ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN
4th Edition
ISBN: 9781119760924
Author: Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 7.7, Problem 16ATS
Interpretation Introduction
Interpretation:
The E2 product for each given compound must be drawn and which compound is more stable must be identified with the explanation.
Concept introduction:
E2 reaction is a concerted bimolecular elimination reaction in which both substrate and base are involved in the rate-determining step. A stable compound is less reactive, and it contains lesser energy as compared to an unstable compound.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The following compound reacts with NaOMe in an SN2 reaction. Draw the transition state
and the final product of the reaction and use the transition state geometry to explain the
stereochemical outcome of the reaction. What is the side-reaction that might occur and
what would be the major product of that reaction?
Br
NaOMe
ČH3
Draw the product of the following SN2 reaction, including the stereochemistry at all stereogenic centers. The product of this reaction is aprepitant, a drug used to treat nausea and emesis (vomiting) in chemotherapy patients.
The bicyclo [3.1.0] hexane ring system, highlighted in compound 3, is found in several natural products, including sabinene, a compound partially responsible for the flavor of ground black pepper. One method for preparing this ring system involves the conversion of compound 1 to compound 2, as shown below. Draw the structure of compound 2 and provide a reasonable mechanism for its formation.
What are the most likely steps in the mechanism to form product 2?
a. protonate, protonate, nucleophilic attack, nucleophilic attack
b. Nucleophilic attack, protonate, protonate, nucleophilic attack
c. Nucleophilic attack, protonate, nucleophilic attack, protonate
d. Protonate, nucleophilic attack, protonate, nucleophilic attack
Chapter 7 Solutions
ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN
Ch. 7.2 - Prob. 1CCCh. 7.3 - Prob. 2CCCh. 7.3 - Prob. 1LTSCh. 7.3 - Prob. 3PTSCh. 7.3 - Prob. 4ATSCh. 7.3 - Prob. 2LTSCh. 7.3 - Prob. 5PTSCh. 7.3 - Prob. 6ATSCh. 7.3 - Prob. 7CCCh. 7.4 - Prob. 8CC
Ch. 7.5 - Prob. 9CCCh. 7.6 - Prob. 10CCCh. 7.6 - Prob. 11CCCh. 7.7 - Prob. 12PTSCh. 7.7 - Prob. 13PTSCh. 7.7 - Prob. 14ATSCh. 7.7 - Prob. 4LTSCh. 7.7 - Prob. 16ATSCh. 7.7 - Prob. 17CCCh. 7.7 - Prob. 18CCCh. 7.7 - Prob. 5LTSCh. 7.7 - Prob. 19PTSCh. 7.7 - Prob. 20ATSCh. 7.8 - Prob. 21PTSCh. 7.8 - Prob. 22ATSCh. 7.8 - Prob. 23CCCh. 7.8 - Prob. 24CCCh. 7.8 - Prob. 25CCCh. 7.8 - Prob. 26CCCh. 7.8 - Prob. 27CCCh. 7.9 - Prob. 7LTSCh. 7.9 - Prob. 29ATSCh. 7.9 - Prob. 30ATSCh. 7.9 - Prob. 31ATSCh. 7.10 - Prob. 32CCCh. 7.10 - Prob. 33CCCh. 7.10 - Prob. 34CCCh. 7.11 - Prob. 8LTSCh. 7.11 - Prob. 35PTSCh. 7.11 - Prob. 36PTSCh. 7.11 - Prob. 37ATSCh. 7.11 - Prob. 9LTSCh. 7.11 - Prob. 40PTSCh. 7.11 - Prob. 41ATSCh. 7.12 - Prob. 42CCCh. 7.12 - Prob. 43CCCh. 7.12 - Prob. 44CCCh. 7.12 - Prob. 45CCCh. 7.12 - Prob. 46CCCh. 7 - Prob. 47PPCh. 7 - Prob. 48PPCh. 7 - Prob. 49PPCh. 7 - Prob. 50PPCh. 7 - Prob. 51PPCh. 7 - Prob. 52PPCh. 7 - Prob. 53PPCh. 7 - Prob. 54PPCh. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - Prob. 58PPCh. 7 - Prob. 59PPCh. 7 - Prob. 60PPCh. 7 - Prob. 61PPCh. 7 - Prob. 64PPCh. 7 - Indicate whether you would use NaOEt or tBuOK to...Ch. 7 - Prob. 68PPCh. 7 - Draw a plausible mechanism for each of the...Ch. 7 - Prob. 70PPCh. 7 - Prob. 71PPCh. 7 - Prob. 72PPCh. 7 - Prob. 73PPCh. 7 - Prob. 74PPCh. 7 - Prob. 77PPCh. 7 - Prob. 78PPCh. 7 - Prob. 81ASPCh. 7 - Prob. 87ASPCh. 7 - Prob. 90ASPCh. 7 - Prob. 91IPCh. 7 - Prob. 92IPCh. 7 - Prob. 93IPCh. 7 - Prob. 94IPCh. 7 - Prob. 95IPCh. 7 - Prob. 96IPCh. 7 - Prob. 97IPCh. 7 - Prob. 98IPCh. 7 - Prob. 99IPCh. 7 - Prob. 100IPCh. 7 - Prob. 101IPCh. 7 - Prob. 102IPCh. 7 - Prob. 103IPCh. 7 - Prob. 105IPCh. 7 - Prob. 106IPCh. 7 - Prob. 107IPCh. 7 - Prob. 109IPCh. 7 - Prob. 110CPCh. 7 - Prob. 112CPCh. 7 - Prob. 114CP
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
