or more...
Chemistry: Structure and Properties (2nd Edition)
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
- Select the product for the following reaction. HO HO PCC OH ○ OH O HO ○ HO HO HOarrow_forward5:45 Х Select the final product for the following reaction sequence. O O 1. Mg. ether 2.D.Oarrow_forwardBased on the chart Two similarities between the molecule with alpha glycosidic linkages. Two similarities between the molecules with beta glycosidtic linkages. Two differences between the alpha and beta glycosidic linkages.arrow_forward
- please help fill in the tablearrow_forwardAnswer F pleasearrow_forward4. Refer to the data below to answer the following questions: The octapeptide saralasin is a specific antagonist of angiotensin II. A derivative of saralasin is used therapeutically as an antihypertensive. Amino acid analysis of saralasin show the presence of the following amino acids: Ala, Arg, His, Pro, Sar, Tyr, Val, Val A.Sar is the abbreviation for sarcosine, N-methyl aminoethanoic acid. Draw the structure of sarcosine. B. N-Terminal analysis by the Edman method shows saralasin contains sarcosine at the N-terminus. Partial hydrolysis of saralasin with dilute hydrochloric acid yields the following fragments: Tyr-Val-His Sar-Arg-Val His-Pro-Ala Val-Tyr-Val Arg-Val-Tyr What is the structure of saralasin?arrow_forward
- What is the structure of the DNA backbone?arrow_forwardPLEASE PLEASE PLEASE use hand drawn structures when possarrow_forward. M 1- MATCH each of the following terms to a structure from the list below. There is only one correct structure for each term and structures may be used more than once. Place the letter of the structure in the blank to the left of the corresponding term. A. Sanger dideoxy method C. Watson-Crick B. GAUCGUAAA D. translation E. HOH2C OH OH G. transcription I. AUGGCUGAG 0 K. OPOH2C 0- OH N- H NH2 F. -OPOH2C 0- OH OH H. Maxam-Gilbert method J. replication N L. HOH2C a. b. C. d. e. f. g. B M. AGATCGCTC a pyrimidine nucleoside RNA base sequence with guanine at the 3' end. DNA base sequence with cytosine at the 3' end. a purine nucleoside DNA sequencing method for the human genome 2'-deoxyadenosine 5'-phosphate process by which mRNA directs protein synthesis OH NH2arrow_forward
- Please use hand drawn structures when neededarrow_forwardB. Classify the following amino acid. Atoms other than carbon and hydrogen are labeled. a. acidic b. basic C. neutral C. Consider the following image. Which level of protein structure is shown here? a. primary b. secondary c. tertiary d. quaternary D. Consider the following image. H RH H HR H R HR HR RH Which level of protein structure is shown in the box? a. primary b. secondary R c. tertiary d. quaternary コー Rarrow_forwardBriefly answer three from the followings: a. What are the four structures of the protein? b. Why is the side chain (R) attached to the alpha carbon in the amino acids is important for the function? c. What are the types of amino acids? And how is it depend on the (R) structure? d. Write a reaction to prepare an amino acid. prodarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY