Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 11.SE, Problem 46AP
Interpretation Introduction
Interpretation:
The faster reactant is to be identified from given pairs of reactants with given reagent.
Concept introduction:
SN2 reaction:
Tosylated compound is reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,
Given information:
a.
The given compound is shown below,
The SN2 displacement by I- on CH3Cl and CH3OTos
b.
The given compound is shown below,
The SN2 displacement by CH3COO- on bromoethane or on Bromo cyclohexane.
c.
The given compound is shown below,
The SN2 displacement on 2-bromopropane by CH3CH2O- or by CN-
d.
The given compound is shown below,
The SN2 displacement by CH ≡ C- on bromomethane in benzene or in acetonitrile
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
10) What is the major product of the following reactions?
CH3
+
HCI
H₂O
H*
?
CH3CO3 H
HBr
11) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-
methylcyclohexene? Explain.
What product(s) is/are formed when the following compound react with ozone and then with dimethyl sulfide
(i.e. ozonolysis)?
a)
b)
What product(s) would you expect to obtain from reaction of 1, 3-cyclohexadiene witheach of the following?(a) 1 mol Br2in CH2Cl2(b) O3followed by Zn(c) 1 mol HCl in ether(d) 1 mol DCl in ether(e) 3-Buten-2-one (H2C = CHCOCH3)(f) Excess OsO4, followed by NaHSO3
6. Write the IUPAC name for the following compounds. Show the stereochemistry whenever required
(a)
HO
NH2
CI
(b)
NH2 QH
но
(c)
он
Br
H.
(d)
(e)
OH
Br
Br
Chapter 11 Solutions
Organic Chemistry
Ch. 11.1 - Prob. 1PCh. 11.2 - Prob. 2PCh. 11.2 - Prob. 3PCh. 11.3 - Prob. 4PCh. 11.3 - Prob. 5PCh. 11.3 - Rank the following compounds in order of their...Ch. 11.3 - Organic solvents like benzene, ether, and...Ch. 11.4 - Prob. 8PCh. 11.4 - Prob. 9PCh. 11.4 - Prob. 10P
Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
Knowledge Booster
Similar questions
- 7В. (2 Draw the structure of the product, substrate or condition in the following reactions (should clearly indicate the stereochemistry). (а) OH (b) OsO vaHSO3 (c) 1) (sia)2 BH 2) NaOH/H,O2 H20 (d) HBr (2 equiv) Br, Br Hint: This is the only product formed (e) Br Br2 H20 OH (f)arrow_forwardNaOCH3 (S)-1-chloro-1,2-diphenylethane مين من cis-1,2-diphenylethene trans-1,2-diphenylethene + NaCl + HOCH 3 (a) Disregarding stereochemistry for the moment, provide a curved arrow mechanism for the transformation of the starting alkyl halide to one of the products.arrow_forward(i) OEt OEt 1) NaOEt 2) H3O* workup W 1) NaOEt 2) Br V Compound W can be synthesised in an excellent yield via an intramolecular Claisen reaction of 1,6-diester V. Draw the structure of product W and provide detailed reactions mechanisms to account for its formation. (ii) Draw the product X which would form upon the alkylation reaction of W with the reagents shown.arrow_forward
- 11. Plan syntheses of the following compounds. You may use the given starting material and any compound containing five or fewer carbons. (a) MeO MeO CN TOXXON anything with five or fewer carbons. CN (b) (c)arrow_forwardQ12. (1-bromoethyl)benzene 1 udergoes an elimination following an E1 mechanism. Fill in the following synthetic scheme by drawing the structure of intermediate 2 and product 3. The chemical formula of product 3 is provided as guidance. CH; RDS Br C3Hg E1 2 3arrow_forwardYour task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents would you use? O KOH/H2O O KOH/CH,OH O CH3CH2ONA/CH3CH2OH O CH3ONA/CH3OH O (CH3)3COK/(CH3)3COHarrow_forward
- Q4. Discuss the reagents, conditions, and mechanism of the following reactions. a) Kolbe Reaction b) Williamson synthesis c) Reimer Tiemann reactionarrow_forwardProvide the structure(s) of the expected major organic product of the reaction shown. 1) Disiamylborane 2) H₂O₂, NaOH OI O II ||| O IV OV CH3CH₂C(CH3)2C=CH OH OH xx xo IVarrow_forwardOrder the compounds in each set according to their sn2-displacement reactivity:1-bromobutane; 1-bromo-2,2-dimethylpropane; 1-bromo-2-methylbutane; 1-bromo-3-methylbutane.arrow_forward
- What effect would you expect the following changes to have on the rate of the Sy2 reaction of 1-iodo-2-methylbutane with cyanide ion? (a) The CN- concentration is halved, and the l-iodo-2-methylbutane con- centration is doubled. (b) Both the CN- and the 1-iodo-2-methylbutane concentrations are tripled.arrow_forwardWhen 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutanearrow_forwardWhen 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observedarrow_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