Question 1

The relative reactivity of acyl compounds toward nucleophilic acyl addition-elimination is:

Accepted Answer

A)  Amide > ester > acid anhydride > acyl chloride 
B)  Acyl chloride > ester > acid anhydride > amide 
C)  Ester > acyl chloride > acid anhydride > amide 
D)  Acyl chloride > acid anhydride > ester > amide 
E)  Acid anhydride > acyl chloride > ester > amide 
A)  Amide > ester > acid anhydride > acyl chloride 
B)  Acyl chloride > ester > acid anhydride > amide 
C)  Ester > acyl chloride > acid anhydride > amide 
D)  Acyl chloride > acid anhydride > ester > amide 
E)  Acid anhydride > acyl chloride > ester > amide

Question 2

Which reactant is unlikely to produce the indicated product upon strong heating?

Accepted Answer

A)  2,2-Dimethylpropanedioic acid $\rightarrow$2-methylpropanoic acid 
B)  2-Ethylpropanedioic acid $\rightarrow$Butanoic acid 
C)  2-Methyl-3-oxo-pentanoic acid $\rightarrow$3-Pentanone 
D)  2-Methyl-4-oxo-pentanoic acid $\rightarrow$ 2-Methyl-3-butanone 
E)  4-Methyl-3-oxo-heptanoic acid $\rightarrow$3-Methyl-2-hexanone 
A)  2,2-Dimethylpropanedioic acid $\rightarrow$2-methylpropanoic acid 
B)  2-Ethylpropanedioic acid $\rightarrow$Butanoic acid 
C)  2-Methyl-3-oxo-pentanoic acid $\rightarrow$3-Pentanone 
D)  2-Methyl-4-oxo-pentanoic acid $\rightarrow$ 2-Methyl-3-butanone 
E)  4-Methyl-3-oxo-heptanoic acid $\rightarrow$3-Methyl-2-hexanone

Question 3

In which of the following sequences are the compounds listed in order of decreasing acidity?

Accepted Answer

A)  PhCOOH > H2O > PhOH > PhCH2OH > PhH 
B)  PhCOOH > PhOH > H2O > PhCH2OH > PhH 
C)  PhH > H2O > PhOH > PhCH2OH > PhCOOH 
D)  PhOH > H2O > PhCOOH > PhCH2OH > PhH 
E)  PhCOOH > H2O > PhOH > PhH > PhCH2OH 
A)  PhCOOH > H2O > PhOH > PhCH2OH > PhH 
B)  PhCOOH > PhOH > H2O > PhCH2OH > PhH 
C)  PhH > H2O > PhOH > PhCH2OH > PhCOOH 
D)  PhOH > H2O > PhCOOH > PhCH2OH > PhH 
E)  PhCOOH > H2O > PhOH > PhH > PhCH2OH

Question 4

Which of the following would serve as a reasonable synthesis of ethyl benzoate?

Accepted Answer

A) 
  
B) 
  
C) 
  
D)  All of the above 
E)  None of the above 
A) 
  
B) 
  
C) 
  
D)  All of the above 
E)  None of the above

Question 5

A compound with the molecular formula C5H10O2 gave the following 1H NMR spectrum: triplet,
 $\delta$  0.90
Multiplet,
 $\delta$ 1.60
Singlet,
 $\delta$  1.95
Triplet,
 $\delta$  3.95
The IR spectrum showed a strong absorption band near 1740 cm-1.The most likely structure for the compound is:

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E) 
  
A) 
  
B) 
  
C) 
  
D) 
  
E)

Question 6

The product of the following reaction is:

Accepted Answer

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

Question 7

What is the expected product,A,of the following reaction sequence?

Accepted Answer

A)  HCO2CH2C6H5 
B)  C6H5CH2COOH 
C)  C6H5CH2OSO3H 
D)  C6H5CHClCOOH 
E)  O=C(CH2C6H5)2 
A)  HCO2CH2C6H5 
B)  C6H5CH2COOH 
C)  C6H5CH2OSO3H 
D)  C6H5CHClCOOH 
E)  O=C(CH2C6H5)2

Question 8

In which of the following are the compounds listed in order of decreasing acidity?

