Question 1

Name:

Accepted Answer

1-((1S,3R)

Question 2

Draw: o-chlorophenol

Accepted Answer

The answer of Draw: o-chlorophenol...

Question 3

Consider the following compound.Atoms other than carbon and hydrogen are labeled.   Which of the following is not valid?

Accepted Answer

A) naming of the parent compound,benzene. 
B) 1,4-disubstitution is present. 
C) para prefix applicable. 
D) classified as aromatic. 
A) naming of the parent compound,benzene. 
B) 1,4-disubstitution is present. 
C) para prefix applicable. 
D) classified as aromatic.

Question 4

Which of the following aromatic compounds will have largest number of signals in a 13CNMR?

Accepted Answer

A) 1,4-dimethylbenzene (p-methyl toluene) 
B) 1,3,5-trimethylbenzene (mesitylene) 
C) 1,2,4,5-tetramethylbenzene 
D) All produce the same number of signals. 
A) 1,4-dimethylbenzene (p-methyl toluene) 
B) 1,3,5-trimethylbenzene (mesitylene) 
C) 1,2,4,5-tetramethylbenzene 
D) All produce the same number of signals.

Question 5

Exhibit 15-2
Answer the following question(s) concerning sulfathiazole,below.  
-Refer to Exhibit 15-2.Assuming that the sulfur atom is sp2-hybridized,how many π-electrons are there in the sulfathiazole ring?

Accepted Answer

There are six π-elec

Question 6

Draw: 3,5-dimethylbenzoic acid

Accepted Answer

The answer of Draw: 3,5-dimethylbenzoic acid...

Question 7

Exhibit 15-2
Answer the following question(s) concerning sulfathiazole,below.  
-Refer to Exhibit 15-2.What reactivity do you predict for sulfathiazole?

Accepted Answer

Sulfathiazole is predicted to

Question 8

Exhibit 15-2
Answer the following question(s) concerning sulfathiazole,below.  
-Refer to Exhibit 15-2.What is the hybridization of the nitrogen atom in sulfathiazole?

Accepted Answer

The hybridization of

Question 9

How many monosubstituted products would you expect for the bromination of naphthalene?

Accepted Answer

A) 2 
B) 4 
C) 6 
D) 8 
A) 2 
B) 4 
C) 6 
D) 8

Question 10

Exhibit 15-4
Consider the data below to answer the following question(s).  
-Refer to Exhibit 15-4.Conjugate bases QB and ZB are both resonance stabilized.Draw the indicated number of resonance forms for QB and ZB.

Accepted Answer

The answer of Exhibit 15-4
Consider the data below to answer...

Question 11

Exhibit 15-6
Consider the data below to answer the following question(s).
CS1U1B19S1U1B0HS1U1B112S1U1B0;S1U1P11S1S1P0H NMR:
6.65 δ (singlet,3H)
2.25 δ (singlet,9H)
-Refer to Exhibit 15-6.Describe the signal at 2.25 δ in terms of its splitting,integration and chemical shift.

Accepted Answer

The signal at 2.25 δ indicates

Question 12

Draw: p-bromoaniline

Accepted Answer

The answer of Draw: p-bromoaniline...

Question 13

Exhibit 15-5
Consider the data below to answer the following question(s).
CS1U1B19S1U1B0HS1U1B112S1U1B0;S1U1P11S1S1P0H NMR:
7.18 δ (broad singlet,5H)
2.55 δ (triplet,2H)
1.70 δ (sextet,2H)
0.9 δ (triplet,3H)
-Refer to Exhibit 15-5.Describe the signal at 0.9 δ in terms of its splitting,integration and chemical shift.

