Deck 11: Alcohols and Ethers

Question 1

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Answer 1

enantiomers.

Question 2

A correct IUPAC name for isobutyl alcohol is:

A) 2-Methyl-1-propanol
B) 2-Methyl-1-butanol
C) 1-Methyl-1-propanol
D) 1,1-Dimethyl-1-ethanol
E) 3-Methyl-1-propanol

Answer 2

2-Methyl-1-propanol

Question 3

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Answer 3

enantiomers.

Question 4

The IUPAC name of compound is:

A) 1,1,1-Triethylmethanol
B) 1,1-Diethyl-1-propanol
C) 2-Ethyl-3-pentanol
D) 3-Ethyl-3-pentanol
E) tert-Heptanol

Question 5

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Question 6

The correct IUPAC name for tert-butyl alcohol is:

A) 1-Butanol
B) 2-Methyl-1-propanol
C) 2-Methyl-2-propanol
D) 2-Butanol
E) 1,1-Dimethyl-1-ethanol

Question 7

The correct IUPAC substitutive name for is:

A) 4-Penten-2-methyl-2-ol
B) 4-Methyl-1-penten-2-ol
C) 2-Methyl-4-penten-2-ol
D) 4-Methyl-1-penten-4-ol
E) 4-Hydroxy-4-methyl-1-pentene

Question 8

Which of these,though often used,is an incorrect common name for (CH₃)₃COH?

A) tert-Butyl alcohol
B) tert-Butanol
C) 2-Methyl-2-propanol
D) More than one is incorrect.
E) Each is a correct name.

Question 9

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Question 10

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

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

Question 11

A correct name for the following Fischer projection formula is:

A) (R)-3-Pentyn-2-ol
B) (S)-3-Pentyn-2-ol
C) (R)-2-Pentyn-4-ol
D) (S)-2-Pentyn-4-ol
E) (S)-2-Hydroxy-3-pentyne

Question 12

What is the correct IUPAC name for the following compound?

A) 4-isopropyl-3,4-dimethyl-2-butanol
B) 2,3,4-trimethyl-4-pentanol
C) 1,1,2,3-tetramethyl-4-pentanol
D) 3,4,5-trimethyl-2-hexanol
E) 3,4,5,5-tetramethyl-2-pentanol

Question 13

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Question 14

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Question 15

What is a correct IUPAC name for the following compound?

A) 1,2-butanediol
B) isopropanol
C) 1-propanol
D) 1,2-propanediol
E) Ethylene glycol

Question 16

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Question 17

Which of these,though often used,is an incorrect common name for CH₃CHOHCH₃?

A) Isopropyl alcohol
B) sec-Propyl alcohol
C) 2-Propanol
D) Isopropanol
E) More than one of these.

Question 18

What is the relationship between alcohols I and II? They are:

A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.

Question 19

What is a correct IUPAC name for the following compound?

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

Question 20

What is the correct IUPAC name for the following compound?

A) 3-methyl-4-ethyl-3-hexen-6-ol
B) 4-ethyl-3-methyl-3,6-hexenol
C) 3-ethyl-4-methyl-3-hexen-1-ol
D) 3-methyl-4-(2-hydroxyethyl)-3-hexene
E) 3-(2-hydroxyethyl)- 3-methyl-3-hexene

Question 21

Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

A) CH₃CH₂CH₂CH₂CH₃
B) CH₃CH₂CH₂CH₂OH
C) CH₃CH₂CH₂OCH₃
D) CH₃CH₂CH₂Cl
E) CH₃CH₂OCH₂CH₃

Question 22

The number of primary alcohols corresponding to the formula C₅H₁₂O,counting stereoisomers separately,is:

A) 1
B) 2
C) 3
D) 4
E) 5

Question 23

Which of the following statements is NOT true of ethers?

A) Ethers are generally unreactive molecules toward reagents other than strong acids.
B) Ethers generally have lower boiling points than alcohols of a corresponding molecular weight.
C) Ethers generally have much lower water solubilities than alcohols with a corresponding molecular weight.
D) Ethers can generally be cleaved by heating them with strong acids.
E) Ethers form peroxides when allowed to stand in the presence of oxygen.