Accepted Answer

A)  CH3CO2H > CH3CH2OH > C6H5OH > H2O 
B)  C6H5OH > CH3CO2H > H2O > CH3CH2OH 
C)  CH3CO2H > H2O > C6H5OH > CH3CH2OH 
D)  H2O > CH3CO2H > C6H5OH > CH3CH2OH 
E)  None of the above 
A)  CH3CO2H > CH3CH2OH > C6H5OH > H2O 
B)  C6H5OH > CH3CO2H > H2O > CH3CH2OH 
C)  CH3CO2H > H2O > C6H5OH > CH3CH2OH 
D)  H2O > CH3CO2H > C6H5OH > CH3CH2OH 
E)  None of the above

Question 9

Litmus paper turns ___________ when an aqueous solution of a carboxylic acid is dropped on it.

Accepted Answer

The answer of Litmus paper turns ___________ when an aqueous...

Question 10

What is the expected product,A,of the following reaction sequence?

Accepted Answer

A)  HCO2CH2C6H5 
B)  C6H5CH2COOH 
C)  C6H5CH2OSO3H 
D)  C6H5CHClCOOH 
E)  O=C(CH2C6H5)2 
A)  HCO2CH2C6H5 
B)  C6H5CH2COOH 
C)  C6H5CH2OSO3H 
D)  C6H5CHClCOOH 
E)  O=C(CH2C6H5)2

Question 11

A nitrile is prepared from the corresponding primary amide by reaction with which of these?

Accepted Answer

A)  HCl 
B)  Cl2 
C)  P4O10 
D)  HOCl 
E)  AlCl3 
A)  HCl 
B)  Cl2 
C)  P4O10 
D)  HOCl 
E)  AlCl3

Question 12

In which of the following sequences are the compounds listed in order of decreasing acidity?

Accepted Answer

A)  CH3COOH > H2O > CH3CH2OH > HC$ \equiv$CH > NH3 
B)  CH3CH2OH > CH3COOH > H2O > HC$ \equiv$CH > NH3 
C)  CH3COOH > CH3CH2OH > H2O > NH3 > HC$ \equiv$CH 
D)  H2O > CH3COOH > CH3CH2OH > HC$ \equiv$CH > NH3 
E)  CH3CH2OH > H2O > CH3COOH > HC$ \equiv$CH > NH3 
A)  CH3COOH > H2O > CH3CH2OH > HC$ \equiv$CH > NH3 
B)  CH3CH2OH > CH3COOH > H2O > HC$ \equiv$CH > NH3 
C)  CH3COOH > CH3CH2OH > H2O > NH3 > HC$ \equiv$CH 
D)  H2O > CH3COOH > CH3CH2OH > HC$ \equiv$CH > NH3 
E)  CH3CH2OH > H2O > CH3COOH > HC$ \equiv$CH > NH3

Question 13

$\gamma$- And $\delta$-hydroxy acids can be esterified intramolecularly to form compounds known as which of these?

Accepted Answer

A)  Anhydrides 
B)  Cycloalkenes 
C)  Lactones 
D)  Lactams 
E)  Cyclic ketones 
A)  Anhydrides 
B)  Cycloalkenes 
C)  Lactones 
D)  Lactams 
E)  Cyclic ketones

Question 14

The linkages that join amino acids together to form proteins are primarily ___________ bonds.

Accepted Answer

The answer of The linkages that join amino acids together...

Question 15

A compound has the molecular formula,C6H12O2.Its IR spectrum shows a strong absorption band near 1740 cm-1;its 1H NMR spectrum consists of two singlets,at  $\delta$1.2 and  $\delta$3.6.The most likely structure for this compound is:

Accepted Answer

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

Question 16

Which reagent would serve as the basis for a simple chemical test to distinguish between benzoic acid and benzamide?

Accepted Answer

A)  Cold dilute NaOH 
B)  Cold dilute NaHCO3 
C)  Cold concd H2SO4 
D)  More than one of these 
E)  None of these 
A)  Cold dilute NaOH 
B)  Cold dilute NaHCO3 
C)  Cold concd H2SO4 
D)  More than one of these 
E)  None of these

Question 17

Which of the following statements concerning nitriles is incorrect?