Accepted Answer

The integration of the signal at 0.9 δ i

Question 14

What is the structure of a hydrocarbon that shows a molecular ion at m/z = 182 in the mass spectrum and has the following 1H NMR spectrum?
7.2 δ,singlet,5H
2.9 δ,singlet,2H

Accepted Answer

The molecular weight of the hydrocarbon

Question 15

Give the IUPAC name for:

Accepted Answer

2-bromotol

Question 16

Name:

Accepted Answer

m-nitrotol

Question 17

What m/z ratio range might be common to many substituted benzene compounds?

Accepted Answer

A) 72 - 77 ppm 
B) 26 - 38 ppm 
C) 81 - 88 ppm 
D) less than 59 ppm 
A) 72 - 77 ppm 
B) 26 - 38 ppm 
C) 81 - 88 ppm 
D) less than 59 ppm

Question 18

Exhibit 15-5
Consider the data below to answer the following question(s).
CS1U1B19S1U1B0HS1U1B112S1U1B0;S1U1P11S1S1P0H NMR:
7.18 δ (broad singlet,5H)
2.55 δ (triplet,2H)
1.70 δ (sextet,2H)
0.9 δ (triplet,3H)
-Refer to Exhibit 15-5.Describe the signal at 1.70 δ in terms of its splitting,integration and chemical shift.

Accepted Answer

The integration of the signal at 1.70 δ

Question 19

Exhibit 15-7
Consider the data below to answer the following question(s).
CS1U1B17S1U1B0HS1U1B17S1U1B0ClO;IR absorption at 810 cm−S1U1P11S1S1P0   Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/
-Refer to Exhibit 15-7.What is the significance of an IR absorption at 810 cm−1?

Accepted Answer

An IR absorption at

Question 20

Exhibit 15-4
Consider the data below to answer the following question(s).  
-Refer to Exhibit 15-4.Which of the compounds above,Q or Z,would you predict to be most acidic? Explain your answer.

Accepted Answer

The conjugate bases of Compounds Q and Z

Exam 15: Benzene and Aromaticity

Name:

Draw: o-chlorophenol

Consider the following compound.Atoms other than carbon and hydrogen are labeled. Which of the following is not valid?

Which of the following aromatic compounds will have largest number of signals in a 13CNMR?

Exhibit 15-2 Answer the following question(s) concerning sulfathiazole,below. -Refer to Exhibit 15-2.Assuming that the sulfur atom is sp2-hybridized,how many π-electrons are there in the sulfathiazole ring?

Draw: 3,5-dimethylbenzoic acid

Exhibit 15-2 Answer the following question(s) concerning sulfathiazole,below. -Refer to Exhibit 15-2.What reactivity do you predict for sulfathiazole?

Exhibit 15-2 Answer the following question(s) concerning sulfathiazole,below. -Refer to Exhibit 15-2.What is the hybridization of the nitrogen atom in sulfathiazole?

How many monosubstituted products would you expect for the bromination of naphthalene?

Exhibit 15-4 Consider the data below to answer the following question(s). -Refer to Exhibit 15-4.Conjugate bases QB and ZB are both resonance stabilized.Draw the indicated number of resonance forms for QB and ZB.

Exhibit 15-6 Consider the data below to answer the following question(s). C9H12;1H NMR: 6.65 δ (singlet,3H) 2.25 δ (singlet,9H) -Refer to Exhibit 15-6.Describe the signal at 2.25 δ in terms of its splitting,integration and chemical shift.

Draw: p-bromoaniline

Exhibit 15-5 Consider the data below to answer the following question(s). C9H12;1H NMR: 7.18 δ (broad singlet,5H) 2.55 δ (triplet,2H) 1.70 δ (sextet,2H) 0.9 δ (triplet,3H) -Refer to Exhibit 15-5.Describe the signal at 0.9 δ in terms of its splitting,integration and chemical shift.

What is the structure of a hydrocarbon that shows a molecular ion at m/z = 182 in the mass spectrum and has the following 1H NMR spectrum? 7.2 δ,singlet,5H 2.9 δ,singlet,2H

Give the IUPAC name for:

Name:

What m/z ratio range might be common to many substituted benzene compounds?

