Organic Chemistry, 6th edition Paula Yurkanis Bruice

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Presentation transcript:

Organic Chemistry, 6th edition Paula Yurkanis Bruice Chapter 15 Aromaticity Reactions of Benzene Brian L. Groh Minnesota State University, Mankato Mankato, MN Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.1 The difference in energy between “cyclohexatriene” and benzene is __kcal/mol. +49.8 +28.8 -28.8 -36.0 -85.8 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.1 The difference in energy between “cyclohexatriene” and benzene is __kcal/mol. +49.8 +28.8 -28.8 -36.0 -85.8 Benzene is 36.0 kcal/mol more stable than the theoretical cyclohexatriene. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Assuming planarity, which of the following molecules is aromatic? 15.3 Assuming planarity, which of the following molecules is aromatic? Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Assuming planarity, which of the following molecules is aromatic? 15.3 Assuming planarity, which of the following molecules is aromatic? This is a 4n + 2 pi electron system. The lone pair of electrons on the nitrogen atom are perpendicular to the pi electrons and cannot interact with them. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.7 Which of the following molecular orbital diagrams best fits that of pyrrole? pyrrole A B C D E None of the above Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.7 Which of the following molecular orbital diagrams best fits that of pyrrole? pyrrole A B C The lone pair of electrons on the nitrogen atom are included with the pi electrons to give a 4n+2 pi electron system. E None of the above Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.10 Which of the following statements regarding electrophilic aromatic substitution is incorrect? Halogenation: Br, Cl, or I substitutes for a hydrogen. Nitration: -NH2 substitutes for a hydrogen. Sulfonation: -SO3H substitutes for a hydrogen. Friedel–Crafts acylation: RC=O (acyl) substitutes for a hydrogen. Friedel–Crafts alkylation: R (alkyl) substitutes for a hydrogen. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.10 Which of the following statements regarding electrophilic aromatic substitution is incorrect? Halogenation: Br, Cl, or I substitutes for a hydrogen. Nitration: -NH2 substitutes for a hydrogen. Sulfonation: -SO3H substitutes for a hydrogen. Friedel–Crafts acylation: RC=O (acyl) substitutes for a hydrogen. Friedel–Crafts alkylation: R (alkyl) substitutes for a hydrogen. Nitration involves –NO2 substitution. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.14-15.16 Which combination of reagents is best suited to prepare n-propylbenzene? Benzene, CH3CH2CH2Cl, AlCl3 catalyst Benzene, CH3CH=CH2, HF catalyst Benzene, 1. CH3CH2COCl, AlCl3 cat. 2. Zn(Hg) HCl Benzene, CH3CH2CH2OH, H2SO4 Chlorobenzene, CH3CH=CH2, AlCl3 catalyst Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.14-15.16 Which combination of reagents is best suited to prepare n-propylbenzene? Benzene, CH3CH2CH2Cl, AlCl3 catalyst Benzene, CH3CH=CH2, HF catalyst Benzene, 1. CH3CH2COCl, AlCl3 cat. 2. Zn(Hg) HCl Benzene, CH3CH2CH2OH, H2SO4 Chlorobenzene, CH3CH=CH2, AlCl3 catalyst Attempted direct alkylation (“A”) using a primary halide will result in rearrangement of the carbocation intermediate. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.17 Which combination of reagents is acceptable for the preparation of n-propylbenzene? Bromobenzene, (CH3CH2CH2)2CuLi (Gillman) Bromobenzene, (CH3CH2CH2)4Sn, PdL2 cat. (Stille) Bromobenzene, RO2B(CH2)2CH3, PdL2, HO- (Suzuki) Propyl bromide, (C6H5)2CuLi (Gillman) Any of the above Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.

Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. 15.17 Which combination of reagents is acceptable for the preparation of n-propylbenzene? Bromobenzene, (CH3CH2CH2)2CuLi (Gillman) Bromobenzene, (CH3CH2CH2)4Sn, PdL2 cat. (Stille) Bromobenzene, RO2B(CH2)2CH3, PdL2, HO- (Suzuki) Propyl bromide, (C6H5)2CuLi (Gillman) Any of the above Organometallic mediated coupling reactions are very versatile. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.