Question 1

Which would be the major product(s)of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) I and II in roughly equal amounts. 
E) I and III in roughly equal amounts. 
A) I 
B) II 
C) III 
D) I and II in roughly equal amounts. 
E) I and III in roughly equal amounts.

Question 2

Which is the best sequence of reactions for the following transformation?

Accepted Answer

A) i)HNO3,H2SO4; ii)CH3MgBr,Et2O; iii)H3O+,heat 
B) i)CH3MgBr,Et2O; ii)H3O+,heat; iii)HNO3,H2SO4 
C) i)HNO3,H2SO4; ii)NaBH4,H2O; iii)H3O+,heat 
D) i)HNO3,H2SO4; ii)LiAlH4,H2O; iii)H3O+,heat 
E) None of these syntheses is satisfactory. 
A) i)HNO3,H2SO4; ii)CH3MgBr,Et2O; iii)H3O+,heat 
B) i)CH3MgBr,Et2O; ii)H3O+,heat; iii)HNO3,H2SO4 
C) i)HNO3,H2SO4; ii)NaBH4,H2O; iii)H3O+,heat 
D) i)HNO3,H2SO4; ii)LiAlH4,H2O; iii)H3O+,heat 
E) None of these syntheses is satisfactory.

Question 3

What would you expect to be the major product obtained from the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 4

What feature is common to all meta-directing groups?

Accepted Answer

A) The atom directly attached to the ring has a full or well-developed partial positive charge. 
B) The atom directly attached to the ring is doubly bonded to oxygen. 
C) One or more halogen atoms are present in the group. 
D) One or more oxygen atoms are present in the group. 
E) The group is attached to the ring through a carbon atom. 
A) The atom directly attached to the ring has a full or well-developed partial positive charge. 
B) The atom directly attached to the ring is doubly bonded to oxygen. 
C) One or more halogen atoms are present in the group. 
D) One or more oxygen atoms are present in the group. 
E) The group is attached to the ring through a carbon atom.

Question 5

What is a feature found in all ortho-para directing groups?

Accepted Answer

A) An oxygen atom is directly attached to the aromatic ring. 
B) The atom attached to the aromatic ring must possess an unshared pair of electrons. 
C) The group has the ability to delocalize the positive charge of the arenium ion. 
D) The atom directly attached to the aromatic ring is more electronegative than carbon. 
E) The group contains a multiple bond. 
A) An oxygen atom is directly attached to the aromatic ring. 
B) The atom attached to the aromatic ring must possess an unshared pair of electrons. 
C) The group has the ability to delocalize the positive charge of the arenium ion. 
D) The atom directly attached to the aromatic ring is more electronegative than carbon. 
E) The group contains a multiple bond.

Question 6

Propose a reasonable synthesis of the following compound from benzene.

Accepted Answer

The answer of Propose a reasonable synthesis of the following...

Question 7

Benzoic acid can be prepared by the oxidation of which of the following compounds:

Accepted Answer

A) C6H5CH=CH2 
B) C6H5C$\equiv$CH 
C) C6H5COCH3 
D) C6H5CH(CH3)2 
E) All of these choices. 
A) C6H5CH=CH2 
B) C6H5C$\equiv$CH 
C) C6H5COCH3 
D) C6H5CH(CH3)2 
E) All of these choices.

Question 8

What would be the major product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 9

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

Accepted Answer

A) C6H5CH2CH3 + Cl2,Fe $\to$ 
B) C6H5CH2CH3 + Cl2,400S1U1P1$\circ$S1S1P0C $\to$ 
C) C6H5CH2CH2OH + PCl5 $\to$ 
D) C6H5CH=CH2 + HCl,peroxide $\to$ 
E) C6H6 + CH3CH2Cl,AlCl3 $\to$ 
A) C6H5CH2CH3 + Cl2,Fe $\to$ 
B) C6H5CH2CH3 + Cl2,400S1U1P1$\circ$S1S1P0C $\to$ 
C) C6H5CH2CH2OH + PCl5 $\to$ 
D) C6H5CH=CH2 + HCl,peroxide $\to$ 
E) C6H6 + CH3CH2Cl,AlCl3 $\to$

Question 10

Which compound is capable of undergoing both SN1 and SN2 reactions in ordinary nonacidic solvents?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 11

Which of the following compounds would yield the greatest amount of meta product when subjected to ring nitration?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 12

This molecule does not normally participate as a reactant in a Friedel-Crafts reaction.

