ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
4th Edition
ISBN: 9781119659556
Author: Klein
Publisher: WILEY
Question
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Chapter 18, Problem 54PP

 (a)

Interpretation Introduction

Interpretation:

The given following flaw in the synthesis has to be identified.

Concept Introduction:

  • Electrophiles are electron deficient species. In Electrophilic substitution reaction a group or atom in a compound is replaced by electrophile. This kind of reaction occurs predominantly in aromatic compounds. Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions.
  • Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction. 
  • The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • If the substituents on benzene Carbon are Electron rich groups they are known as activating groups. They are ortho- and para- directing groups because these groups when directly bonded to benzene Carbon increases the electron density at ortho and para positions. So they direct the incoming electrophile towards ortho and para position in electrophilic substitution reactions.
  • If the substituents on benzene Carbon are Electron withdrawing groups they are known as deactivating groups. They are meta-directing groups because these groups when directly bonded to benzene Carbon decreases the electron density at ortho and para positions and so the incoming electrophile is directed towards meta position.
  • Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

(b)

Interpretation Introduction

Interpretation:

The given following flaw in the synthesis has to be identified.

Concept Introduction:

  • Electrophiles are electron deficient species. In Electrophilic substitution reaction a group or atom in a compound is replaced by electrophile. This kind of reaction occurs predominantly in aromatic compounds. Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions.
  • Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction. 
  • The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • If the substituents on benzene Carbon are Electron rich groups they are known as activating groups. They are ortho- and para- directing groups because these groups when directly bonded to benzene Carbon increases the electron density at ortho and para positions. So they direct the incoming electrophile towards ortho and para position in electrophilic substitution reactions.
  • If the substituents on benzene Carbon are Electron withdrawing groups they are known as deactivating groups. They are meta-directing groups because these groups when directly bonded to benzene Carbon decreases the electron density at ortho and para positions and so the incoming electrophile is directed towards meta position.
  • Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

(c)

Interpretation Introduction

Interpretation:

The given following flaw in the synthesis has to be identified.

Concept Introduction:

  • Electrophiles are electron deficient species. In Electrophilic substitution reaction a group or atom in a compound is replaced by electrophile. This kind of reaction occurs predominantly in aromatic compounds. Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions.
  • Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction. 
  • The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • If the substituents on benzene Carbon are Electron rich groups they are known as activating groups. They are ortho- and para- directing groups because these groups when directly bonded to benzene Carbon increases the electron density at ortho and para positions. So they direct the incoming electrophile towards ortho and para position in electrophilic substitution reactions.
  • If the substituents on benzene Carbon are Electron withdrawing groups they are known as deactivating groups. They are meta-directing groups because these groups when directly bonded to benzene Carbon decreases the electron density at ortho and para positions and so the incoming electrophile is directed towards meta position.
  • Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

 (d)

Interpretation Introduction

Interpretation:

The given following flaw in the synthesis has to be identified.

Concept Introduction:

  • Electrophiles are electron deficient species. In Electrophilic substitution reaction a group or atom in a compound is replaced by electrophile. This kind of reaction occurs predominantly in aromatic compounds. Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions.
  • Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction. 
  • The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • If the substituents on benzene Carbon are Electron rich groups they are known as activating groups. They are ortho- and para- directing groups because these groups when directly bonded to benzene Carbon increases the electron density at ortho and para positions. So they direct the incoming electrophile towards ortho and para position in electrophilic substitution reactions.
  • If the substituents on benzene Carbon are Electron withdrawing groups they are known as deactivating groups. They are meta-directing groups because these groups when directly bonded to benzene Carbon decreases the electron density at ortho and para positions and so the incoming electrophile is directed towards meta position.
  • Friedel-Crafts Alkylation: This Lewis acid-catalyzed electrophilic aromatic replacement allows the synthesis of alkylated products by means of the reaction of arenes through alkyl halides or alkenes.

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A student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from the arrow. • Is the student's transformation possible? If not, check the box under the drawing area. . If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts, inorganic reagents, or other important reaction conditions above and below the arrow. • You do not need to balance the reaction, but be sure every important organic reactant or product is shown. + T X O O лет-ле HO OH HO OH This transformation can't be done in one step.
Determine the structures of the missing organic molecules in the following reaction: X+H₂O H* H+ Y OH OH Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. X S
Predict the major products of this organic reaction. If there aren't any products, because nothing will happen, check the box under the drawing area instead. No reaction. HO. O :☐ + G Na O.H Click and drag to start drawing a structure. XS xs H₂O
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