Deck 10: Structure and Synthesis of Alcohols

Question 1

What two atomic orbitals or hybrid atomic orbitals overlap to form the C-O bond in ethanol?

A) C sp² + O sp²
B) C sp³ + O sp³
C) C sp² + O sp³
D) C sp³ + O sp²
E) none of the above

Answer 1

C sp³ + O sp³

Question 2

Provide an acceptable name for the compound below.
HOCH₂CH₂OH

Answer 2

ethylene glycol or ethane-1,2-diol

Question 3

Provide an acceptable name for the compound below.

Answer 3

3-methylcyclopent-3-enol

Question 4

________, commonly used in automobile antifreezes, is a diol which is highly toxic if ingested.

Question 5

What is the correct IUPAC name for the following structure?

A) (Z) 4-methyl-3-hexen-1-thiol
B) (Z) 6-mercapto-3-methylhex-3-ene
C) (E) 6-mercapto-3-methylhex-3-ene
D) (E) 4-methylhex-3-en-1-thiol

Question 6

Provide an acceptable name for the compound below.
(CH₃)₂CHCH₂OH

Question 7

2-Methylpentan-3-ol is classified as ________.

A) a primary alcohol
B) a secondary alcohol
C) a tertiary alcohol
D) a phenol
E) an enol

Question 8

Provide a common name for the following structure.

Question 9

Give the IUPAC name for (CH₃)₂C
CHCH₂CH₂OH.

Question 10

Name the compound shown below.

A) 3-hydroxyethylhexan-3-ol
B) 3-ethylolpentan-2-ol
C) 3-ethylhexan-2,4-diol
D) 4-ethylhexan-3,5-diol

Question 11

2-Methylbutan-1-ol is classified as ________.

A) a primary alcohol
B) a secondary alcohol
C) a tertiary alcohol
D) a phenol
E) an enol

Question 12

Provide an acceptable name for the following compound.

Question 13

________ is dissolved in water to make the solution sold commercially as rubbing alcohol.

Question 14

Consider the alcohol 3-methylpentan-3-ol. Is this alcohol primary, secondary, or tertiary?

Question 15

Provide the IUPAC name for the following compound.

Question 16

1-Methylcyclopentanol is classified as ________.

A) a primary alcohol
B) a secondary alcohol
C) a tertiary alcohol
D) a phenol
E) an enol

Question 17

Provide the IUPAC name for the compound below.

Question 18

________, also known as wood alcohol, is used as a fuel and as a solvent. Ingestion of this alcohol can lead to blindness and death.

Question 19

Provide an acceptable name for the compound below.

Question 20

What type of orbital do the lone pair electrons on oxygen occupy in ethanol?

A) σ
B) π
C) p
D) sp
E) sp³

Question 21

Distillation of mixtures of ethanol and water cannot increase the ethanol content of the mixture above 95% because this solution boils at a lower temperature than either pure ethanol or pure water. The term which describes this lower boiling mixture is ________.

Question 22

What gaseous byproduct is evolved when sodium metal is added to ethanol?

Question 23

Provide an acceptable name for the compound below.

Question 24

Provide an acceptable name for the compound below.

Question 25

Draw (2R, 3S) 2-bromopentan-1,3-diol in a Fischer projection.

Question 26

Provide an acceptable name for the compound below.

Question 27

Which is more soluble in water, butan-1-ol or decan-1-ol? Explain briefly.

Question 28

Provide an acceptable name for the compound below.

Question 29

In a 1-butanol molecule, what part of the molecule is described as hydrophilic?

Question 30

Which of the compounds below has a pK_a that most closely matches the pK_a of ethanol?

A) water
B) ammonia
C) acetic acid
D) phenol
E) HCl

Question 31

What is synthesis gas and what commercially important alcohol is prepared from it?

Question 32

________ is the major intermolecular attraction responsible for the relatively high boiling points of alcohols.

Question 33

Arrange the following alcohols in order of increasing boiling point:
(CH₃)₃COH, CH₃(CH₂)₄OH, (CH₃)₃CCH₂OH, and (CH₃)₂CHCH₂CH₂OH.

Question 34

In a 1-butanol molecule, what part of the molecule is described as hydrophobic?

Question 35

Provide an acceptable name for the compound below.

Question 36

Name the compound shown below.

Question 37

Name the compound shown below.

A) (2S,4R)-4-propylhexane-2-thiol
B) (2R,4S)-4-propylhexane-2-thiol
C) (2S,4R)-4-ethylheptane-2-thiol
D) (2R,4S)-4-ethylheptane-2-thiol

Question 38

What is the correct IUPAC name of the compound below?

A) 3-(2-bromopropyl)-6,6-dimethylheptan-2-ol
B) 5-bromo-3-(3,3-dimethylbutyl)hexan-2-ol
C) 5-(2-bromopropyl)-2,2-dimethylheptan-6-ol
D) 7-bromo-5-(1-hydroxyethyl)-2,2-dimethyloctane

Question 39

Ethanol that contains added impurities that make it unfit for drinking is described as ________.