Exhibit 15-5 Consider the data below to answer the following question(s). C9H12;1H NMR: 7.18 δ (broad singlet,5H) 2.55 δ (triplet,2H) 1.70 δ (sextet,2H) 0.9 δ (triplet,3H) -Refer to Exhibit 15-5.Describe the signal at 1.70 δ in terms of its splitting,integration and chemical shift.

Exhibit 15-7 Consider the data below to answer the following question(s). C7H7ClO;IR absorption at 810 cm−1 Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 15-7.What is the significance of an IR absorption at 810 cm−1?

Exhibit 15-4 Consider the data below to answer the following question(s). -Refer to Exhibit 15-4.Which of the compounds above,Q or Z,would you predict to be most acidic? Explain your answer.

Structure and Bonding

Polar Covalent Bonds;acids and Bases

Organic Compounds: Alkanes and Their Stereochemistry

Organic Compounds: Cycloalkanes and Their Stereochemistry

Stereochemistry at Tetrahedral Centers

An Overview of Organic Reactions

Par 1

Alkenes: Structure and Reactivity

Alkenes: Reactions and Synthesis

Alkynes: an Introduction to Organic Synthesis

Organohalides

Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

Par 2

Structure Determination: Mass Spectrometry and Infrared Spectroscopy

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Conjugated Compounds and Ultraviolet Spectroscopy

Par 3

Chemistry of Benzene: Electrophilic Aromatic Substitution

Alcohols and Phenols

Ethers and Epoxides;thiols and Sulfides

Aldehydes and Ketones: Nucleophilic Addition Reactions

Par 4

Carboxylic Acids and Nitriles

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution Reactions

Carbonyl Condensation Reactions

Par 5

Amines and Heterocycles

Biomolecules: Carbohydrates

Biomolecules: Amino Acids,peptides,and Proteins

Par 7

Biomolecules: Lipids

Biomolecules: Nucleic Acids

The Organic Chemistry of Metabolic Pathways

Orbitals and Organic Chemistry: Pericyclic Reactions

Synthetic Polymers

Par 1

Filters

Which of the following aromatic compounds will have largest number of signals in a ¹³CNMR?

Exhibit 15-2 Answer the following question(s) concerning sulfathiazole,below. -Refer to Exhibit 15-2.Assuming that the sulfur atom is sp²-hybridized,how many π-electrons are there in the sulfathiazole ring?

Exhibit 15-6 Consider the data below to answer the following question(s). C₉H₁₂;¹H NMR: 6.65 δ (singlet,3H) 2.25 δ (singlet,9H) -Refer to Exhibit 15-6.Describe the signal at 2.25 δ in terms of its splitting,integration and chemical shift.

Exhibit 15-5 Consider the data below to answer the following question(s). C₉H₁₂;¹H NMR: 7.18 δ (broad singlet,5H) 2.55 δ (triplet,2H) 1.70 δ (sextet,2H) 0.9 δ (triplet,3H) -Refer to Exhibit 15-5.Describe the signal at 0.9 δ in terms of its splitting,integration and chemical shift.

What is the structure of a hydrocarbon that shows a molecular ion at m/z = 182 in the mass spectrum and has the following ¹H NMR spectrum? 7.2 δ,singlet,5H 2.9 δ,singlet,2H

Exhibit 15-5 Consider the data below to answer the following question(s). C₉H₁₂;¹H NMR: 7.18 δ (broad singlet,5H) 2.55 δ (triplet,2H) 1.70 δ (sextet,2H) 0.9 δ (triplet,3H) -Refer to Exhibit 15-5.Describe the signal at 1.70 δ in terms of its splitting,integration and chemical shift.

Exhibit 15-7 Consider the data below to answer the following question(s). C₇H₇ClO;IR absorption at 810 cm−¹ Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ -Refer to Exhibit 15-7.What is the significance of an IR absorption at 810 cm−¹?