Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 6.4, Problem 5P
An electrostatic potential map of boron trifluoride is shown. Is BF3 likely to be a nucleophile or an electrophile? Draw a Lewis structure for BF3, and explain your answer.
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Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown.
Note: You do not need to draw any of the side products of the reaction, only the substitution product.
□
+
HO
1
+ X
S
Click and drag to start
drawing a structure.
Consider the following:
Why is the oxygen atom selectively protonated?
A) Oxygen is less electronegative than nitrogen.
B) The six-membered ring becomes aromatic when protonated.
C) Oxygen is a better electrophile.
D) Better stabilization by resonance.
4-pyranone will readily undergo an acid-base reaction.
Identify the reaction conditions that will result in the
formation of an aromatic product. Then, draw the
aromatic resonance product structure.
Include all lone pairs in your structure. Ignore inorganic
byproducts.
H3O+
Chapter 6 Solutions
Organic Chemistry
Ch. 6.1 - Prob. 1PCh. 6.3 - Prob. 2PCh. 6.3 - Using curved fishhook arrows, propose a mechanism...Ch. 6.4 - Prob. 4PCh. 6.4 - An electrostatic potential map of boron...Ch. 6.5 - What product would you expect from reaction of...Ch. 6.5 - Reaction of HBr with 2-methylpropene yields...Ch. 6.6 - Prob. 8PCh. 6.6 - Predict the products of the following polar...Ch. 6.7 - Which reaction is more energetically favored, one...
Ch. 6.7 - Prob. 11PCh. 6.9 - Which reaction is faster, one with ∆G‡ = +45...Ch. 6.10 - Prob. 13PCh. 6.SE - Prob. 14VCCh. 6.SE - Prob. 15VCCh. 6.SE - Prob. 16VCCh. 6.SE - Look at the following energy diagram: (a) Is...Ch. 6.SE - Look at the following energy diagram for an...Ch. 6.SE - What is the difference between a transition state...Ch. 6.SE - Prob. 20EDRMCh. 6.SE - Prob. 21EDRMCh. 6.SE - Draw an energy diagram for a two-step exergonic...Ch. 6.SE - Draw an energy diagram for a reaction with keq =...Ch. 6.SE - The addition of water to ethylene to yield ethanol...Ch. 6.SE - When isopropylidenecyclohexane is treated with...Ch. 6.SE - Prob. 26EDRMCh. 6.SE - Draw the electron-pushing mechanism for each...Ch. 6.SE - Draw the complete mechanism for each polar...Ch. 6.SE - Prob. 29EDRMCh. 6.SE - Identify the functional groups in the following...Ch. 6.SE - Identify the following reactions as additions,...Ch. 6.SE - Identify the likely electrophilic and nucleophilic...Ch. 6.SE - For each reaction below identify the electrophile...Ch. 6.SE - Prob. 34APCh. 6.SE - Follow the flow of electrons indicated by the...Ch. 6.SE - Prob. 36APCh. 6.SE - Prob. 37APCh. 6.SE - Despite the limitations of radical chlorination of...Ch. 6.SE - Prob. 39APCh. 6.SE - Answer question 6-39 taking all stereoisomers into...Ch. 6.SE - Prob. 41APCh. 6.SE - Prob. 42APCh. 6.SE - Prob. 43APCh. 6.SE - The reaction of hydroxide ion with chloromethane...Ch. 6.SE - Prob. 45APCh. 6.SE - Ammonia reacts with acetyl chloride (CH3COCl) to...Ch. 6.SE - The naturally occurring molecule α-terpineol is...Ch. 6.SE - Prob. 48APCh. 6.SE - Prob. 49APCh. 6.SE - Draw the structures of the two carbocation...
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- Nitration of an aromatic ring involves an electrophilic substitution reaction. Draw the structure of the electrophile that is attacked by the aromatic ring and the intermediate formed after attachment of the electrophile to the ring. Be sure to show formal charges.arrow_forwardDraw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. H × 5 Br + HO + 1 Click and drag to start drawing a structure.arrow_forwardBriefly, but clearly, explain why the –OH hydrogen in acetic acid (CH3CO2H) is more acidic than in ethanol (C2H5OH).arrow_forward
- A certain hydrocarbon had the molecular formula C18H30 and contained two triple bonds. Ozonolysis gave CH₂(CH₂)CO₂H and HO₂CCH₂CH₂CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure.arrow_forwardWhen the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forward4. a)Nucleophiles. Define a "nucleophile" in organic chemistry? b) Identifying nucleophiles. Bronsted-Lowry acid-base pairs are shown. Which one in each pair can serve as a nucleophile.in an organic nucleohilic reaction. (Explain your choice.) It is helpful sometimes to draw in all the lone-pairs of electrons. or H-Br or Br H3O+ i or H₂O 요 or CEN H-CEN O=C=0 or O-CEN CH3NH2 CH3NH3+ OH orarrow_forward
- C1. Subject :- Chemistryarrow_forward3. Please draw the most important (stable) resonance form of the carbonation that mediates the following reaction: OH H3O+ O 4. Draw the structure of the alkene isomer (with the molecular formula of C5H10) that is most reactive one in the addition reaction with Br₂.arrow_forwardOH 1. NaOH, EtOH 2. n-BuBr A nucleophilic substitution reaction is a frequently used method to convert one functional group into another. A nucleophile is mixed with an electrophile and the nucleophile replaces the leaving group to produce a new compound. In this experiment, a weak nucleophile (2-naphthol) is converted into a strong nucleophile by deprotonation with sodium hydroxide. Then this strong nucleophile, now with a negative charge, reacts with alkyl halide to yield an ether, 2-butoxynaphthalene. 2-butoxynaphthalene is a flavoring agent that has strong fruit smell like raspberry and strawberry.arrow_forward
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