Aromatic heterocycles can undergo electrophilic aromatic substitution like benzene. Groups attached to the heterocycle can therefore have similar directing effects as they can on benzene. Keeping this in mind, consider the following reaction, where E+ is a general electrophile: a) Draw all relevant resonance structures for the intermediate of each product b) Based on your answers to part a), which product do you expect to be the major product and why? (2 points) c) If you performed this reaction in the laboratory, which instrumental technique (ex: 1H NMR, IR, Mass Spectrometry) would be best to determine which product you obtained of the three and why?

Aromatic heterocycles can undergo electrophilic aromatic substitution like benzene. Groups attached to the heterocycle can therefore have similar directing effects as they can on benzene. Keeping this in mind, consider the following reaction, where E+ is a general electrophile: a) Draw all relevant resonance structures for the intermediate of each product b) Based on your answers to part a), which product do you expect to be the major product and why? (2 points) c) If you performed this reaction in the laboratory, which instrumental technique (ex: 1H NMR, IR, Mass Spectrometry) would be best to determine which product you obtained of the three and why?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 7CTQ

See similar textbooks

Similar questions

Hint: think about carbocation stability of benzylic carbocations vs. simple tertiary carbocations b. НО cat. H,SO4 EtОH НО cat. H2SO4 EtОH A Mechanism: Product of faster reaction: Reason: Il..
c) Rank the following compounds in order of increasing reactivity toward nucleophiles. Explain your reasoning briefly with reference to structural features. or wy CI A
Predict the major organic product of the given reaction. Select Draw Rings More 1. NaOEt/ETOH 2. CH3CH2CH2Br 3. dilute NaOH/heat 4. H3O* 5. Нeat d orrow mechanism for the scheme by adding any missing atoms, bonds, charges,
OCHEM Help with reactions Please provide the major product for A, B, and C of the following reaction...
Enamines can act as carbon nucleophiles and react with acyl chlorides. Draw any non-bonding electrons or cnarges on the structure of the enamine provided below, then using curved arrows provide a step by step mechanism showing any intermediates along the reaction pathway for the acylation reaction with benzoyl chloride to yield the product. C -t.. f..Jl mal.- enamine
2. Consider the following reaction. MeOH CI b. Predict the stereochemistry of the final product(s). OMe a. Provide a reasonable arrow-pushing mechanism for the following reaction, showing all steps and balancing all charges. c. Label the electrophilic sites on the molecule and explain why only one of undergoes substitution.
Kinetic and thermodynamic enol products Of 2-butanone conditions? Factors that affect Rate of reaction?...
final product. b) Draw the correct first step and complete the mechanism, showing the structure of the HO: H. H. НО-Н H. H. .. reaction. H. H a) Explain why the following mechanism is not plausible for the first step of this 2. Consider the following reaction:
3,) you have now eliminated one substitution site and should have two possible sites remaining. Provide a mechanism for the formation of each of the two remaining products. You should include all possible. Resident structures for the cat on intermediates. There should be four resident structures in each mechanism. You do not need to show the mechanism for the formation of the electrify you may assume that only a single iodine will add to the ring. a. b. GOLDEST GAD SE 1029 OH H OH 02AB o 1o1 meiasdoorn woms bevis song of olds pel I+ noboibong tombong 10 to asiqisminoviowTill bris H₂O, EtOH naut nobibba as gada tasest 30 no odt to toubong Input sdr lo notaxillaryn I+ bouborg on to ving di salmsibb or O etshqoqs edt onimaob or atob MM O bax H seu zie.baz anoitecu dale19 H₂O, EtOH lliw gan snated a no quorg lanoituut invellib.noimadue shamore siliqotools al Hoib blaos tad aquosy Insoitonut oor za milline V.mobest ad not sila noistade sitt lenoiraut dues bleno) nobedog ad to goitool…
Which of the following is a limitation of the Friedel-Crafts reaction? Select one: O A. The carbocation electrophile can potentially undergo an unwanted rearrangement prior to its bonding to the aromatic ring. OB. Poly-alkylation products form when aromatic reactant and alkylating agent are mixed together in comparable amounts. OC. A Friedel-Crafts reaction fails when the aromatic starting compound contains a moderately or strongly deactivating group. OD. All of the above choices are limitations of the Friedel-Crafts reaction.
Synthesis - Drawing Saved Synthesize the following compound from cyclohexanol, ethanol, and any other needed reagents. он Part 1 out of 2 plnts Preparation of organometallic reagent: еВook Print References A B CH3CH2OH CH3 CH2MGB. draw structure ... Draw the intermediate product above and select the correct reagent for A. O Br, O NaBr O HBr O Select the correct reagent for B. O Mg O MgBr2 O MgI, O MgO Hin Soluti raw 11 e here to search
3. (Sections 19.6 and 19.7) Draw the mechanism for the Wolff-Kishner reaction in a., being sure to show all relevant lone pairs, charges, arrows, etc. Draw the major product formed in reactions b. and c. For all reactions, pay attention to stereochemistry and regiochemistry! jose H 1) H2N-NH2, acetic acid, H₂O/diethylene glycol 2) NaOH, 200 °C CH3 a. b. C=N H₂O H2SO4 CEN H₂O NaOH