Question 1

Draw structures which show the hydrogen bonding interaction that exists between water and dimethyl ether.

Accepted Answer

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Question 2

Provide the major organic product in the reaction below.
CH3CH2CH2OH   
→

Accepted Answer

Question 3

Predict the products of the following reaction and give a reasonable mechanism for their formation.

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Question 4

Provide the major organic product in the reaction below.

Accepted Answer

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Question 5

Identify all of the following reagents that could be used to accomplish the following transformation.
(More than one answer is possible.)

Accepted Answer

A)  mCPBA 
B)  DMD 
C)  cold KMnO4 
D)  1) Br2 / H2O, 2) NaH 
A)  mCPBA 
B)  DMD 
C)  cold KMnO4 
D)  1) Br2 / H2O, 2) NaH

Question 6

Provide the major organic product in the reaction below.

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Question 7

Provide the major organic product of the reaction shown below.

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Question 8

When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results?

Accepted Answer

A)  3-ethoxypentane 
B)  1-methoxypentane 
C)  1-ethoxypentane 
D)  2-ethoxypentane 
E)  2-methoxypentane 
A)  3-ethoxypentane 
B)  1-methoxypentane 
C)  1-ethoxypentane 
D)  2-ethoxypentane 
E)  2-methoxypentane

Question 9

Provide a structural representation of 3-ethylfuran.

Accepted Answer

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Question 10

Show the reagents necessary to prepare 1,2-epoxy-1-methylcyclopentane from cyclopentanone.

Accepted Answer

1) CH₃MgBr

Question 11

Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr through essentially a(n) ________ mechanism.

Accepted Answer

A)  SN2 
B)  SN1 
C)  E2 
D)  E1 
E)  ring opening 
A)  SN2 
B)  SN1 
C)  E2 
D)  E1 
E)  ring opening

Question 12

Predict the major organic product of the following reaction.

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Question 13

Provide a structure for the expected product of the following reaction.

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Question 14

Which of the following is produced by the reaction of (CH3CH2)2S with CH3CH2I?

Accepted Answer

A)  CH3CH2CH2CH2I 
B)  (CH3CH2)3S+ I- 
C)  (CH3CH2)3S 
D)  CH3SCH2CH2CH3 
E)  CH3CH2SCH2CH2I 
A)  CH3CH2CH2CH2I 
B)  (CH3CH2)3S+ I- 
C)  (CH3CH2)3S 
D)  CH3SCH2CH2CH3 
E)  CH3CH2SCH2CH2I

Question 15

What results when cyclopentene oxide is treated with aqueous base?

Accepted Answer

A)  a racemic mixture of trans-1,2-diols 
B)  a meso trans-1,2-diol 
C)  a racemic mixture of cis-1,2-diols 
D)  a meso cis-1,2-diol 
E)  cyclopentene 
A)  a racemic mixture of trans-1,2-diols 
B)  a meso trans-1,2-diol 
C)  a racemic mixture of cis-1,2-diols 
D)  a meso cis-1,2-diol 
E)  cyclopentene

Question 16

Which of the following reactions is classified as a Williamson ether synthesis?

Accepted Answer

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

Question 17

Which of the following corresponds to the COC bond angle in dimethyl ether?

Accepted Answer

A)  60° 
B)  94° 
C)  110° 
D)  122° 
E)  180° 
A)  60° 
B)  94° 
C)  110° 
D)  122° 
E)  180°

Question 18

Show the best method for preparing 4-propoxytoluene via the Williamson ether synthesis.

Accepted Answer

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Question 19

Propose a structure for the ether of formula C4H10O with the following 1H NMR signals:
δ 1.13 (doublet, 6H), 3.30 (singlet, 3H), 3.65 (septet, 1H) (ppm).

Accepted Answer

Question 20

What reagents are necessary for the following transformation?

Accepted Answer

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Exam 14: Ethers, Epoxides, and Thioethers

Draw structures which show the hydrogen bonding interaction that exists between water and dimethyl ether.

Provide the major organic product in the reaction below. CH3CH2CH2OH →

Predict the products of the following reaction and give a reasonable mechanism for their formation.

Provide the major organic product in the reaction below.

Identify all of the following reagents that could be used to accomplish the following transformation. (More than one answer is possible.)

Provide the major organic product in the reaction below.

Provide the major organic product of the reaction shown below.

When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results?

Provide a structural representation of 3-ethylfuran.

Show the reagents necessary to prepare 1,2-epoxy-1-methylcyclopentane from cyclopentanone.

Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr through essentially a(n) ________ mechanism.

Predict the major organic product of the following reaction.

Provide a structure for the expected product of the following reaction.

Which of the following is produced by the reaction of (CH3CH2)2S with CH3CH2I?

What results when cyclopentene oxide is treated with aqueous base?

Which of the following reactions is classified as a Williamson ether synthesis?

Which of the following corresponds to the COC bond angle in dimethyl ether?

Show the best method for preparing 4-propoxytoluene via the Williamson ether synthesis.

Propose a structure for the ether of formula C4H10O with the following 1H NMR signals: δ 1.13 (doublet, 6H), 3.30 (singlet, 3H), 3.65 (septet, 1H) (ppm).

What reagents are necessary for the following transformation?

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide the major organic product in the reaction below. CH₃CH₂CH₂OH →

When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH₄, what is the primary organic compound which results?

Which of the following is produced by the reaction of (CH₃CH₂)₂S with CH₃CH₂I?

Propose a structure for the ether of formula C₄H₁₀O with the following ¹H NMR signals: δ 1.13 (doublet, 6H), 3.30 (singlet, 3H), 3.65 (septet, 1H) (ppm).