Question 1

Which of the following would be the strongest acid?

Accepted Answer

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

Question 2

What is the product of the following synthesis?

Accepted Answer

A)  2,3-Dibromophenol 
B)  2,4-Dibromophenol 
C)  2,6-Dibromophenol 
D)  2-Hydroxy-3,5-dibromobenzenesulfonic acid 
E)  2,4,6-Tribromophenol 
A)  2,3-Dibromophenol 
B)  2,4-Dibromophenol 
C)  2,6-Dibromophenol 
D)  2-Hydroxy-3,5-dibromobenzenesulfonic acid 
E)  2,4,6-Tribromophenol A

Question 3

When phenol is nitrated with dilute nitric acid,a mixture of o- and p- substituted products is obtained.These products can then be separated by the technique of steam distillation.However,analogous products from the nitration of methoxybenzene cannot be similarly separated by steam distillation.Explain.

Accepted Answer

In order for efficient separation of substances (from a mixture)by steam distillation,there must be relatively large differences in volatility.The more volatile substance passes over with the steam,leaving the less volatile substance in the distillation flask.
Differences in the volatility of the o- and p- nitrophenols may be predicted by considering hydrogen bonding effects: o-nitrophenol can exhibit intramolecular hydrogen bonding,while p-nitrophenol can exhibit intermolecular hydrogen bonding.Consequently,o-nitrophenol is likely to be significantly more volatile than p-nitrophenol,leading to the possibility of efficient separation by steam distillation.
By contrast,since no hydrogen bonding is possible in the products obtained by nitration of methoxybenzene,there is no predictable difference in volatility.Hence,these products cannot be separated by steam distillation.

Question 4

Propose three synthetic methods to outline the steps that could be used (showing all
reagents and reaction conditions)to carry out the transformation shown below.

Accepted Answer

The answer of Propose three synthetic methods to outline the...

Question 5

The cumene hydroperoxide synthesis of phenol is industrially very satisfying,because it takes two inexpensive starting materials,___________ and ___________,and converts them into two valuable products,phenol and __________.

Accepted Answer

benzene;pr

Question 6

Outline the steps involved in the synthesis of 3-bromo-4-methylphenol from 4-nitrotoluene

Accepted Answer

i.Br₂,FeBr₃ ;ii)Fe,HCl

Question 7

Thymol,isolated from thyme,has the following structure:   Which of the following types of signal is NOT expected to be observed in its NMR spectrum?

Accepted Answer

A)  singlet 
B)  doublet 
C)  triplet 
D)  septet 
E)  all of the above types of signals are expected to be observed 
A)  singlet 
B)  doublet 
C)  triplet 
D)  septet 
E)  all of the above types of signals are expected to be observed

Question 8

Draw the structure of the final product obtained when 4-cyclopentylphenol is subjected to the following reaction sequence:
i)NaOH;ii)CH3I;iii)NBS;iv)CH3ONa/CH3OH,heat

Accepted Answer

The answer of Draw the structure of the final product...

Question 9

Give the IUPAC name of the following substance:

Accepted Answer

(R)-methyl

Question 10

Explain why cleavage of phenyl alkyl ether with HBr always give phenol and alkyl bromide.

Accepted Answer

The answer of Explain why cleavage of phenyl alkyl ether...

Question 11

Which of these resonance structures makes the greatest contribution to the hybrid for the intermediate in the SNAr reaction of o-chloronitrobenzene with methoxide ion?

Accepted Answer

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

Question 12

What is the effect of electron releasing and withdrawing group on ring acidity?

Accepted Answer

Electron releasing group on ph

Question 13

What is the final product?

Accepted Answer

A)  1-tert-Butyl-4-ethoxybenzene 
B)  1-tert-Butyl-4-ethylbenzene 
C)  1-tert-Butoxy-4-ethoxybenzene 
D)  tert-Butyl ethyl ether 
E)  1-tert-Butoxy-3-ethylbenzene 
A)  1-tert-Butyl-4-ethoxybenzene 
B)  1-tert-Butyl-4-ethylbenzene 
C)  1-tert-Butoxy-4-ethoxybenzene 
D)  tert-Butyl ethyl ether 
E)  1-tert-Butoxy-3-ethylbenzene

Question 14

What is the product of the reaction of 1 mol of p-benzoquinone with 1 mol of isoprene (2-methyl-1,3-butadiene)?