Question 40

Identify the statement that correctly describes methanol.

A) It is used in alcoholic beverages.
B) It can be used as a fuel source but releases less energy than gasoline when combusted.
C) It once was used as an anesthetic.
D) It is also referred to as rubbing alcohol.

Question 41

Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors reactants or products.
CH₃O^- + HCl →

Question 42

Explain why the synthetic route shown below would be unsuccessful.

Question 43

What reagent(s) are needed to complete the following reaction?

A) 1) LiAlH₄, 2) H₃O⁺
B) 1) NaBH₄, 2) H₃O⁺
C) H₂, Pd
D) 1) DIBAL-H, 2) H₃O⁺

Question 44

Provide the reagents necessary to accomplish the following transformation.
2-methyl-2-octene to 2-methyloctan-3-ol

Question 45

Provide the name of the major organic product that results when 1-pentene is subjected to hydroboration/oxidation.

Question 46

Provide the name of the major organic product that results when 1-pentene is treated with aqueous acid.

Question 47

What is the approximate pKa of phenols?

Question 48

Provide the major organic product of the reaction below.

Question 49

Which is the stronger acid, cyclohexanol or 2-fluorocyclohexan-1-ol?

Question 50

Provide the reagents necessary to carry out the transformation shown below.

Question 51

Provide the reagents necessary to convert (E)-but-2-ene to meso-butane-2,3-diol.

Question 52

Which of the following reagents or sequences do not produce an alcohol or diol from an alkene starting material?

A) H⁺, H₂O
B) HCO₃H
C) BH₃^.THF followed by H₂O₂, NaOH
D) Hg(OAc)₂, H₂O followed by NaBH₄
E) OsO₄, H₂O₂

Question 53

Provide the reagents necessary to convert (R)-3-methylpent-1-ene to

Question 54

Explain why phenol is about 10⁶ times more acidic than methanol. Use appropriate resonance structures as part of your explanation.

Question 55

What is the approximate pKa of alcohols, ROH?

Question 56

Provide a detailed step-by-step mechanism that would account for the formation of the product in the following reaction.

Question 57

Explain how a mixture of phenol and cyclopentanol might be separated using differences in their solubility properties.

Question 58

Rank the following phenols in order of acidity (most acidic = first, least acidic = last).

A) C > A > B
B) A > B > C
C) C > B > A
D) B > C > A

Question 59

Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors reactants or products using pKa values.
CH₃CH₂O^- + NH₃

Question 60

Provide the reagents necessary to carry out the conversion shown below.

Question 61

What sequence of reagents is needed to convert 2-chlorobutane into 3-methyl-4-heptanol?

Question 62

Complete the following reaction by providing a structure for the necessary starting material.

Question 63

Which solvent is not suitable when running a reaction with a Grignard or organolithium reagent?

A) DMSO
B) Tetrahydrofuran
C) Diethyl ether
D) Methanol

Question 64

Which of the following terms best describes the reactive nature of a Grignard reagent?

A) carbocation
B) free radical
C) electrophile
D) nucleophile
E) carbene

Question 65

Provide the structure of the major organic product in the reaction shown below.

Question 66

The reaction of what two compounds produces n-butyllithium?

Question 67

Provide the major organic product of the following reaction.

Question 68

The reaction of CH₃CH₂MgBr with CH₃COCH₂CH₃ gives ________.

A) an achiral product
B) a mixture of diastereomers
C) the racemate of a chiral product
D) a single enantiomer
E) none of the above

Question 69

Reaction of ethylmagnesium bromide with which of the following compounds yields a secondary alcohol after quenching with aqueous acid?

A) H₂CO
B) CH₃CHO
C) (CH₃)₂CO
D) ethylene oxide
E) n-butyllithium

Question 70

Predict the correct product of the following reaction.

Question 71

What reagents are needed to complete the following synthesis?

Question 72

What Grignard reagent and carbonyl compound could be used to prepare 1-ethylcyclohexanol?

Question 73

What reagent is needed to complete the following transformation?

A) iPrMgBr
B) iPrLi
C) (iPr)₂CuLi
D) iPrBr

Question 74

Reaction of ethylmagnesium bromide with which of the following compounds yields a primary alcohol after quenching with aqueous acid?

A) ethyl acetate
B) CH₃CHO
C) (CH₃)₂CO
D) ethylene oxide
E) n-butyllithium

Question 75

Reaction of ethylmagnesium bromide with which of the following compounds yields a tertiary alcohol after quenching with aqueous acid?

A) H₂CO
B) CH₃CHO
C) (CH₃)₂CO
D) ethylene oxide
E) n-butyllithium

Question 76

Identify the structure of the product of the following reaction.

Question 77

Provide the structure of the major organic product in the reaction shown below.

Question 78

Provide the reagents necessary to carry out the multistep synthesis shown below.

Question 79

Provide the major organic product of the following reaction.

Question 80

Why are ether solvents used in the preparation of Grignard and organolithium reagents?