Question 1

Assuming an overall exothermic process,select the potential energy diagram that best represents 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 2

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

Accepted Answer

A)  CH3CH2CH218OH 
B) 
  
C) 
  
D) 
  
E) 
  
A)  CH3CH2CH218OH 
B) 
  
C) 
  
D) 
  
E)

Question 3

Complete the following reaction sequence,giving structures for compounds C and D:

Accepted Answer

The answer of Complete the following reaction sequence,giving structures for...

Question 4

Provide a reasonable synthetic strategy for the synthesis of trans-2-methoxycyclopentanol from bromocyclopentane

Accepted Answer

The answer of Provide a reasonable synthetic strategy for the...

Question 5

Which of these alkyl halide syntheses is predicted to occur at the greatest rate?

Accepted Answer

A)  CH3CH2CH2CH2OH + HI $\rightarrow$ 
B)  (CH3)2CHCH2OH + HBr $\rightarrow$ 
C)  CH3CHOHCH2CH3 + HCl $\rightarrow$ 
D)  CH3CHOHCH2CH3 + HBr $\rightarrow$ 
E)  (CH3)3COH + HI $\rightarrow$ 
A)  CH3CH2CH2CH2OH + HI $\rightarrow$ 
B)  (CH3)2CHCH2OH + HBr $\rightarrow$ 
C)  CH3CHOHCH2CH3 + HCl $\rightarrow$ 
D)  CH3CHOHCH2CH3 + HBr $\rightarrow$ 
E)  (CH3)3COH + HI $\rightarrow$

Question 6

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:
C7H8O
IR - 3325cm−1,strong,broad
1H broad singlet at 2.3 $\delta$ (exchangeable)
2H singlet at 4.6  $\delta$
5H multiplet at 7.3  $\delta$

Accepted Answer

The answer of Propose a structure for the compound with...

Question 7

Draw all of the ethers corresponding to the formula C5H12O,including stereoisomers.

Accepted Answer

Question 8

Which is the best method to prepare 2-ethoxy-5-methylhexane?

Accepted Answer

A)  C2H5ONa + (CH3)2CHCH2CH2Br 
B)  C2H5ONa + (CH3)2CHCH2CH2CH2CH2Br 
C)  C2H5ONa + (CH3)2CHCH2CH2CHBrCH3 
D)  C2H5Br + (CH3)2CHCH2CH2CH(CH3)ONa 
E)  C2H5OH + (CH3)2CHCH2CH2CHOHCH3 + H2SO4,140$\degree$C 
A)  C2H5ONa + (CH3)2CHCH2CH2Br 
B)  C2H5ONa + (CH3)2CHCH2CH2CH2CH2Br 
C)  C2H5ONa + (CH3)2CHCH2CH2CHBrCH3 
D)  C2H5Br + (CH3)2CHCH2CH2CH(CH3)ONa 
E)  C2H5OH + (CH3)2CHCH2CH2CHOHCH3 + H2SO4,140$\degree$C

Question 9

Three-membered rings containing oxygen are called _______________ or ______________.

Accepted Answer

The answer of Three-membered rings containing oxygen are called _______________...

Question 10

Draw structures for all possible ethers having the formula C4H10O

Accepted Answer

Question 11

What is a correct IUPAC name for the following compound?

Accepted Answer

A)  1,2-butanediol 
B)  isopropanol 
C)  1-proanol 
D)  Propylene glycol 
E)  1,2-ethanediol 
A)  1,2-butanediol 
B)  isopropanol 
C)  1-proanol 
D)  Propylene glycol 
E)  1,2-ethanediol

Question 12

What would be the major product of the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  An equimolar mixture of I and II 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  An equimolar mixture of I and II

Question 13

Which compound would have the greatest solubility in water?

Accepted Answer

A)  Diethyl ether 
B)  Methyl propyl ether 
C)  1-Butanol 
D)  1,2-Butanediol 
E)  Pentane 
A)  Diethyl ether 
B)  Methyl propyl ether 
C)  1-Butanol 
D)  1,2-Butanediol 
E)  Pentane

Question 14

Complete the following reaction sequence,giving structural details of all key intermediates:

Accepted Answer

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

Question 15

Which of the following can be described as "optically active,primary alcohol"?

