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 41AP
Interpretation Introduction
Interpretation:
The faster reactant is to be identified from SN2 reaction with OH-.
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,
CH3I and CH3Br
b.
The given compound is shown below,
CH3CH2I in ethanol and CH3CH2I in dim ethylsulf oxide (DMSO)
c.
The given compound is shown below,
(CH3)3CCl and CH3Cl
d.
The given compound is shown below,
CH2 = CH2 Br or CH2 = CHCH2Br
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
11) What sequence of reactions would best accomplish the following conversion?
O
O
CH3CCH2CH
?
OH
O
||
I
CH3CHCH2CH
In an SN2 reaction between 2-chlorobutane and iodide ion, what happens to the rate of the reaction if:
(a) the concentration of 2-chlorobutane is doubled?
(b) the concentration of iodide is doubled?
What is the correct sequence of steps for the following transformation?
Step 1
Step 2
HO
(a) HBr, followed by H20
(b) H2 over Lindlar's catalyst, followed by H2O/H,SO4
(c) H2O/H2SO4/H&SO4, followed by HBr
(d) H2 over Pd/C, followed by H20
Which structure corresponds to the missing step in the reaction mechanism for the
conversion of the alkene/alcohol to the cyclic ether?
HC!
H20
+ H;O
OH
OH
OH
(a)
(b)
(c)
(d)
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
- If anhydrides react like acid chlorides with the nucleophiles, draw the products formed when each of the following nucleophiles reacts with benzoic anhydride [(C6H5CO)2O]: (a) CH3MgBr (2 equiv), then H2O; (b) LiAlH4, then H2O; (c) LiAlH[OC(CH3)3]3, then H2O.arrow_forward6-40 Give the substitution products expected from solvolysis of each compound by heating in ethanol. (a) (b) (c) Br (d) Br CI CH3 Brarrow_forwardWhat is the product of the following two-step reaction sequence? Hint: count carbons! он OH (a) (b) он step 1: heat HO, step 2: NABH, OH он (c) (d)arrow_forward
- Provide the mechanism for the following reaction (1) PhMgBr (2 equiv) (2) H3O+ workup OHarrow_forwardWhich of the following compounds is the major product of the reaction sequenc shown below? (1) Na CNCH3CN Br (A) (B) NH2 (2) H* H20, A он (C) (D) HO. O Compound C )Compound A Compound D )Compound Barrow_forward8. Which of the following alkyl halide undergo rearrangement in S reaction ? 'N CH 3 Cl (а) CHз — С- СH-CH3 (b) (d) All of these (c) CH3 CH3 Iarrow_forward
- Which compound in each of the following pairs will react faster in SN2 reaction with —OH?(i) CH3Br or CH3I (ii) (CH3)3 CCl or CH3Clarrow_forwardWrite the appropriate reagents, conditions and products for the following transformations, in a single step. OH II HNO, ? (1) H,SO,arrow_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_forward
- 1) Provide the reagent(s) and the reaction mechanism of the following reaction. H₂Narrow_forwardWhich of the following is the best method to carry out the following transformation? OH (a) H₂SO4, H₂O (b) 1. BH3 2. H₂O2, OH (c) 1. Hg(OAc)₂2 H₂O 2. NaBH. (d) 1. HBr 2. H₂Oarrow_forward6-46 Show how each compound might be synthesized by the SN2 displacement of an alkyl halide. SCH,CH, (a) -CH₂OH (c) (d) CHÍNH, 6-47 (a) Give twn synthecac fox (CI) qu (b) (e) H₂C=CH-CH₂CN n OLL BU (1) H-C=C-CH₂CH₂CH₂arrow_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