Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 10.SE, Problem 18MP
Draw the electron-pushing mechanism for the propagation steps of the allylic bromination reactions below. You may omit NBS in your mechanism, and use Br ∙ and Br2.
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5a) Draw the product(s) of the reaction shown below. Additionally, identify the nucleophile, electrophile and leaving group.
4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain,
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ỌMe
Na, MeOH
?
NH3
CHO
Na, MeOH
?
NH3
2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but
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of negative charge needed to be a good nucleophile.
CH3CH₂O
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CH3SO3
H₂O
CH₂OH
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
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- Draw the mechanism and the energy diagram for the reaction shown below. Include any resonance structures for the intermediates of the reaction. H3O+arrow_forwardDraw the product for the substitution reactions below. Then, draw the proper FULL electron-pushing mechanism for the reaction, including intermediates with lone pairs and formal charges, and all electron pushing arrows (SN1 vs SN2). Label the electrophile and nucleophile in each step.arrow_forwardDecide which compounds from the list below are best suited for nucleophilic addition reactions and which ones are more appropriate for nucleophilic substitution reactions.arrow_forward
- Draw a detailed, step-wise mechanism for the reaction shown below. SHOW ALL BOND-FORMING AND BOND-BREAKING STEPS. SHOW ALL INTERMEDIATES. 1) NaOH 2) H3O* H3C H3C HOarrow_forwardDraw all resonance structures for the carbocation formed by ortho attack of the electrophile +NO2 on attached starting material. Label any resonance structures that are especially stable or unstablearrow_forward6) Write the mechanism (two propagation steps only, starting with the bromine radical in the first step and using Br2 in the second step) and that would explain how the following two products are produced. (Hint – the allylic radical is resonance stabilized.) Br Br NBSarrow_forward
- 3) Any compound or ion with at least one lone pair can be considered a base and/or a nucleophile. The relative basicity and nucleophilicity of the species is one of the most important factors that determine the mechanism of a reaction on sp³-carbon atoms. Please show an example of a) a reagent that is a strong nucleophile and a strong base, b) a reagent that is a weak nucleophile and a strong base, c) a reagent that is a strong nucleophile and a weak base, d) a reagent that is a weak nucleophile and a weak base. Which nitrogen atom in the structure below is most nucleophilic? Please explain by discussing the electron density around each nitrogen atom. Show at least three resonance structures of the compound. N.arrow_forwardGive 3 examples of a reaction mechanism of E1 that follows Zaitsev's rule.arrow_forwardDraw the product of an SN2 reaction shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. Br Bu4NCI DMF Draw SN2 productarrow_forward
- 2- Mention the product of a nucleophilic substitution reaction of (S)-2-bromohexane with acetate ion, CH3CO2- Assume that inversion of configuration occurs, and show the chemistry of both the reactant and product. 3- Draw the mechanism of the SN2 Reaction. Show the correct directions of the arrows, and all reagents. 4- Draw the mechanism of the SN1 Reaction. Show the correct directions of the arrows, and all reagents. 5- Draw the mechanism of the E2 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 6- Draw the mechanism of the E1 Reaction with an Alkyl Halide. Show the correct directions of the arrows, and all reagents. 7- Mention the product formed in an SN2 reaction between 1-bromobutane and NaI. 8- Rank the following compounds in order of their expected reactivity toward SN2 reaction: CH3Br, CH3OTos, (CH3)2CHCl. 9- Explain Grignard Reagents in details with one example. 10- Mention how a halogen substituent can be replaced by a deuterium atom…arrow_forwardDraw a step-wise mechanism for the following substitution reaction. Be sure to add lone pairs and charges where relevant. CH,OH Br 3arrow_forward5. Predict whether each reaction will occur via SN2 or E2 mechanism and draw the product. Write 'NR' if the reaction will not proceed as written. & CH3CI NaCl Acetone KOt-Bu t-BuOH KOt-Bu t-BuOH NaOEt EtOHarrow_forward
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