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
Question
Chapter 6, Problem 12PP
Interpretation Introduction
Interpretation:
The decreasing order of nucleophilicity of the given compound is to be ranked.
Concept introduction:
Nucleophilicity is the phenomena of measuring the ability of any nucleophile to react with an electron deficient species.
Nucleophiles are Lewis bases, mean electron rich and have the ability to donate electron pairs.
The order of nucleophilicity can be decided on the basis of charge.
A negatively charged nucleophile is more reactive than its conjugate acid.
In the given nucleophiles, the negatively charged nucleophiles are more reactive than the neutral one.
The nucleophile attached with electron withdrawing group has less nucleophilicity because electron withdrawing attracts electron density toward itself.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Draw the major products of this SN1 reaction. Ignore any inorganic byproducts.
Draw the major elimination and substitution products formed in this reaction. Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, wehre applicable. Ignore and inorganic byproducts.
Curved arrows are used to illustrate the flow of electrons. Using the provided
starting and product structures, draw the curved electron-pushing arrows for
the following reaction or mechanistic step(s).
Be sure to account for all bond-breaking and bond-making steps.
Drawing Arrows
THE
Problem 33 of 35
N.
C:0
Na +
Submit
Drag To Pan
+
Chapter 6 Solutions
Organic Chemistry
Ch. 6 - Prob. 1PPCh. 6 - Prob. 2PPCh. 6 - Prob. 3PPCh. 6 - Prob. 4PPCh. 6 - Prob. 5PPCh. 6 - PRACTICE PROBLEM 6.6
reactions that involve...Ch. 6 - PRACTICE PROBLEM 6.7 Rank the following...Ch. 6 - Prob. 8PPCh. 6 - Prob. 9PPCh. 6 - Prob. 10PP
Ch. 6 - Prob. 11PPCh. 6 - Prob. 12PPCh. 6 - Prob. 13PPCh. 6 - Prob. 14PPCh. 6 - Prob. 15PPCh. 6 - Prob. 16PPCh. 6 - Prob. 17PPCh. 6 - Prob. 18PPCh. 6 - Prob. 19PPCh. 6 - Prob. 20PCh. 6 - Prob. 21PCh. 6 - Which SN1 reaction of each pair would you expect...Ch. 6 - Prob. 23PCh. 6 - Prob. 24PCh. 6 - Listed below are several hypothetical nucleophilic...Ch. 6 - Prob. 28PCh. 6 - Write conformational structures for the...Ch. 6 - 6.28 Consider the reaction of with .
(a) Would...Ch. 6 - Prob. 33PCh. 6 - Prob. 34PCh. 6 - Prob. 35PCh. 6 - Prob. 36PCh. 6 - 1-Bromobicyclo[2, 2,1] heptane is extremely...Ch. 6 - When ethyl bromide reacts with potassium cyanide...Ch. 6 - Prob. 41PCh. 6 - Prob. 42PCh. 6 - When the alkyl bromides (listed here) were...Ch. 6 - Prob. 44PCh. 6 - Prob. 45PCh. 6 - Prob. 46PCh. 6 - Prob. 47PCh. 6 - 6.42 The reaction of chloroethane with water in...Ch. 6 - Prob. 49PCh. 6 - Prob. 50PCh. 6 - Prob. 51PCh. 6 - Prob. 52PCh. 6 - 1-Bromo[2.2.1] bicycloheptane is unreactive toward...Ch. 6 - Open the computer molecular model tided...Ch. 6 - Prob. 56PCh. 6 - Consider the solvolysis reaction of (1S,...Ch. 6 - 2. Consider the following sequence of reactions,...Ch. 6 - Prob. 26PCh. 6 - Your task is to prepare isopropyl methyl ether by...Ch. 6 - Prob. 29PCh. 6 - 6.53 cis-4-Bromocyclohexanol racemic C6H10O...Ch. 6 - Prob. 31PCh. 6 - Explain the following observations: When...Ch. 6 - Prob. 38PCh. 6 - Prob. 1QCh. 6 - Prob. 2QCh. 6 - 6.3 A kinetic study yielded the following reaction...Ch. 6 - Prob. 4QCh. 6 - 6.5 Supply the missing reactants, reagents,...Ch. 6 - Which SN2 reaction will occur most rapidly....Ch. 6 - 6.7 Provide three-dimensional structures for the...
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
- Draw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore and inorganic byproducts.arrow_forwardDraw the major producrs of this SN1 reaction. Ignore any inorganic byproducts. Use a dash or wedge bond to indicate the sereochemistry of substituents on asymmetric centers where appllicable.arrow_forward5) Oxaloacetic Acid is an important intermediate in the biosynthesis of citric acid. Synthesize oxaloacetic acid using a mixed Claisen Condensation reaction with two different esters and a sodium ethoxide base. Give your answer as a scheme Hint 1: Your final acid product is producing using a decarboxylation reaction. Hint 2: Look up the structure of oxalic acid. HO all OH oxaloacetic acidarrow_forward
- 20. The Brusselator. This hypothetical system was first proposed by a group work- ing in Brussels [see Prigogine and Lefever (1968)] in connection with spatially nonuniform chemical patterns. Because certain steps involve trimolecular reac tions, it is not a model of any real chemical system but rather a prototype that has been studied extensively. The reaction steps are A-X. B+X-Y+D. 2X+ Y-3X, X-E. 305 It is assumed that concentrations of A, B, D, and E are kept artificially con stant so that only X and Y vary with time. (a) Show that if all rate constants are chosen appropriately, the equations de scribing a Brusselator are: dt A-(B+ 1)x + x²y, dy =Bx-x²y. diarrow_forwardProblem 3. Provide a mechanism for the following transformation: H₂SO A Me. Me Me Me Mearrow_forwardYou are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: xi 1. ☑ 2. H₂O хе i Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. There is no reagent that will make this synthesis work without complications. : ☐ S ☐arrow_forward
- Predict the major products of this organic reaction: H OH 1. LiAlH4 2. H₂O ? Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. G C टेarrow_forwardFor each reaction below, decide if the first stable organic product that forms in solution will create a new C-C bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. NH2 CI MgCl ? Will the first product that forms in this reaction create a new CC bond? Yes No MgBr ? Will the first product that forms in this reaction create a new CC bond? Yes No G टेarrow_forwardFor each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. དྲ。 ✗MgBr ? O CI Will the first product that forms in this reaction create a new C-C bond? Yes No • ? Will the first product that forms in this reaction create a new CC bond? Yes No × : ☐ Xarrow_forward
- Predict the major products of this organic reaction: OH NaBH4 H ? CH3OH Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. ☐ : Sarrow_forwardPredict the major products of this organic reaction: 1. LIAIHA 2. H₂O ? Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. X : ☐arrow_forwardFor each reaction below, decide if the first stable organic product that forms in solution will create a new C - C bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. NH2 tu ? ? OH Will the first product that forms in this reaction create a new CC bond? Yes No Will the first product that forms in this reaction create a new CC bond? Yes No C $ ©arrow_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