Accepted Answer

A)  CH3CH2CH2CH2CH2OH 
B)  (CH3)2CHCH2CH2OH 
C)  CH3CH2CH(CH3)CH2OH 
D)  (CH3)2CHCHOHCH3 
E)  Two of the above 
A)  CH3CH2CH2CH2CH2OH 
B)  (CH3)2CHCH2CH2OH 
C)  CH3CH2CH(CH3)CH2OH 
D)  (CH3)2CHCHOHCH3 
E)  Two of the above

Question 16

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown:
C6H14O
IR - 1120cm−1,strong,broad
6H triplet at 0.9  $\delta$
4H sextet at 1.5  $\delta$
4H triplet at 3.4  $\delta$

Accepted Answer

The answer of Propose a structure for the compound with...

Question 17

Select the potential energy diagram that best represents 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 18

Which compound would have the lowest boiling point?

Accepted Answer

A)  CH3CH2CH2CH3 
B)  CH3CH2OCH2CH3 
C)  CH3CH2CH2OH 
D)  (CH3)2CHOH 
E)  HOCH2CH2OH 
A)  CH3CH2CH2CH3 
B)  CH3CH2OCH2CH3 
C)  CH3CH2CH2OH 
D)  (CH3)2CHOH 
E)  HOCH2CH2OH

Question 19

If (Z)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  All of the above 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  All of the above 
E)  None of the above

Question 20

The product(s)of 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

Exam 11: Alcohols and Ethers

Assuming an overall exothermic process,select the potential energy diagram that best represents the following reaction:

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

Complete the following reaction sequence,giving structures for compounds C and D:

Provide a reasonable synthetic strategy for the synthesis of trans-2-methoxycyclopentanol from bromocyclopentane

Which of these alkyl halide syntheses is predicted to occur at the greatest rate?

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown: C7H8O IR - 3325cm−1,strong,broad 1H broad singlet at 2.3 δ\deltaδ (exchangeable) 2H singlet at 4.6 δ\deltaδ 5H multiplet at 7.3 δ\deltaδ

Draw all of the ethers corresponding to the formula C5H12O,including stereoisomers.

Which is the best method to prepare 2-ethoxy-5-methylhexane?

Three-membered rings containing oxygen are called _______________ or ______________.

Draw structures for all possible ethers having the formula C4H10O

What is a correct IUPAC name for the following compound?

What would be the major product of the following reaction sequence?

Which compound would have the greatest solubility in water?

Complete the following reaction sequence,giving structural details of all key intermediates:

Which of the following can be described as "optically active,primary alcohol"?

Propose a structure for the compound with the following formula that is consistent with the IR and 1H NMR data shown: C6H14O IR - 1120cm−1,strong,broad 6H triplet at 0.9 δ\deltaδ 4H sextet at 1.5 δ\deltaδ 4H triplet at 3.4 δ\deltaδ

Select the potential energy diagram that best represents the following reaction:

Which compound would have the lowest boiling point?

If (Z)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?

The product(s)of the following reaction

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 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

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Propose a structure for the compound with the following formula that is consistent with the IR and ¹H NMR data shown: C₇H₈O IR - 3325cm⁻¹,strong,broad 1H broad singlet at 2.3 $\delta$ (exchangeable) 2H singlet at 4.6 $\delta$ 5H multiplet at 7.3 $\delta$

Draw all of the ethers corresponding to the formula C₅H₁₂O,including stereoisomers.

Three-membered rings containing oxygen are called _ or .

Draw structures for all possible ethers having the formula C₄H₁₀O

Propose a structure for the compound with the following formula that is consistent with the IR and ¹H NMR data shown: C₆H₁₄O IR - 1120cm⁻¹,strong,broad 6H triplet at 0.9 $\delta$ 4H sextet at 1.5 $\delta$ 4H triplet at 3.4 $\delta$