Accepted Answer

A) Benzene 
B) Chlorobenzene 
C) Nitrobenzene 
D) Toluene 
E) tert-Butylbenzene 
A) Benzene 
B) Chlorobenzene 
C) Nitrobenzene 
D) Toluene 
E) tert-Butylbenzene

Question 13

Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:

Accepted Answer

A) Friedel-Crafts alkylation 
B) Friedel-Crafts acylation 
C) Nitration 
D) Sulfonation 
E) Chlorination 
A) Friedel-Crafts alkylation 
B) Friedel-Crafts acylation 
C) Nitration 
D) Sulfonation 
E) Chlorination

Question 14

Suggest a reasonable synthetic strategy for the synthesis of 3,5-dinitrobenzyl alcohol from benzaldehyde.

Accepted Answer

The answer of Suggest a reasonable synthetic strategy for the...

Question 15

What product would result from the following series of reactions,

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 16

Based on your knowledge of electrophilic aromatic substitution,and assuming the thiophene ring of benzo[b]thiophene (shown)is activated toward electrophilic aromatic substituted more so than the benzenoid ring,predict the preferential position of attack of an electrophile,i.e.,does the electrophile E+ attack carbon 2,or 3? Explain your answer.   Which substitution product forms preferentially and why?

Accepted Answer

3-substitution is preferred,since this l

Question 17

What would be the product of the following reaction sequence?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 18

Substituent groups affect both ___ and ___ in electrophilic aromatic substitution reactions.

Accepted Answer

reactivity

Question 19

Which reagent(s)would you use to carry out the following transformation? toluene $\to$ benzyl bromide

Accepted Answer

A) Br2,FeBr3 
B) N-Bromosuccinimide,ROOR,h$v$ 
C) HBr 
D) Br2/CCl4 
E) NaBr,H2SO4 
A) Br2,FeBr3 
B) N-Bromosuccinimide,ROOR,h$v$ 
C) HBr 
D) Br2/CCl4 
E) NaBr,H2SO4

Question 20

Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

Accepted Answer

A) Chlorobenzene 
B) Nitrobenzene 
C) Acetophenone 
D) (Trifluoromethyl)benzene 
E) All of these choices could be used. 
A) Chlorobenzene 
B) Nitrobenzene 
C) Acetophenone 
D) (Trifluoromethyl)benzene 
E) All of these choices could be used.

Exam 15: Reactions of Aromatic Compounds

Which would be the major product(s)of the following reaction?

Which is the best sequence of reactions for the following transformation?

What would you expect to be the major product obtained from the following reaction?

What feature is common to all meta-directing groups?

What is a feature found in all ortho-para directing groups?

Propose a reasonable synthesis of the following compound from benzene.

Benzoic acid can be prepared by the oxidation of which of the following compounds:

What would be the major product of the following reaction?

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

Which compound is capable of undergoing both SN1 and SN2 reactions in ordinary nonacidic solvents?

Which of the following compounds would yield the greatest amount of meta product when subjected to ring nitration?

This molecule does not normally participate as a reactant in a Friedel-Crafts reaction.

Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the case of:

Suggest a reasonable synthetic strategy for the synthesis of 3,5-dinitrobenzyl alcohol from benzaldehyde.

What product would result from the following series of reactions,

What would be the product of the following reaction sequence?

Substituent groups affect both ___ and ___ in electrophilic aromatic substitution reactions.

Which reagent(s)would you use to carry out the following transformation? toluene →\to→ benzyl bromide

Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which compound is capable of undergoing both S_N1 and S_N2 reactions in ordinary nonacidic solvents?

Substituent groups affect both _ and _ in electrophilic aromatic substitution reactions.

Which reagent(s)would you use to carry out the following transformation? toluene $\to$ benzyl bromide