Organic Chemistry As a Second Language: Second Semester Topics
4th Edition
ISBN: 9781119110651
Author: David R. Klein
Publisher: WILEY
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Question
Chapter 4.6, Problem 4.31P
Interpretation Introduction
Interpretation:
The expected directing effects that would be observed if the given compound undergoes an electrophilic
Concept Introduction:
Electrophilic substitution reaction is a type of reaction in which a particular group or atom in a compound is replaced by electrophile. An electrophile is a species that is deficient of electrons
Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.
Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho-para directing.
Halogens are deactivators that are ortho-para directing.
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Which of the following compound be the more reactive in an electrophilic aromatic substitution reaction?
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Draw the structure of the compound whose data is shown below
C9H9NO3
There are 7 C-NMR signals. The compound is significantly deactivated toward
electrophilic aromatic substitution.
H-NMR:
12.7 ppm, s, 1H
10.3 ppm, s 1H
7.91 ppm, d, 2H
7.72 ppm, d, 2H
2.10 ppm, s 3H
Chapter 4 Solutions
Organic Chemistry As a Second Language: Second Semester Topics
Ch. 4.1 - Consider the following reaction, in which an...Ch. 4.1 - Prob. 4.3PCh. 4.1 - Aromatic rings will also undergo iodination when...Ch. 4.2 - In each of the following cases, identify the...Ch. 4.2 - In each of the following cases, identify the...Ch. 4.2 - In each of the following cases, identify the...Ch. 4.3 - Prob. 4.10PCh. 4.3 - Prob. 4.11PCh. 4.3 - Prob. 4.12PCh. 4.3 - Prob. 4.13P
Ch. 4.3 - Prob. 4.14PCh. 4.3 - Predict the products of the following reaction.Ch. 4.3 - Prob. 4.16PCh. 4.3 - Prob. 4.17PCh. 4.4 - Identify the reagents you would use to achieve...Ch. 4.4 - Identify the reagents you would use to achieve...Ch. 4.4 - Identify the reagents you would use to achieve...Ch. 4.4 - Identify the reagents you would use to achieve...Ch. 4.4 - fill in the reagents you would use for the...Ch. 4.4 - fill in the reagents you would use for the...Ch. 4.4 - fill in the reagents you would use for the...Ch. 4.4 - fill in the reagents you would use for the...Ch. 4.4 - Prob. 4.27PCh. 4.4 - Prob. 4.28PCh. 4.4 - And now, for a challenging problem, try to draw...Ch. 4.6 - Prob. 4.31PCh. 4.6 - Prob. 4.32PCh. 4.6 - Prob. 4.33PCh. 4.6 - Prob. 4.34PCh. 4.6 - Prob. 4.35PCh. 4.6 - Prob. 4.36PCh. 4.6 - Prob. 4.37PCh. 4.6 - Prob. 4.40PCh. 4.6 - Prob. 4.41PCh. 4.6 - Predict the products for each of the following...Ch. 4.6 - Predict the products for each of the following...Ch. 4.6 - Predict the products for each of the following...Ch. 4.6 - Predict the products for each of the following...Ch. 4.6 - Prob. 4.47PCh. 4.6 - Prob. 4.48PCh. 4.6 - Prob. 4.49PCh. 4.6 - Prob. 4.50PCh. 4.6 - Prob. 4.51PCh. 4.6 - Prob. 4.52PCh. 4.6 - Prob. 4.53PCh. 4.6 - Prob. 4.54PCh. 4.6 - Prob. 4.55PCh. 4.6 - Prob. 4.56PCh. 4.7 - Prob. 4.58PCh. 4.7 - Prob. 4.59PCh. 4.7 - Prob. 4.60PCh. 4.7 - Prob. 4.61PCh. 4.7 - Prob. 4.62PCh. 4.7 - Prob. 4.63PCh. 4.7 - Prob. 4.64PCh. 4.7 - Prob. 4.65PCh. 4.7 - Prob. 4.66PCh. 4.7 - Prob. 4.67PCh. 4.7 - Can you explain why the following group is a...Ch. 4.7 - Prob. 4.70PCh. 4.7 - Prob. 4.71PCh. 4.7 - Prob. 4.72PCh. 4.7 - Prob. 4.73PCh. 4.7 - Prob. 4.74PCh. 4.7 - Prob. 4.76PCh. 4.7 - Prob. 4.77PCh. 4.7 - Prob. 4.78PCh. 4.7 - Prob. 4.79PCh. 4.8 - Propose an efficient synthesis for each of the...Ch. 4.8 - Propose an efficient synthesis for each of the...Ch. 4.8 - Propose an efficient synthesis for each of the...Ch. 4.8 - Propose an efficient synthesis for each of the...Ch. 4.8 - Propose an efficient synthesis for each of the...Ch. 4.8 - Prob. 4.87PCh. 4.8 - Prob. 4.88PCh. 4.8 - Prob. 4.89PCh. 4.8 - Prob. 4.90PCh. 4.8 - Prob. 4.91PCh. 4.8 - Prob. 4.92PCh. 4.9 - Prob. 4.94PCh. 4.9 - Prob. 4.95PCh. 4.9 - Prob. 4.96PCh. 4.9 - Prob. 4.97PCh. 4.9 - Prob. 4.98PCh. 4.9 - Prob. 4.99PCh. 4.9 - Prob. 4.100PCh. 4.9 - Prob. 4.101PCh. 4.9 - Prob. 4.102P
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Similar questions
- Determine which nucleophilic aromatic substitutions are likely, and proposemechanisms for both the addition–elimination type and the benzyne type.arrow_forwardWhich among the given compounds is being described by the following statements? Choose your answer from the BRIGHT WIN TINE Activates the ring towards electrophilic aromatic substitution and directs an electrophile to the para position: Deactivates the ring towards electrophilic aromatic substitution and directs an electrophile to the ortho position: Deactivates the ring towards electrophilic aromatic substitution and directs an electrophile to the meta position:arrow_forwardShow how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.arrow_forward
- Draw the structure of the compound whose data is shown below. Upload your answer to receive full credit. C9H,NO3 There are 7 C-NMR signals. The compound is significantly deactivated toward electrophilic aromatic substitution. H-NMR: 12.7 ppm, s, 1H 10.3 ppm, s 1H 7.91 ppm, d, 2H 7.72 ppm, d, 2H 2.10 ppm, s 3Harrow_forwardDescribe how an electron withdrawing group on an aromatic ring affects the proton chemical shifts of the aromatic protons.arrow_forwardWhich benzene derivative would be the most reactive in an electrophilic aromatic substitution reaction? NO2arrow_forward
- Provide the steps to convert the following aldehyde to the given amine product.arrow_forwardShow how to synthesize each of the following compounds using only a single nucleophilic aromatic substitution reaction. (a) NO, (b) (c) NO2 O,N ноarrow_forwardDetermine whether each of the following compounds can function as a suitable electrophile in a nucleophilic aromatic substitution reaction. NO₂ Ef O-S-CH3 I NO₂ Br X NO₂arrow_forward
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