Deck 6: Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers,thiols, and Thioethers

Question 1

Which of these structures is a tertiary amine?

A)
B)
C)
D)
E)None of these structures are tertiary amines.

Answer 1

Question 2

Which of the following structures is pyrrolidine?

A)
B)
C)
D)
E)

Answer 2

Question 3

Rank the following compounds in order of increasing length of the bond that is shown:

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

Answer 3

IV>II>I>III

Question 4

Which of these statements is false?

A)Amines are both Lewis bases and Brønsted bases.
B)In solution or in the gas phase, the trend for amine basicity is identical.
C)The conjugate acid of an amine is an ammonium ion.
D)Tetrabutyl ammonium chloride cannot form hydrogen bonds in solution.
E)Ammonia is a weaker base than dimethylamine, both in solution and in the gas phase.

Question 5

Which of the following alkyl halides contains the longest carbon-halogen bond?

A)A
B)B
C)C
D)D
E)All the carbon-halogen bonds are the same length.

Question 6

Which of the following statements about amines is false?

A)All amines are capable of forming hydrogen bonds.
B)Amines can be classified as primary, secondary, or tertiary.
C)Amines are weak Brønsted bases.
D)Most amines have a strong, unpleasant odor.
E)In the gas phase, the basicity of amines increases with increasing alkyl substitution.

Question 7

Which of the following is not a diol?

A)
B)
C)
D)
E) All these molecules are diols.

Question 8

Which of these compounds is a secondary amine?

A) CH₃NH₂
B)(CH₃)₂NH
C)(CH₃)₃N
D)CH₃CH₂NH₂
E)(CH₃)₄N⁺Cl^-

Question 9

Which is the correct name for the molecule shown here?

A) 1-chloro-3-iodo-4,6-dimethyl-5-ethylheptane
B) 1-chloro-5-ethyl-3-iodo-4,6-dimethylheptane
C) 1-chloro-3-iodo-5-isopropyl-4-methylheptane
D) 7-chloro-3-ethyl-5-iodo-2,4-dimethylheptane
E) 7 -chloro-5-iodo-3-isopropyl-4-methylheptane

Question 10

Which of the following is the weakest acid in solution?

A) A
B) B
C)C
D) D
E) All have the same acidity.

Question 11

Select the correct name for this molecule.

A) 4-chloro-3,3,5-trimethyl-7-octanol
B) 5 -chloro-6-ethyl-4,6-dimethyl-2-heptanol
C) 5 -chloro- 4,6,6 -trimethyl-2-octanol
D) 3-chloro-2-ethyl-2,4-dimethyl-6-heptanol
E) 3 -chloro-2-ethyl-2,4-methylheptanol

Question 12

Which of the following structures is/are a secondary alkyl halide?

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

Question 13

Which of these statements is false?

A)The lone pair on nitrogen provides a fourth group to complete a tetrahedral arrangement.
B)Amines that possess a stereogenic nitrogen atom interconvert through the inversion process.
C)For simple amines, the barrier to inversion is very low.
D)At the transition state for amine inversion, the amine is planar.
E)If amine inversion is fast, enantiomeric amines can be separated from each other.

Question 14

Which of the following nitrogen-containing compounds is/are chiral at room temperature?

A) I
B) II
C) III
D) II and III
E) I, II, and III

Question 15

Which of the following molecules is the strongest acid?

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

Question 16

For which of the following reactions would you expect K_eq>1?

A)
B)
C)
D)
E)

Question 17

Which of the following can protonate ethanol to a significant extent? The pKa of CH₃CH₂OH₂⁺ is -2.2 .

A) H₂O, pKa=15.7
B) CH₃CH₂OH, pKa=15.9
C) NH₃, pKa=36
D) HCl, pK_a=-7
E) Propanoic acid, pKa=4.9

Question 18

Select the correct name for this molecule.

A) (1 S, 6 R) -bicyclo[6.6.0]dec-3-en-1,6-diol
B) (5 S, 6 R) -bicyclo[4.4.0]dec-2-en-5,6-diol
C) (1 S, 6 R) -bicyclo[4.4.0]dec-3-en-1,6-diol
D) (1 S, 6 R) -bicyclo[4.4.0]dec-8-en-1,6-diol
E) (1 S, 6 R) -bicyclo[4.4.0]oct-2-en-1,6-diol

Question 19

Which of these ammonium ions has the strongest conjugate base?

A)

B)

C)

D)

E) The conjugate bases of all these ammonium ions are equally basic.

Question 20

Which of these structures is ethylene glycol?

A)
B)
C)
D)
E) None of these structures.

Question 21

Provide the IUPAC name for the molecule shown here with correct stereochemistry.

Question 22

Place the following molecules in order of decreasing acidity.

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

Question 23

Provide the IUPAC name for this molecule, including stereochemical designations of stereogenic
carbons.

Question 24

Which of the following statements about organolithium reagents is false?

A)They are strongly basic.
B)They are strongly acidic.
C)They are formed from the reaction of an alkyl halide and lithium metal.
D)They react with water to produce alkanes.
E)They are formed in a radical (one electron transfer) reaction.

Question 25

Boiling point increases as shown in the following series of amines:

Why is the boiling point of (CH₃)₃N lower than that of (CH₃)₂NH?

A) (CH₃)₂NH has a higher molar mass than (CH₃)₃N .
B) (CH₃)₂NH can form hydrogen bonds, but (CH₃)₃ N cannot.
C) (CH₃)₃ N can form hydrogen bonds, but (CH₃)₂NH cannot.
D) (CH₃)₂NH is polar, but (CH₃)₃ N is not.
E) (CH₃)₃N is polar, but (CH₃)₂NH is not.

Question 26

Provide a common name for the molecule shown here.

Question 27

Which of the following compounds do you expect to have the least solubility in water at 25°C?

A) CH₃OH
B)
C) CH₃CH₂OH
D) acetone
E)

Question 28

Draw a correct structure for morpholine.

Question 29

Provide the IUPAC name for the structure shown here.

Question 30

Which of these types of compounds is not able either to form or to accept hydrogen bonds?

A)haloalkanes
B)ethers
C)alcohols
D)primary amines
E)tertiary amines

Question 31

Provide the IUPAC name for the molecule shown here with correct stereochemistry.

Question 32

Draw a correct structure for 4-chloro-2,3-dimethylpentamine.

Question 33

Rank the following compounds from least soluble in water to most soluble.

A) I< II < III
B) IV < II < III < I

C) IV < III < II < I

D) IV < I < II < III

E) IV < II < I < III

Question 34

Which of the following applications would a crown ether typically not be used for?

A)as a chelating agent to remove heavy metals from water
B)to capture minute amounts of precious metals from seawater
C)as a means to indirectly bring reactive anions into nonpolar solvent media
D)to study the chemistry of "host-guest" complexation
E)to stabilize Grignard and organolithium reagents

Question 35

Draw a correct structure for 3-chloro-6-fluoro-5-isopropyl-2-methyloctane.

Question 36

Which of the following solvents is aprotic?

A)acetic acid
B)acetone
C)dimethylamine
D)methanol
E)water

Question 37

Which of the following solvents is/are protic?

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

Question 38

Predict the product of the following reaction:

A)

B)

C)

D)

E)No reaction occurs between the starting material and reagents shown.

Question 39

Which of the structures shown below is not a possible starting material for this reaction sequence?

A)

B)

C)

D)

E) Any of these choices is an appropriate starting material for the transformation shown.

Question 40

Which reagent would you use to accomplish the following transformation?

A) H₂O
B) Mg, Et₂O
C) NH₃
D) H₂/ Raney Ni
E) Any of these reagents could be used.

Question 41

Why is ethanol a stronger acid than tert-butanol in solution?

Question 42

Which of these compounds is more acidic, and why?

Question 43

Which has a higher boiling point, ethanol or propane? Explain.

Question 44

Draw the mechanism showing the Brønsted acid/base reaction between propanoic acid and
methylamine.Show all curved arrows, lone pairs, and nonzero formal charges.Predict the side of
the reaction that will be favored at equilibrium.

Question 45

What is the common name of this molecule?

Question 46

In the gas phase, the order of acidity of the alcohols shown here is reversed. Explain the difference in acidity trends between the gas phase and solution.

Question 47

Predict the product of the following reaction sequence.

Question 48

Distinguish between protic solvents and aprotic solvents and provide at least one example of each.

Question 49

Draw a mechanism for the Brønsted acid/base reaction of ethanol and hydrochloric acid.Show all
curved arrows, lone pairs, and nonzero formal charges.Which side of the reaction is favored at
equilibrium?

Question 50

Draw the conjugate acid and the conjugate base of the compound shown.

Question 51

In the following compounds, identify which proton would be removed first in the presence of
strong base.

Question 52

Draw a correct structure for isopropyl pentyl ether.

Question 53

Which of the following acids is stronger? Explain your reasoning.

Question 54

Predict the product of the following reaction sequence.

Question 55

Draw the conjugate base of the alcohol shown here.Include all lone pairs and nonzero formal
charges.

Question 56

Draw the conjugate base of methylamine.

Question 57

The acidity of alcohols in water follows the following order:
In the gas phase, this order is reversed. Draw an illustration showing how solvent impacts the acidity of the strongest and weakest alcohols in the liquid phase by stabilizing the conjugate base.

Question 58

Question 59

Draw the two products of the following reaction.

Question 60

Draw all the constitutional isomers of the amine with molecular formula C₄H₁₁N. Indicate whether each amine is primary, secondary, or tertiary.

Question 61

Provide a name for this crown ether.

Question 62

Which is more acidic: ethanol or ethanethiol? Explain your answer.

Question 63

There are at least two routes to the product shown using reactions from this chapter.Identify the reagents you would use with each starting material to produce the target molecule.

Question 64

Propose a synthesis of the target molecule from the starting material shown. Show the reagents needed for each step and the product of each step.

Question 65

Provide a synthesis of 1-deutero methylcyclohexane from 1-methylcyclohexene.Show the
reagents used in each step and the intermediates in the synthesis.

Question 66

What is the product of the following reaction?

Question 67

Outline a synthesis of the target molecule shown from the given starting material.You may use
any organic or inorganic reagents.Show the reagents needed for each step and the product of each
transformation.

Question 68

Provide the IUPAC name for this structure.