Homework Help is Here – Start Your Trial Now!
Science
Chemistry
classify the two groups attached to the ring in salicylamide as activators or deactivators. Then classify the directing effects of the two groups.

classify the two groups attached to the ring in salicylamide as activators or deactivators. Then classify the directing effects of the two groups.

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter24: Catalytic Carbon-carbon Bond Formation
Section: Chapter Questions
Problem 24.25P: It is typically very difficult to do a substitution reaction on an aromatic ring when the leaving...
See similar textbooks
icon
Related questions
Question
100%

Please help, I keep getting this question wrong-

classify the two groups attached to the ring in salicylamide as activators or
deactivators. Then classify the directing effects of the two groups. thanks in advance

Synthesis of lodosalicylamide - An Electrophilic Aromatic Substitution Introduction Benzene can undergo certain types of reactions known as electrophilic aromatic substitutions (EAS). As the name implies, some atom or small molecule substitutes onto the benzene ring in place of a hydrogen atom. In today's experiment, we will be using a derivative of benzene, salicylamide, and substituting an iodine atom onto the ring. In all EAS reactions, the ring is the nucleophile while the atom/molecule that is being substituted onto the ring must have electrophilic character. Groups already present on the ring can either activate or deactivate the ring. Another way to think about this is that activating groups can speed up the rate of reaction while deactivating groups slow down the reaction. Activating groups will donate electron density into the ring and will specifically activate it's ortho and para positions. This is why we classify them as ortho, para directors. Deactivating groups will withdraw electron density from the ring. This electron withdrawing effect deactivates the ortho para positions towards nucleophilic attack, which in turn directs the substitution to its meta position. This is why deactivating groups are meta directors. The only exception to this statement is the halogens. The halogens do deactivate the ring, but they also can donate an electron pair into the ring via resonance. Therefore, halogens will be ortho para directing but deactivate the ring. Your organic lecture textbook and your instructor will have discussed this in further detail in lecture. More resources regarding these types of reactions can be found under this week's resources on Brightspace. The overall reaction is shown below. The line going through the benzene ring connected to iodine is a type of shorthand that can be used when you're unsure of the exact location of the substituent on the ring. As far as the exact location of the substitution, you'll need to predict based on your knowledge of the types of activating/deactivating groups already substituted on salicylamide. NH₂ OH 1)Nal, NaOCI, CH CH.OH 2) NaySO HCL NH₂ OH As a quick reference, the mechanism for the electrophilic aromatic substitution is shown below The electrophile, It, is generated from 12. The nucleophile, the pi electrons of the ring, attacks I and loses aromaticity, forming a sigma complex. This sigma complex is a resonance stabilized carbocation intermediate. The ring will then regain aromaticity once it is deprotonated by a base.
Transcribed Image Text:Synthesis of lodosalicylamide - An Electrophilic Aromatic Substitution Introduction Benzene can undergo certain types of reactions known as electrophilic aromatic substitutions (EAS). As the name implies, some atom or small molecule substitutes onto the benzene ring in place of a hydrogen atom. In today's experiment, we will be using a derivative of benzene, salicylamide, and substituting an iodine atom onto the ring. In all EAS reactions, the ring is the nucleophile while the atom/molecule that is being substituted onto the ring must have electrophilic character. Groups already present on the ring can either activate or deactivate the ring. Another way to think about this is that activating groups can speed up the rate of reaction while deactivating groups slow down the reaction. Activating groups will donate electron density into the ring and will specifically activate it's ortho and para positions. This is why we classify them as ortho, para directors. Deactivating groups will withdraw electron density from the ring. This electron withdrawing effect deactivates the ortho para positions towards nucleophilic attack, which in turn directs the substitution to its meta position. This is why deactivating groups are meta directors. The only exception to this statement is the halogens. The halogens do deactivate the ring, but they also can donate an electron pair into the ring via resonance. Therefore, halogens will be ortho para directing but deactivate the ring. Your organic lecture textbook and your instructor will have discussed this in further detail in lecture. More resources regarding these types of reactions can be found under this week's resources on Brightspace. The overall reaction is shown below. The line going through the benzene ring connected to iodine is a type of shorthand that can be used when you're unsure of the exact location of the substituent on the ring. As far as the exact location of the substitution, you'll need to predict based on your knowledge of the types of activating/deactivating groups already substituted on salicylamide. NH₂ OH 1)Nal, NaOCI, CH CH.OH 2) NaySO HCL NH₂ OH As a quick reference, the mechanism for the electrophilic aromatic substitution is shown below The electrophile, It, is generated from 12. The nucleophile, the pi electrons of the ring, attacks I and loses aromaticity, forming a sigma complex. This sigma complex is a resonance stabilized carbocation intermediate. The ring will then regain aromaticity once it is deprotonated by a base.
08-6-3-6 sigma complex During this reaction, a series of three redox reactions will take place. Color changes of the reaction mixture will be observed as the different redox reactions take place. In the first redox reaction, the iodide ion (from Nal) reacts with hypochlorite in the presence of three protons to form iodine (12). 12 is the source of I*, the electrophile in the EAS reaction. Some of the iodide ion is left behind and will combine with 12 which forms la. The thiosulfate ion is then added to reduce la to water soluble 1¹ which stops the reaction. Redox Reactions: (1) CIO¹+ 41¹³ + 3H→ HCI +H₂O + 2 12 (red) 1₂ +1¹²¹13¹¹ (yellow/green) 13 +25₂03 → 31¹ +OS-S-S-SO (2) (3) Our reactant and product this week can be analyzed by investigating the fingerprint region of the IR. Substitution pattern on aromatic rings can be found in the region between 700 and 900 cm depending on how the groups are arranged. You should be able to determine the substitution pattern of your product easily by examining this region. The vibration arises from the C-H bend from the aromatic ring called the "C-H oop." The different substitution patterns and their corresponding expected peaks are listed below. 715-770 (strong) 730-770 (strong) 750 790 (strangh o od 760-820 (strong) 800-850 (strong) 830-910 (strong) 800-870 (strong)
Transcribed Image Text:08-6-3-6 sigma complex During this reaction, a series of three redox reactions will take place. Color changes of the reaction mixture will be observed as the different redox reactions take place. In the first redox reaction, the iodide ion (from Nal) reacts with hypochlorite in the presence of three protons to form iodine (12). 12 is the source of I*, the electrophile in the EAS reaction. Some of the iodide ion is left behind and will combine with 12 which forms la. The thiosulfate ion is then added to reduce la to water soluble 1¹ which stops the reaction. Redox Reactions: (1) CIO¹+ 41¹³ + 3H→ HCI +H₂O + 2 12 (red) 1₂ +1¹²¹13¹¹ (yellow/green) 13 +25₂03 → 31¹ +OS-S-S-SO (2) (3) Our reactant and product this week can be analyzed by investigating the fingerprint region of the IR. Substitution pattern on aromatic rings can be found in the region between 700 and 900 cm depending on how the groups are arranged. You should be able to determine the substitution pattern of your product easily by examining this region. The vibration arises from the C-H bend from the aromatic ring called the "C-H oop." The different substitution patterns and their corresponding expected peaks are listed below. 715-770 (strong) 730-770 (strong) 750 790 (strangh o od 760-820 (strong) 800-850 (strong) 830-910 (strong) 800-870 (strong)
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 4 steps with 3 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Reactions at the Alpha Carbon Atom
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
SEE MORE TEXTBOOKS