
(a)
Interpretation: For the given compounds, major products should be predicted when each of them are treated with Birch condition.
Concept introduction:
- Birch reduction converts
aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene. - The product having hydrogen atoms attached on opposite end of the molecule
- Birch reduction is the reduction of aromatic rings with sodium , potassium or lithium and an alcohol in liquid ammonia
- Birch reduction is unlike catalytic hydrogenation
- When the benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion.
- When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.
(b)
Interpretation: For the given compounds, major products should be predicted when each of them are treated with Birch condition.
Concept introduction:
- Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene.
- The product having hydrogen atoms attached on opposite end of the molecule
- Birch reduction is the reduction of aromatic rings with sodium , potassium or lithium and an alcohol in liquid ammonia
- Birch reduction is unlike catalytic hydrogenation
- When the benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion.
- When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.
(c)
Interpretation: For the given compounds, major products should be predicted when each of them are treated with Birch condition.
Concept introduction:
- Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene.
- The product having hydrogen atoms attached on opposite end of the molecule
- Birch reduction is the reduction of aromatic rings with sodium , potassium or lithium and an alcohol in liquid ammonia
- Birch reduction is unlike catalytic hydrogenation
- When the benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion.
- When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.
(d)
Interpretation: For the given compounds, major products should be predicted when each of them are treated with Birch condition.
Concept introduction:
- Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene.
- The product having hydrogen atoms attached on opposite end of the molecule
- Birch reduction is the reduction of aromatic rings with sodium , potassium or lithium and an alcohol in liquid ammonia
- Birch reduction is unlike catalytic hydrogenation
- When the benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion.
- When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.
(e)
Interpretation: For the given compounds, major products should be predicted when each of them are treated with Birch condition.
Concept introduction:
- Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene.
- The product having hydrogen atoms attached on opposite end of the molecule
- Birch reduction is the reduction of aromatic rings with sodium , potassium or lithium and an alcohol in liquid ammonia
- Birch reduction is unlike catalytic hydrogenation
- When the benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion.
- When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.
(f)
Interpretation: For the given compounds, major products should be predicted when each of them are treated with Birch condition.
Concept introduction:
- Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene.
- The product having hydrogen atoms attached on opposite end of the molecule
- Birch reduction is the reduction of aromatic rings with sodium , potassium or lithium and an alcohol in liquid ammonia
- Birch reduction is unlike catalytic hydrogenation
- When the benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron donating effect destabilizes the radical anion.
- When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing effect stabilizes the intermediate.

Want to see the full answer?
Check out a sample textbook solution
Chapter 18 Solutions
Organic Chemistry, Binder Ready Version
- H-Br Energy 1) Draw the step-by-step mechanism by which 3-methylbut-1-ene is converted into 2-bromo-2-methylbutane. 2) Sketch a reaction coordinate diagram that shows how the internal energy (Y- axis) of the reacting species change from reactants to intermediate(s) to product. Brarrow_forward2. Draw the missing structure(s) in each of the following reactions. The missing structure(s) can be a starting material or the major reaction product(s). C5H10 H-CI CH2Cl2 CIarrow_forwardDraw the products of the stronger acid protonating the other reactant. དའི་སྐད”“ H3C OH H3C CH CH3 KEq Product acid Product basearrow_forward
- Draw the products of the stronger acid protonating the other reactant. H3C NH2 NH2 KEq H3C-CH₂ 1. Product acid Product basearrow_forwardWhat alkene or alkyne yields the following products after oxidative cleavage with ozone? Click the "draw structure" button to launch the drawing utility. draw structure ... andarrow_forwardDraw the products of the stronger acid protonating the other reactant. H3C-C=C-4 NH2 KEq CH H3C `CH3 Product acid Product basearrow_forward
- 2. Draw the missing structure(s) in each of the following reactions. The missing structure(s) can be a starting material or the major reaction product(s). C5H10 Br H-Br CH2Cl2 + enant.arrow_forwardDraw the products of the stronger acid protonating the other reactant. KEq H₂C-O-H H3C OH Product acid Product basearrow_forwardDraw the products of the stronger acid protonating the other reactant. OH KEq CH H3C H3C `CH3 Product acid Product basearrow_forward
- 2. Draw the missing structure(s) in each of the following reactions. The missing structure(s) can be a starting material or the major reaction product(s). Ph H-I CH2Cl2arrow_forward3 attempts left Check my work Draw the products formed in the following oxidative cleavage. [1] 03 [2] H₂O draw structure ... lower mass product draw structure ... higher mass productarrow_forward2. Draw the missing structure(s) in each of the following reactions. The missing structure(s) can be a starting material or the major reaction product(s). H-Br CH2Cl2arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