Question 24

The number of optically active pentyl alcohols (C₅H₁₁OH),i.e. ,the total number of individual enantiomers,is:

A) 0
B) 2
C) 3
D) 4
E) 6

Question 25

Which compound would have the lowest boiling point?

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

Question 26

What is the total number of pentyl alcohols,including stereoisomers?

A) 7
B) 8
C) 9
D) 10
E) 11

Question 27

Which compound would have the highest boiling point?

A) CH₃CH₂CH₂CH₃
B) CH₃CH₂OCH₃
C) CH₃CH₂CH₂OH
D) (CH₃)₂CHOH
E) HOCH₂CH₂OH

Question 28

Today,most industrial ethanol is made in the U.S.by the:

A) fermentation of grain.
B) hydrolysis of ethyl bromide.
C) hydration of ethylene.
D) reduction of acetaldehyde.
E) hydration of acetylene.

Question 29

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

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

Question 30

The major industrial process in use today for the production of methanol is the:

A) hydration of ethyne.
B) distillation of wood.
C) hydrogenation of carbon dioxide.
D) reduction of methanal.
E) catalytic reduction of carbon monoxide.

Question 31

Which compound would have the highest boiling point?

A) CH₃CH₂CH₂CH₃
B) CH₂(OH)CH(OH)CH₂OH
C) CH₃CH₂CH₂OH
D) (CH₃)₂CHOH
E) HOCH₂CH₂OH

Question 32

Which compound would have the lowest boiling point?

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

Question 33

Which is a correct IUPAC name for CH₃CH₂OCH₂CH₂CH₂OCH₂CH₃?

A) 1,4-Dioxane
B) Ethylene glycol diethyl ether
C) 1,3-Diethoxypropane
D) 1,2-Diethoxyethane
E) 1,2-Diethoxymethane

Question 34

Which compound would have the lowest solubility in water?

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

Question 35

Which compound would have the greatest solubility in water?

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

Question 36

The number of secondary alcohols corresponding to the formula C₅H₁₂O,counting stereoisomers separately,is:

A) 1
B) 2
C) 3
D) 4
E) 5

Question 37

The total number of ethers corresponding to the formula C₅H₁₂O,counting stereoisomers separately,is:

A) 4
B) 5
C) 6
D) 7
E) 8

Question 38

What is the most accurate name for the molecule represented by the following Fischer projection formula?

A) sec-Butyl methyl ether
B) Isobutyl methyl ether
C) tert-Butyl methyl ether
D) (R)-2-Methoxybutane
E) (S)-2-Methoxybutane

Question 39

The number of tertiary alcohols corresponding to the formula C₅H₁₂O,counting stereoisomers separately,is:

A) 1
B) 2
C) 3
D) 4
E) 5

Question 40

Which product(s)would you expect to obtain from the following sequence of reactions?

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

Question 41

Which would be the best method for converting 3,3-dimethyl-1-pentene into 3,3-dimethyl-2-pentanol?

A) H₃O⁺,heat
B) BH₃:THF;then H₂O₂,OH^-
C) concd.H₂SO₄;then H₂O,heat
D) Hg(OAc)₂/THF-H₂O;then NaBH₄,OH^-
E) HBr;then NaOH/H₂O

Question 42

Which of the following would be a reasonable synthesis of 2-butanol?

A)

B)

C)

D)

E) None of these

Question 43

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

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

Question 44

Which of the following would be a reasonable synthesis of CH₃CH₂CH₂CH₂OH?

A)

B)

C)

D)

E) None of these

Question 45

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

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

Question 46

Which of the alcohols listed below would you expect to react most rapidly with HBr?