Accepted Answer

A)  Nitriles can be hydrolyzed to carboxylic acids. 
B)  Nitriles can be formed from (many)alkyl halides by nucleophilic substitution by cyanide ion. 
C)  Nitriles can be reduced with excess lithium aluminum hydride to primary amines,RNH2. 
D)  Nitriles react with Grignard reagents to form tertiary alcohols. 
E)  Nitriles can be made by the dehydration of amides. 
A)  Nitriles can be hydrolyzed to carboxylic acids. 
B)  Nitriles can be formed from (many)alkyl halides by nucleophilic substitution by cyanide ion. 
C)  Nitriles can be reduced with excess lithium aluminum hydride to primary amines,RNH2. 
D)  Nitriles react with Grignard reagents to form tertiary alcohols. 
E)  Nitriles can be made by the dehydration of amides.

Question 18

Draw the structure for 3-methylbutanoic anhydride.

Accepted Answer

The answer of Draw the structure for 3-methylbutanoic anhydride....

Question 19

A compound has the formula C7H14O2.The 13C and 1H NMR spectral data for this
compound are:
13C NMR
Broadband decoupled 13C NMR: 22.2,27.7,32.2,33.8,51.4,174.4 δ
DEPT-90: 27.7 δ
DEPT-135: positive peaks at 22.2,27.7,51.4 δ;negative peaks at 32.2,33.8 δ
1H NMR
0.90 δ,doublet (6H)
1.55 δ,multiplet (3H)
2.30 δ,triplet (2H)
3.67 δ,singlet (3H)
Suggest a structure consistent with this data.

Accepted Answer

Question 20

Complete the following reaction sequence,giving details of all significant intermediates.

Accepted Answer

The answer of Complete the following reaction sequence,giving details of...

Exam 17: Aldehydes and Ketones Ii Aldol Reactions

The relative reactivity of acyl compounds toward nucleophilic acyl addition-elimination is:

Which reactant is unlikely to produce the indicated product upon strong heating?

In which of the following sequences are the compounds listed in order of decreasing acidity?

Which of the following would serve as a reasonable synthesis of ethyl benzoate?

A compound with the molecular formula C5H10O2 gave the following 1H NMR spectrum: triplet, δ\deltaδ 0.90 Multiplet, δ\deltaδ 1.60 Singlet, δ\deltaδ 1.95 Triplet, δ\deltaδ 3.95 The IR spectrum showed a strong absorption band near 1740 cm-1.The most likely structure for the compound is:

The product of the following reaction is:

What is the expected product,A,of the following reaction sequence?

In which of the following are the compounds listed in order of decreasing acidity?

Litmus paper turns ___________ when an aqueous solution of a carboxylic acid is dropped on it.

What is the expected product,A,of the following reaction sequence?

A nitrile is prepared from the corresponding primary amide by reaction with which of these?

In which of the following sequences are the compounds listed in order of decreasing acidity?

γ\gammaγ - And δ\deltaδ -hydroxy acids can be esterified intramolecularly to form compounds known as which of these?

The linkages that join amino acids together to form proteins are primarily ___________ bonds.

A compound has the molecular formula,C6H12O2.Its IR spectrum shows a strong absorption band near 1740 cm-1;its 1H NMR spectrum consists of two singlets,at δ\deltaδ 1.2 and δ\deltaδ 3.6.The most likely structure for this compound is:

Which reagent would serve as the basis for a simple chemical test to distinguish between benzoic acid and benzamide?

Which of the following statements concerning nitriles is incorrect?

Draw the structure for 3-methylbutanoic anhydride.

Complete the following reaction sequence,giving details of all significant intermediates.

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

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

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

A compound with the molecular formula C₅H₁₀O₂ gave the following ¹H NMR spectrum: triplet, $\delta$ 0.90 Multiplet, $\delta$ 1.60 Singlet, $\delta$ 1.95 Triplet, $\delta$ 3.95 The IR spectrum showed a strong absorption band near 1740 cm^-1.The most likely structure for the compound is:

$\gamma$ - And $\delta$ -hydroxy acids can be esterified intramolecularly to form compounds known as which of these?