Question 1

Suggest a stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1-bromobutane.

Accepted Answer

The answer of Suggest a stepwise synthesis for 5-methyl-2-hexanone from...

Question 2

Predict the product for 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 3

The 1H NMR spectrum of a compound with formula C7H14O shows only two signals. Which one of the following is a possible structure for this compound?

Accepted Answer

A)  2-heptanone 
B)  3-heptanone 
C)  2,4-dimethyl-3-pentanone 
D)  2,2-dimethyl-3-pentanone 
E)  Two of the above 
A)  2-heptanone 
B)  3-heptanone 
C)  2,4-dimethyl-3-pentanone 
D)  2,2-dimethyl-3-pentanone 
E)  Two of the above

Question 4

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. HOCH₂CH₂O

Question 5

Provide the product of the following reaction.

Accepted Answer

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

Question 6

Predict the product(s) for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these

Question 7

The 1H NMR spectrum of a compound with formula C7H14O shows a singlet at 9.2 ppm. Which one of the following is a possible structure for this compound?

Accepted Answer

A)  2-methyl-3-hexanone 
B)  2-methylhexanal 
C)  2,2 -dimethylpentanal 
D)  2,2-dimethyl-3-pentanone 
E)  B & C 
A)  2-methyl-3-hexanone 
B)  2-methylhexanal 
C)  2,2 -dimethylpentanal 
D)  2,2-dimethyl-3-pentanone 
E)  B & C

Question 8

Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4 followed by water?

Accepted Answer

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

Question 9

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  1. H2O/ H2SO4,
2) PCC/CH2Cl2 
B)  PCC/ CH2Cl2 
C)  1. 9-BBN,
2) H2O2/NaOH/H2O 
D)  1. O3,
2) Zn/acetic acid 
E)  1. 9-BBN
2) H2O2/NaOH/H2O
3) CrO3/H2SO4/H2O 
A)  1. H2O/ H2SO4,
2) PCC/CH2Cl2 
B)  PCC/ CH2Cl2 
C)  1. 9-BBN,
2) H2O2/NaOH/H2O 
D)  1. O3,
2) Zn/acetic acid 
E)  1. 9-BBN
2) H2O2/NaOH/H2O
3) CrO3/H2SO4/H2O

Question 10

Provide the reactant(s) necessary to prepare the following compound.

Accepted Answer

The answer of Provide the reactant(s) necessary to prepare the...

Question 11

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 12

Which of the following compounds can be classified as an acetal?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these

Question 13

Provide the reactant for the following reaction.

Accepted Answer

A)  cyclohexanone 
B)  cyclohexanecarbaldehyde 
C)  cyclohexylpropanone 
D)  3-cyclohexylpropanal 
A)  cyclohexanone 
B)  cyclohexanecarbaldehyde 
C)  cyclohexylpropanone 
D)  3-cyclohexylpropanal

Question 14

Provide the structure of the product, when cyclohexanecarbaldehyde reacts with excess 2-propanol in the presence of sulfuric acid.

Accepted Answer

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

Question 15

Predict the product for 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 16

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  NaBH4/CH3OH 
B)  1. NH2NH2/H+ 2. KOH/H2O/heat 
C)  H2/Ni 
D)  1. LiAlH4 , 2. H2O 
A)  NaBH4/CH3OH 
B)  1. NH2NH2/H+ 2. KOH/H2O/heat 
C)  H2/Ni 
D)  1. LiAlH4 , 2. H2O

Question 17

Provide the product for 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

Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.

Accepted Answer

Steric effect: the carbonyl group of the

Question 19

Provide the structure of the ylide needed to prepare 3-ethyl-3-heptene from 3-pentanone using a Wittig reaction.

Accepted Answer

A)  Ph3P=CH(CH2CH3)2 
B)  Ph3P=CHCH2CH3 
C)  Ph3P=CHCH2CH2CH3 
D)  Ph3P=CH2 
E)  Ph3P=CHCH2(CH3)2 
A)  Ph3P=CH(CH2CH3)2 
B)  Ph3P=CHCH2CH3 
C)  Ph3P=CHCH2CH2CH3 
D)  Ph3P=CH2 
E)  Ph3P=CHCH2(CH3)2

Question 20

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Exam 19: Aldehydes and Ketones

Suggest a stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1-bromobutane.

Predict the product for the following reaction.

The 1H NMR spectrum of a compound with formula C7H14O shows only two signals. Which one of the following is a possible structure for this compound?

Provide the reagents necessary to carry out the following conversion.

Provide the product of the following reaction.

Predict the product(s) for the following reaction.

The 1H NMR spectrum of a compound with formula C7H14O shows a singlet at 9.2 ppm. Which one of the following is a possible structure for this compound?

Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4 followed by water?

Provide the reagents necessary to carry out the following conversion.

Provide the reactant(s) necessary to prepare the following compound.

Predict the product for the following reaction.

Which of the following compounds can be classified as an acetal?

Provide the reactant for the following reaction.

Provide the structure of the product, when cyclohexanecarbaldehyde reacts with excess 2-propanol in the presence of sulfuric acid.

Predict the product for the following reaction.

Provide the reagents necessary to carry out the following conversion.

Provide the product for the following reaction sequence.

Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.

Provide the structure of the ylide needed to prepare 3-ethyl-3-heptene from 3-pentanone using a Wittig reaction.

Predict the product for the following reaction.

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

The ¹H NMR spectrum of a compound with formula C₇H₁₄O shows only two signals. Which one of the following is a possible structure for this compound?

The ¹H NMR spectrum of a compound with formula C₇H₁₄O shows a singlet at 9.2 ppm. Which one of the following is a possible structure for this compound?

Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH₄followed by water?