- Q11. Draw all the possible chair-like conformations of compounds 1-2. In the presence of a strong base, compound 1 undergoes an elimination following an E2 mechanism to generate the most substituted and thermodynamically most favoured alkene 3, while compound 2 generates the less stable alkene 4. Knowing that the E2 mechanism requires the two leaving groups to be antiperiplanar, use the chair-like structures of compounds 1 and 2 to justify this difference in reactivity. CH3 CH3 Br E2 more stable alkene 1 3 CH3 CH3 Br E2 less stable alkene 4arrow_forwardSN2 Substitution. The following compound reacts with NaOMe in an SN2 reaction. Draw the transition state and the final product of the reaction and use the transition state geometry to explain the stereochemical outcome of the reaction Br NaOMearrow_forwardHow many rings and π bonds are contained in compounds A–C? Draw one possible structure for each compound. a. Compound A has molecular formula C5H18 and is hydrogenated to a compound having molecular formula C510H10. b. Compound B has molecular formula C10H16 and is hydrogenated to a compound having molecular formula C10H18. c. Compound C has molecular formula C8H8 and is hydrogenated to a compound having molecular formula C8H16.arrow_forward
- How many rings and π bonds are contained in compounds A–C? Draw one possible structure for each compound. a. Compound A has molecular formula C5H8 and is hydrogenated to a compound having molecular formula C5H10.b. Compound B has molecular formula C10H16 and is hydrogenated to a compound having molecular formula C10H18.c. Compound C has molecular formula C8H8 and is hydrogenated to a compound having molecular formula C8H16.arrow_forward(2R,3S)-2-Bromo-3-phenylbutane undergoes an E2 elimination when treated with sodium methoxide. Draw all possible Newman projections for the bond relevant for the elimination reaction, and use those Newman projections to explain the stereochemical outcome of the reaction. Draw the final product and provide its IUPAC name.arrow_forwardThe following bicyclic ketone has two a-carbons and three a-hydrogens. When this molecule is treated with D,O in the presence of an acid catalyst, only two of the three a-hydrogens exchange with deuterium. The a-hydrogen at the bridgehead does not exchange. H these two a-hydrogens exchange H. this a-hydrogen does not exchange H How do you account for the fact that two a-hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of a-hydrogens occurs.arrow_forward
- H3C N- H₂NNH₂ H⭑ CH3 H3C IN CH3 Hydrazine reacts with 2,4-pentanedione to yield 3,5-dimethylpyrazole. Including protonations and deprotonations, the reaction takes 12 steps. Write out the mechanism on a sheet of paper and then draw the structure of the product of step 6. • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • In an elimination step, include the structure of the leaving group, but draw it in its own sketcher. Separate structures with + signs from the drop-down menu. ? Sn th Previous Nextarrow_forwardDraw an Energy diagram for an E1 reaction: (CH3)3CI + H2O ⇢ (CH3)2C=CH2+ H3O+ + I−arrow_forwardDraw all the major products resulting from the reactions below, taking into consideration both the regioselectivity and stereoselectivity of the reactions. If pairs of enantiomers form, draw both enantiomers. Br₂ CH3CH₂OH (in large excess) H₂, Pd/Carrow_forward
- 7. Compound X is an antibacterial drug of the sulfonamide group, and was widely used in the mid-20th century as one of the earliest antimicrobial drugs. X is synthesized through the following sequence of reactions. Draw structures of A-C and X, and show mechanism for the reaction C to X. NO2 NO2 1) NaNO2, H*, H20 H202 NH3 B H2 NaSH > X ZrCl4 Pd 2) O=S=0 H2N `NH2 NH2arrow_forwardDraw the structure of a 1°, 2°, and 3° carbocation, each having molecular formula C4H9+. Rank the three carbocations in order of increasing stability.arrow_forwardWhich of the given compound is most reactive towards E2 elimination? CI H3C, ICH3 H3C CI H3C CI H3C "CH3 H3C CH3 CI H3Carrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning