Deck 10: Structure and Synthesis of Alcohols

Question 1

Provide an acceptable name for the compound below.
HOCH₂CH₂OH

Answer 1

ethylene glycol or ethane-1,2-diol

Question 2

Provide the IUPAC name for the compound below.

Answer 2

3,4,5-triethyloctan-3-ol

Question 3

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

Answer 3

a primary alcohol

Question 4

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 5

Provide an acceptable name for the compound below.

Question 6

Provide an acceptable name for the following compound.

Question 7

________, 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 8

Provide an acceptable name for the compound below.

Question 9

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

Question 10

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

Question 11

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

Question 12

1-Methylcyclopentanol is classified as ________.

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

Question 13

Name the compound shown below.

Question 14

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 15

What two atomic orbitals or hybrid atomic orbitals overlap to form the C­O 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

Question 16

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

Question 17

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 18

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

Question 19

Provide a common name for the following structure.

Question 20

Provide the IUPAC name for the following compound.

Question 21

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

Question 22

Provide an acceptable name for the compound below.

Question 23

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

Question 24

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 25

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

Question 26

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 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 hydrophobic?

Question 30

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

Question 31

Name the compound shown below.

Question 32

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 33

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

Question 34

Name the compound shown below.

Question 35

Provide an acceptable name for the compound below.

Question 36

Provide an acceptable name for the compound below.

Question 37

Provide an acceptable name for the compound below.

Question 38

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

Question 39

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

Question 40

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 41

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

Question 42

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

Question 43

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

Question 44

Provide the major organic product of the following reaction.

Question 45

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

Question 46

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

Question 47

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 48

Explain why the synthetic route shown below would be unsuccessful.

Question 49

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

Question 50

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

Question 51

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

Question 52

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

Question 53

Which is the stronger acid, phenol or 4-nitrophenol?

Question 54

Provide the major organic product of the following reaction.

Question 55

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

Question 56

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

Question 57

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 58

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

Question 59

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

Question 60

Provide the major organic product of the reaction below.

Question 61

Provide the major organic product of the following reaction.

Question 62

Predict the correct product of the following reaction.

Question 63

What reagents are needed to complete the following synthesis?

Question 64

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

Question 65

Provide the major organic product of the following reaction.

Question 66

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

Question 67

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 68

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 69

What reagent is needed to complete the following transformation?

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

Question 70

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

Question 71

The reaction of what two compounds produces n-butyllithium?

Question 72

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

Question 73

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

Question 74

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 75

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 76

Identify the structure of the product of the following reaction.

Question 77

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

Question 78

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 79

What series of synthetic steps could be used to carry out the transformation shown below?

Question 80

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