Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 6.13B, Problem 6.24P
3-Bromocyclohexene is a secondary halide, and benzyl bromide is a primary halide Both halides undergo SN1 substitution about as fast as most tertiary halides Use resonance structures to explain this enhanced reactivity.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
3-Bromocyclohexene is a secondary halide, and benzyl bromide is a primary halide. Both halides undergo SN1 substitution about as fast as most tertiary halides. Use resonance structures to explain this enhanced reactivity.
Cinnamoyl chloride (C9H7CIOO) can be prepared by the two-step sequence shown below.
Reaction 1: C7H60 + CAH6O3 C9H8O2 + C2H402
Reaction 2: C9H&O2 + SOC2 → C9H7oci + sO2 + HCI
CH60 C4H6O3 C9H8O2 C2H402 SOCI2 C9H,Oci SO2
HCI
Molar masses
106.12 102.09
148.16
60.05
118.96
166.60
64.07 36.46
(in g mol-1)
What is the percent atom economy for the synthesis of cinnamoyl chloride? Enter an answer accurate to three
significant figures.
Number
Nucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate
called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving
group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure
via resonance.
For the reaction below, draw the structure of the stabilized reaction intermediate in the box below.
CI
F3C
CF3
NO₂
F3C
N
CF3
NO₂
• You do not have to consider stereochemistry.
• Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than
one resonance structure is possible, only draw the most important one.
Chapter 6 Solutions
Organic Chemistry (9th Edition)
Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4PCh. 6.4 - Prob. 6.5PCh. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7PCh. 6.6B - Prob. 6.8PCh. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...
Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Practice Problem 1.22 Which of the following alkenes can exist as cis-trans isomers? Write their structures. Bu...
Organic Chemistry
For each of the following 2-dimensional shapes, determine the highest order rotation axis of symmetry.
Inorganic Chemistry
Consider a sample of ideal gas initially in a volume V at temperature T and pressure P. Does the entropy of thi...
General Chemistry: Principles and Modern Applications (11th Edition)
Give one example from main group chemistry that illustrates each of the following descriptions: (a) Covalent ne...
General Chemistry: Atoms First
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (14th Edition)
Characterize each of the following structures as aromatic, nonaromatic, or antiaromatic:
Answer: _____
Organic Chemistry As a Second Language: Second Semester Topics
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
- In the presence of excess base and excess halogen, a methyl ketone is converted to a carboxylate ion. The reaction is known as the haloform reaction because one of the products is haloform (chloroform, bromoform, or iodoform). Before spectroscopy became a routine analytical tool, the haloform reaction served as a test for methyl ketones: the formation of iodoform, a bright yellow compound, signaled that a methyl ketone was present. Why do only methyl ketones form a haloform?arrow_forwardDiphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forwardRank the following alkyl halides in term of reactivity in a E2 reaction with NaOH (fastest (1) to slowest (4)): 1-bromo-2,2-dimethylpentane, 1-chloro-2,2-dimethylpentane, 2-chloro-2-methylpentane, and 2-bromo-2-methylpentane.arrow_forward
- 1) Complete the following reaction and provide a detailed, step-by-step mechanism for the process. HBr 2) Provide the structure of the major organic product in the reactions below. HI CH3 win H3C. CH3 CH₂CH3 HCI Xero H₂C CH3 HBrarrow_forwardProvide the curved-arrow mechanism to account for the following nucleophilic addition reaction. H20 EN NaOH NH2arrow_forward4) Provide a complete step by step mechanism for the following reactions. + HCC13 Peroxide, Joubong sitwa CC13arrow_forward
- Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:arrow_forwardPredict the coupling products of organometallic substitutions, and use them in syntheses.arrow_forwardAn enolate is a very strong nucleophile. Bromine is a strong electrophile, so it can react withmuch weaker nucleophiles. Give mechanisms for the reactions of bromine with cyclopenteneand with phenol, which are both much weaker nucleophiles than an enolatearrow_forward
- List the following in increasing order of nucleophilic strength. CH3COO-, H2O, CH3O-, OH-, CH3CH20-arrow_forwardWhich of the following reaction sequences would be best for converting compound I to compound II? OCH3 Br Compound I Το OCH3 Compound IIarrow_forward2-bromo-2-methylbutane with sodium methoxide under SN2/E2 conditions substitution product elimination product both substitution and elimination products no productsarrow_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 LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples 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 EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary 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
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License