A) CH₃CH₂CH₂CH₂CH₂CH₂OH
B) (CH₃CH₂)₂CH₂CH₂OH
C) (CH₃CH₂)₂CHOHCH₃
D) CH₃CH₂CH₂CH₂CH₂OH
E) (CH₃CH₂)₂C(CH₃)OH

Question 47

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

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

Question 48

Oxymercuration-demercuration of 3-methylcyclopentene produces this/these product(s):

A) I
B) II
C) III
D) IV
E) Both III and IV

Question 49

Which of the following could not be used to synthesize 2-bromopentane efficiently?

A) 1-Pentene + HBr $\rightarrow$
B) 2-Pentene + HBr $\rightarrow$
C) 2-Pentanol + HBr $\rightarrow$
D) 2-Pentanol + PBr₃ $\rightarrow$
E) All of the above would afford good yields of 2-bromopentane.

Question 50

Which statement is true concerning the formation of alcohols by the hydroboration-oxidation sequence?

A) Overall,the process results in syn addition and anti-Markovnikov orientation.
B) Overall,the process results in anti addition and anti-Markovnikov orientation.
C) Overall,the process results in syn addition and Markovnikov orientation.
D) Overall,the process results in anti addition and Markovnikov orientation.
E) The stereochemistry and orientation are unpredictable.

Question 51

What is the electrophilic species involved in the initial step of the reaction below?

A) "⁺OH"
B) "⁺HgOAc"
C) "H₃O⁺"
D) "THF"
E) "the THF/H₂O complex"

Question 52

The hydroboration-oxidation procedure can be successfully employed for synthesis of deuterated derivatives,by using BD₃ instead of BH₃.What product would you expect from the following reaction?

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

Question 53

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

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

Question 54

Which would be the major product of the reaction shown?

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

Question 55

Which alcohol would undergo acid-catalyzed dehydration most rapidly?

A) 3,3-dimethyl-1-butanol
B) 2,2-dimethyl-1-butanol
C) 3,3-dimethyl-2-butanol
D) 2-methyl-2-butanol
E) All would undergo dehydration equally rapidly.

Question 56

Anti-Markovnikov hydration of the carbon-carbon double bond occurs when an alkene reacts with:

A) BH₃:THF;then H₂O₂/OH^-
B) BH₃:THF;then CH₃COOH
C) Hg(OAc)₂,THF,H₂O;then NaBH₄,OH^-
D) Hg(OAc)₂,THF,CH₃OH;then NaBH₄,OH^-
E) Hg(OAc)₂,THF,H₂O;then BH₃:THF

Question 57

What is the nucleophilic species involved in the initial step of the reaction below?

A) "^-OH"
B) "Hg(OAc)₂"
C) "H₂O"
D) "cyclopentene"
E) "the THF/H₂O complex"

Question 58

Which would be the best way to carry out the following synthesis?

A) (1)HA,heat; (2)H₃O⁺,H₂O,heat
B) (1)(CH₃)₃COK / (CH₃)₃COH; (2)BH₃:THF,then H₂O₂,OH^-
C) (1)(CH₃)₃COK / (CH₃)₃COH; (2)H₃O⁺,then H₂O,heat
D) (1)KOH,C₂H₅OH; (2)BH₃:THF,then H₂O₂,OH^-
E) (1)KOH,C₂H₅OH; (2)HA,heat; (3)H₃O⁺,H₂O,heat

Question 59

The oxymercuration-demercuration procedure can be successfully employed for synthesis of deuterated derivatives,by using NaBD₄ instead of NaBH₄ in the second step.What product would you expect from the following reaction?

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

Question 60

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

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

Question 61

Which of the following could be used to synthesize 2-chlorobutane?

A) CH₃CH₂CH $\equiv$ CH₂ + Cl₂ (aq) $\rightarrow$
B) CH₃CH₂C $\equiv$ CH₃ + HCl $\rightarrow$
C) CH₃CH₂C $\equiv$ CH + HCl $\rightarrow$
D) CH₃CH₂C $\equiv$ CH + Cl₂ $\rightarrow$
E) None of the above

Question 62

cis-3-Methylcyclopentanol is treated with CH₃SO₂Cl in the presence of a base.The product of the reaction then is allowed to react with KI in methanol.What is the final product?

