ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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Chapter 18.5, Problem 5CC

(a)

Interpretation Introduction

Interpretation:

The expected product(s) have to be predicted when benzene is treated with following alkyl halides in presence of AlCl3

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 18.5, Problem 5CC , additional homework tip  1

Concept Introduction:

  • Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions. An electrophile is a species that is deficient of electrons.
  • Aromatic compounds agree with Huckel’s rule of aromaticity - cyclic, planar and have (4n+2)π electrons. 
  • Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compound. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • The carbocation formed in Benzene ring Carbon is known as arenium carbocation. It is also known as sigma complex. It is the intermediate involved in all the aromatic electrophilic substitution reactions of benzene and related compounds.  It is stabilized by delocalization of pi electrons which is also known as resonance.
  • Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves C-C bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.
  • Any of Lewis acids such as AlCl3,FeCl3,BF3etc is required to initiate the reaction. The Lewis acid act as catalyst assists in the formation of electrophile.  The reaction between Alkyl halide and Lewis acid results in the formation of alkyl ion as electrophile.

(b)

Interpretation Introduction

Interpretation:

The expected product(s) have to be predicted when benzene is treated with following alkyl halides in presence of AlCl3

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 18.5, Problem 5CC , additional homework tip  2

Concept Introduction:

  • Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions. An electrophile is a species that is deficient of electrons.
  • Aromatic compounds agree with Huckel’s rule of aromaticity - cyclic, planar and have (4n+2)π electrons. 
  • Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compound. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • The carbocation formed in Benzene ring Carbon is known as arenium carbocation. It is also known as sigma complex. It is the intermediate involved in all the aromatic electrophilic substitution reactions of benzene and related compounds.  It is stabilized by delocalization of pi electrons which is also known as resonance.
  • Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves C-C bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.
  • Any of Lewis acids such as AlCl3,FeCl3,BF3etc is required to initiate the reaction. The Lewis acid act as catalyst assists in the formation of electrophile.  The reaction between Alkyl halide and Lewis acid results in the formation of alkyl ion as electrophile.

(c)

Interpretation Introduction

Interpretation:

The expected product(s) have to be predicted when benzene is treated with following alkyl halides in presence of AlCl3

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 18.5, Problem 5CC , additional homework tip  3

Concept Introduction:

  • Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions. An electrophile is a species that is deficient of electrons.
  • Aromatic compounds agree with Huckel’s rule of aromaticity - cyclic, planar and have (4n+2)π electrons. 
  • Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compound. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • The carbocation formed in Benzene ring Carbon is known as arenium carbocation. It is also known as sigma complex. It is the intermediate involved in all the aromatic electrophilic substitution reactions of benzene and related compounds.  It is stabilized by delocalization of pi electrons which is also known as resonance.
  • Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves C-C bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.
  • Any of Lewis acids such as AlCl3,FeCl3,BF3etc is required to initiate the reaction. The Lewis acid act as catalyst assists in the formation of electrophile.  The reaction between Alkyl halide and Lewis acid results in the formation of alkyl ion as electrophile.

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f. Predict how the van Deemter curve in Figure 7 would change if the temperature were raised from 40 °C to 55 °C. Figure 7. van Desmter curves in reduced coordinates for four nitroalkane homologues (nitropropane, black; nitrobutane, red; nitropentane, blue; and nitrohexane, green) separated on the FMS phase. Chromatographic conditions: column dimensions 50 mm × 4.6 mm id, eluent 30/70 ACN/water, flow rates 0.2-5.0 mL/min, injection volume 0.5 and column temperature 40 °C. No corrections to the plate heights have been made to account for extracolumn dispersion. Reduced Plate Height (h) ° 20 40 60 Reduced Velocity (v) 8. (2) A water sample is analyzed for traces of benzene using headspace analysis. The sample and standard are spiked with a fixed amount of toluene as an internal standard. The following data are obtained: Ppb benzene Peak area benzene Peak area toluene 10.0 252 376 Sample 533 368 What is the concentration of benzene in the sample?
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