Accepted Answer

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

Question 15

Which position is predicted to be the chief site of substitution when the following substance reacts with bromine in carbon disulfide at 10$\degree$C ?

Accepted Answer

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

Question 16

Suggest a simple chemical test to distinguish between 4-methylphenol and 2,4,6-trinitrophenol,briefly explaining your rationale.

Accepted Answer

Both substances will dissolve in aq NaOH

Question 17

Which of the following would be most likely to undergo a nucleophilic substitution reaction with aqueous sodium hydroxide by an addition-elimination mechanism?

Accepted Answer

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

Question 18

Draw the structure of the ionic species obtained when the following substance is treated with NaOH:

Accepted Answer

The answer of Draw the structure of the ionic species...

Question 19

Compound L has the molecular formula C11H16O.L is insoluble in water but dissolves in aqueous NaOH.The infrared spectrum of L shows a broad absorption band in the 3200-3600 cm-1 region;its 1H NMR spectrum consists of: triplet, δ 0.80 (3H)
Singlet, δ1.2 (6H)
Quartet,δ 1.5 (2H)
Singlet, δ4.5 (1H)
Multiplet,δ 7.0 (4H)
The most likely structure for compound L is:

Accepted Answer

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

Question 20

Draw the structure of the final product obtained when 3-methylphenol is subjected to the following reaction sequence:
i)NaOH;ii)CH3CH2CH2OSO2OCF3

Accepted Answer

Exam 21: Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Which of the following would be the strongest acid?

What is the product of the following synthesis?

Propose three synthetic methods to outline the steps that could be used (showing all reagents and reaction conditions)to carry out the transformation shown below.

The cumene hydroperoxide synthesis of phenol is industrially very satisfying,because it takes two inexpensive starting materials,___________ and ___________,and converts them into two valuable products,phenol and __________.

Outline the steps involved in the synthesis of 3-bromo-4-methylphenol from 4-nitrotoluene

Thymol,isolated from thyme,has the following structure: Which of the following types of signal is NOT expected to be observed in its NMR spectrum?

Draw the structure of the final product obtained when 4-cyclopentylphenol is subjected to the following reaction sequence: i)NaOH;ii)CH3I;iii)NBS;iv)CH3ONa/CH3OH,heat

Give the IUPAC name of the following substance:

Explain why cleavage of phenyl alkyl ether with HBr always give phenol and alkyl bromide.

Which of these resonance structures makes the greatest contribution to the hybrid for the intermediate in the SNAr reaction of o-chloronitrobenzene with methoxide ion?

What is the effect of electron releasing and withdrawing group on ring acidity?

What is the final product?

What is the product of the reaction of 1 mol of p-benzoquinone with 1 mol of isoprene (2-methyl-1,3-butadiene)?

Which position is predicted to be the chief site of substitution when the following substance reacts with bromine in carbon disulfide at 10 °\degree° C ?

Suggest a simple chemical test to distinguish between 4-methylphenol and 2,4,6-trinitrophenol,briefly explaining your rationale.

Which of the following would be most likely to undergo a nucleophilic substitution reaction with aqueous sodium hydroxide by an addition-elimination mechanism?

Draw the structure of the ionic species obtained when the following substance is treated with NaOH:

Draw the structure of the final product obtained when 3-methylphenol is subjected to the following reaction sequence: i)NaOH;ii)CH3CH2CH2OSO2OCF3

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

The cumene hydroperoxide synthesis of phenol is industrially very satisfying,because it takes two inexpensive starting materials,_____ and _,and converts them into two valuable products,phenol and ______.

Which of these resonance structures makes the greatest contribution to the hybrid for the intermediate in the S_NAr reaction of o-chloronitrobenzene with methoxide ion?

Draw the structure of the final product obtained when 3-methylphenol is subjected to the following reaction sequence: i)NaOH;ii)CH₃CH₂CH₂OSO₂OCF₃