A) trans-1-Iodo-3-methylcyclopentane
B) cis-1-Iodo-3-methylcyclopentane
C) 1-Methylcyclopentene
D) 2-Methylcyclopentene
E) 3-Methylcyclopentene

Question 63

trans-3-Methylcyclopentanol is treated with CH₃SO₂Cl in the presence of base.The product of this reaction is then heated with KI in methanol.What is the final product?

A) trans-1-Iodo-3-methylcyclopentane
B) cis-1-Iodo-3-methylcyclopentane
C) 1-Methylcyclopentene
D) 2-Methylcyclopentene
E) 3-Methylcyclopentene

Question 64

Which of the alcohols listed below would you expect to react most rapidly with PBr₃?

A) CH₃CH₂CH₂CH₂CH₂CH₂OH
B) (CH₃CH₂)₂CH(OH)CH₂CH₃
C) (CH₃CH₂)₂CHOHCH₃
D) (CH₃CH₂)₃COH
E) (CH₃CH₂)₂C(CH₃)OH

Question 65

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

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

Question 66

Which of the following could be used to synthesize 1-bromobutane efficiently?

A) CH₃CH₂CH=CH₂ + HBr $\rightarrow$
B) CH₃CH₂CH₂CH₂OH + PBr₃ $\rightarrow$
C) CH₃CH₂CH₂(OH)CH₃ + HBr $\rightarrow$
D) CH₃CH₂CH₂CH₂OH + Br₂ $\rightarrow$
E) None of these

Question 67

Which reagent(s)would transform propyl alcohol into propyl bromide?

A) Concd.HBr and heat
B) PBr₃
C) NaBr/H₂O and heat
D) More than one of these
E) All of these

Question 68

The conversion of 3-methyl-1-octanol to 1-chloro-3-methyloctane is best achieved through use of which of these reagents?

A) "Concd.HCl"
B) "SO₂Cl₂"
C) "NaCl,H₂SO₄"
D) "PCl₃"
E) " POCl₃"

Question 69

Which of the following could be used to synthesize 2-iodobutane?

A) CH₃CH₂CH $\equiv$ CH₂ + I₂ (aq) $\rightarrow$
B) CH₃CH₂C $\equiv$ CH₃ + HI $\rightarrow$
C) CH₃CH₂C $\equiv$ CH + HI $\rightarrow$
D) CH₃CH₂C $\equiv$ CH + I₂ $\rightarrow$
E) None of the above

Question 70

Which of the following could be used to synthesize 1-bromopentane?

A) CH₃CH₂CH₂CH=CH₂ + HBr $\rightarrow$
B) CH₃CH₂CH₂CH₂CH₂OH + PBr₃ $\rightarrow$
C) CH₃CH₂CH₂CH₂CH₂OH + NaBr $\rightarrow$
D) CH₃CH₂CH₂CH₂CH₂OH + Br₂ $\rightarrow$
E) CH₃CH₂CH₂CH=CH₂ + Br₂ $\rightarrow$

Question 71

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

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

Question 72

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

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

Question 73

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

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

Question 74

The conversion of is best achieved through use of which of these reagents in a low temperature reaction?

A) Concd.HBr
B) Br₂
C) NaBr,H₂SO₄
D) PBr₃
E) HBr,peroxide

Question 75

Which compound is a tosylate?

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

Question 76

The following reaction, is probably:

A) an S_N1-type reaction involving the protonated alcohol as the substrate.
B) an S_N2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.

Question 77

The major product of the following reaction would be:

A) I
B) II
C) III
D) Equal amounts of I and II
E) None of these

Question 78

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

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

Question 79

Which of the following could be used to synthesize 2-bromobutane?

A) CH₃CH₂CH $\equiv$ CH₂ + Br₂ (aq) $\rightarrow$
B) CH₃CH₂C $\equiv$ CH₃ + HBr $\rightarrow$
C) CH₃CH₂C $\equiv$ CH + HBr $\rightarrow$
D) CH₃CH₂C $\equiv$ CH + Br₂ $\rightarrow$
E) More than one of the above

Question 80

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

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