ORGANIC CHEMISTRY-STUDY GDE...-W/ACCESS
4th Edition
ISBN: 9780078051555
Author: SMITH
Publisher: MCG
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Chapter 7, Problem 7.82P
Interpretation Introduction
(a)
Interpretation: The product of the given two-step sequence reaction is to be drawn.
Concept introduction: Nucleophilic substitution reactions are those reactions, in which a nucleophile attacks at the electrophilic site and displaces the good leaving group.
The rate determining step in
Interpretation Introduction
(b)
Interpretation: The product of the given two-step sequence reaction is to be drawn.
Concept introduction: Nucleophilic substitution reactions are those reactions, in which a nucleophile attacks at the electrophilic site and displaces the good leaving group.
The rate determining step in
Interpretation Introduction
(c)
Interpretation: The product of the given two-step sequence reaction is to be drawn.
Concept introduction: Nucleophilic substitution reactions are those reactions, in which a nucleophile attacks at the electrophilic site and displaces the good leaving group.
The rate determining step in
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Chapter 7 Solutions
ORGANIC CHEMISTRY-STUDY GDE...-W/ACCESS
Ch. 7 - Classify each alkyl halide as 1 , 2, or 3.Ch. 7 - Problem 7.1 Telfairine, a naturally occurring...Ch. 7 - Draw the structure of an alkyl bromide with...Ch. 7 - Give the IUPAC name for each compound. a. b. c. d.Ch. 7 - Prob. 7.5PCh. 7 - An sp3 hybridized CCl bond is more polar than an...Ch. 7 - Prob. 7.7PCh. 7 - Problem 7.6 Identify the nucleophile and leaving...Ch. 7 - Prob. 7.9PCh. 7 - Prob. 7.10P
Ch. 7 - Prob. 7.11PCh. 7 - Prob. 7.12PCh. 7 - Does the equilibrium favor the reactants or...Ch. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Classify each solvent as protic or aprotic. a. b....Ch. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Draw an energy diagram for the reaction in Problem...Ch. 7 - Draw the product of each SN2 reaction and indicate...Ch. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 7 - What happens to the rate of an SN1 reaction under...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Classify each carbocation as 1,2, or 3. a. b. c....Ch. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Which alkyl halide in each pair reacts faster in...Ch. 7 - Prob. 7.32PCh. 7 - Problem 7.30 For each alkyl halide and...Ch. 7 - Prob. 7.34PCh. 7 - Prob. 7.35PCh. 7 - Prob. 7.36PCh. 7 - Prob. 7.37PCh. 7 - Prob. 7.38PCh. 7 - Prob. 7.39PCh. 7 - Prob. 7.40PCh. 7 - Prob. 7.41PCh. 7 - Give the IUPAC name for each compound, including...Ch. 7 - Draw the products formed when each alkyl halide is...Ch. 7 - Give the IUPAC name for each compound. a. c....Ch. 7 - Prob. 7.45PCh. 7 - Classify each alkyl halide in Problem 7.44 as 1 ,...Ch. 7 - Draw the eight constitutional isomers having the...Ch. 7 - Prob. 7.48PCh. 7 - Draw the substitution product that results when...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 7.51PCh. 7 - Rank the species in each group in order of...Ch. 7 - Which of the following nucleophilic substitution...Ch. 7 - Prob. 7.54PCh. 7 - Prob. 7.55PCh. 7 - Prob. 7.56PCh. 7 - 7.53 Consider the following reaction.
