Question 1

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 2

Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1728 cm−1
Broadband decoupled 13C NMR: 22.59,23.57,52.66,202.71  $\delta$
DEPT Experiments show: signal at 23.57  $\delta$ as CH,signal at 22.59  $\delta$as CH3,and signal at 52.66  $\delta$ as CH2.

Accepted Answer

The answer of Propose a structure that fits the following...

Question 3

What,in general,is the order of increasing reactivity of these carbonyl compounds towards nucleophilic reagents?

Accepted Answer

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

Question 4

What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?

Accepted Answer

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

Question 5

Which of the following is formed when 3-methylcyclopentanone reacts with hydroxylamine?

Accepted Answer

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

Question 6

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

Accepted Answer

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

Question 7

What is the correct structure for (S)-5-bromo-2-heptanone?

Accepted Answer

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

Question 8

Explain clearly how you might use 1H NMR to distinguish between
2-phenylacetaldehyde and acetophenone.

Accepted Answer

A quick inspection of ¹H NMR

Question 9

Which of the following is not a synthesis of benzophenone,

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above will give benzophenone. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above will give benzophenone.

Question 10

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 11

Select the structure of the major product in 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 12

What is the major 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 13

Acetals are unstable in the presence of an aqueous solution of which of these?

Accepted Answer

A)  HCl 
B)  NaOH 
C)  KHCO3 
D)  Na2CO3 
E)  NaCl 
A)  HCl 
B)  NaOH 
C)  KHCO3 
D)  Na2CO3 
E)  NaCl

Question 14

What is the correct structure for 4-chloro-3-methylbenzaldehyde?

Accepted Answer

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

Question 15

A correct name for the following compound would be which of those below?

Accepted Answer

A)  2,5-Dimethyl-6-hexanal 
B)  2,5-Dimethylhexanal 
C)  2-Aldehydoisohexane 
D)  3,5-Dimethylheptanone 
E)  1-Hydro-2,5-dimethyl-1-hexanone 
A)  2,5-Dimethyl-6-hexanal 
B)  2,5-Dimethylhexanal 
C)  2-Aldehydoisohexane 
D)  3,5-Dimethylheptanone 
E)  1-Hydro-2,5-dimethyl-1-hexanone

Question 16

The driving force for the Wittig reaction is the formation of the very strong _______________ bond in _______________.

Accepted Answer

P-O bond;t

Question 17

A compound with an OH and OR group attached to the same carbon is known as a(n)_____________.

Accepted Answer

The answer of A compound with an OH and OR...

Question 18

What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?

Accepted Answer

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

Question 19

Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with hydroxylamine?

Accepted Answer

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

Question 20

Which is the IUPAC name for the structure shown below?

Accepted Answer

A)  (R)-5-Bromo-2-heptanal 
B)  (S)-5-Bromo-2-heptanal 
C)  (R)-5-Bromo-2-heptanone 
D)  (S)-5-Bromo-2-heptanone 
E)  (R)-3-Bromopentyl methyl ketone 
A)  (R)-5-Bromo-2-heptanal 
B)  (S)-5-Bromo-2-heptanal 
C)  (R)-5-Bromo-2-heptanone 
D)  (S)-5-Bromo-2-heptanone 
E)  (R)-3-Bromopentyl methyl ketone

Exam 16: Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

What would be the product of the following reaction sequence?

Propose a structure that fits the following spectroscopic data: C5H10O IR: 1728 cm−1 Broadband decoupled 13C NMR: 22.59,23.57,52.66,202.71 δ\deltaδ DEPT Experiments show: signal at 23.57 δ\deltaδ as CH,signal at 22.59 δ\deltaδ as CH3,and signal at 52.66 δ\deltaδ as CH2.

What,in general,is the order of increasing reactivity of these carbonyl compounds towards nucleophilic reagents?

What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?

Which of the following is formed when 3-methylcyclopentanone reacts with hydroxylamine?

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

What is the correct structure for (S)-5-bromo-2-heptanone?

Explain clearly how you might use 1H NMR to distinguish between 2-phenylacetaldehyde and acetophenone.

Which of the following is not a synthesis of benzophenone,

What would be the product of the following reaction sequence?

Select the structure of the major product in the following reaction.

What is the major product of the following reaction sequence?

Acetals are unstable in the presence of an aqueous solution of which of these?

What is the correct structure for 4-chloro-3-methylbenzaldehyde?

A correct name for the following compound would be which of those below?

The driving force for the Wittig reaction is the formation of the very strong _______________ bond in _______________.

A compound with an OH and OR group attached to the same carbon is known as a(n)_____________.

What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?

Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with hydroxylamine?

Which is the IUPAC name for the structure shown below?

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 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

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Propose a structure that fits the following spectroscopic data: C₅H₁₀O IR: 1728 cm⁻¹ Broadband decoupled ¹³C NMR: 22.59,23.57,52.66,202.71 $\delta$ DEPT Experiments show: signal at 23.57 $\delta$ as CH,signal at 22.59 $\delta$ as CH₃,and signal at 52.66 $\delta$ as CH₂.

Explain clearly how you might use ¹H NMR to distinguish between 2-phenylacetaldehyde and acetophenone.

The driving force for the Wittig reaction is the formation of the very strong _ bond in _.