Draw a...Ch. 7 - Prob. 7.58PCh. 7 - Prob. 7.59PCh. 7 - Draw the products of each SN2 reaction and...Ch. 7 - Prob. 7.61PCh. 7 - Prob. 7.62PCh. 7 - Prob. 7.63PCh. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - Prob. 7.65PCh. 7 - Prob. 7.66PCh. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 7.68PCh. 7 - Prob. 7.69PCh. 7 - Diphenhydramine, the antihistamine in Benadryl,...Ch. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 7.73PCh. 7 - Prob. 7.74PCh. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 7.76PCh. 7 - Fill in the appropriate reagent or starting...Ch. 7 - Devise a synthesis of each compound from an alkyl...Ch. 7 - Prob. 7.79PCh. 7 - Suppose you have compounds A-D at y our disposal....Ch. 7 - Prob. 7.81PCh. 7 - Prob. 7.82PCh. 7 - Prob. 7.83PCh. 7 - Prob. 7.84PCh. 7 - 7.80 As we will learn in Chapter 9, an epoxide is...Ch. 7 - Prob. 7.86PCh. 7 - In some nucleophilic substitutions under SN1...
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- The SN1 mechanism starts with the rate-determining step which is the dissociation of the alkyl halide into a carbocation and a halide ion. The next step is the rapid reaction of the carbocation intermediate with the nucleophile; this step completes the nucleophilic substitution stage. The step that follows the nucleophilic substitution is a fast acid-base reaction. The nucleophile now acts as a base to remove the proton from the oxonium ion from the previous step, to give the observed product. Draw a curved arrow mechanism for the reaction, adding steps as necessary. Be sure to include all nonzero formal charges.arrow_forwardshow the missing reagents and intermediates in the reaction sequence belowarrow_forwardSeveral reagents and several organic structures are shown below. Construct a multistep synthetic route from the reactant 2-methyl-1-butene to the product 3-bromo-2-methyl-2-butanol by dragging the appropriate pieces into the bins. Note that each bin will hold only one item, and not every given reagent or structure will be used.arrow_forward
- Can you help answer this problem and elaborate the steps clearly and show any reagent and intermediate steps?arrow_forwardDraw the molecule: Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other.Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2∘∘ alkyl halide) with sodium ethoxide. Do not worry about sterechemistry inther SN2 product for this problem. Don't forget about stereochemistry.arrow_forwardAlcohols react with sulfonyl chlorides to form sulfonate esters. Only the O-H bond of the alcohol is broken in the reaction, and so no inversion of configuration occurs. The resulting sulfonate esters are reactive in SN1 and SN2 reactions since the sulfonate group is a very weak base and is therefore a good leaving group.Draw curved arrows to show the movement of electrons in this step of the mechanism.arrow_forward
- Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methyl butane (a moderately hindered 2∘ alkyl halide) with sodium ethoxide. Do not worry about stereochemistry in the SN2 product for this problem. Don't forget about stereochemistry.arrow_forwardWhat would the final product look like? Show the mechanism using acid catalyzed tautomerization to achieve final product arrow_forwardBiaryls, compounds containing two aromatic rings joined by a C–C bond, can often be efficiently made by two different Suzuki couplings; that is, either aromatic ring can be used to form the organoborane needed for coupling. In some cases, however, only one route is possible. With this in mind, synthesize each of the following biaryls using benzene as the starting material for each aromatic ring. When more than one route is possible, draw both of them. You may use any required organic or inorganic reagents.arrow_forward
- For each of the questions below – determine whether the following combinations of reactants, will react by substitution (SN1 or SN2 mechanism), elimination (E1 or E2 mechanism) or will not react under the conditions given. draw the final structure and explain the logic for each decision. There may be multiple possible options for some reactions. You must include all 4 aspects of these reactions, substrate, nucleophile, solvent and leaving group in the decisionarrow_forwardWhen the allylic alkyl bromide shown below is heated in ethanol solvent, the major elimination product isolated is the diene shown below. A) Propose a mechanism to account for this overall transformation. Use normal curved arrows to show movement of electron pairs and be sure to draw structures for all important reaction intermediates. If an intermediate is a resonance hybrid, draw all important contributing resonance structures. B) The same alkyl bromide shown above also yields several substitution products when subjected the reaction conditions described above. Draw the structure of the major substitution product that would be isolated in the box on the product side of the reaction arrow. The second picture is for the B part of the questionarrow_forwardComplete the following reaction schemes. Some may take more than one step and some may have several routes to the product.arrow_forward
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