Question 1

What is the correct assignment of the acid, base, conjugate acid and conjugate base in the following equilibrium?  &#10;A) 1 = acid; 2 = base; 3 = conjugate acid; 4 = conjugate base&#10;B) 1 = acid; 2 = base; 3 = conjugate base; 4 = conjugate acid&#10;C) 1 = base; 2 = acid; 3 = conjugate acid; 4 = conjugate base&#10;D) 1 = base; 2 = acid; 3 = conjugate base; 4 = conjugate acid

Accepted Answer

In the given equilibrium, the compound donating a proton (H+) is the acid (1), and the compound accepting the proton is the base (2). When the acid donates a proton, it forms its conjugate base (3), and when the base accepts a proton, it forms its conjugate acid (4). Therefore, 1 = acid, 2 = base, 3 = conjugate base, and 4 = conjugate acid. Choice B correctly matches all the terms with their correct identities.

Question 2

What is the IUPAC name of the following compound?  &#10;A) (R)-4-methyl-2-hexyne&#10;B) (S)-4-methyl-2-hexyne&#10;C) (R)-3-methyl-4-hexyne&#10;D) (S)-3-methyl-4-hexyne

Accepted Answer

The longest chain of carbons in the molecule is six carbons long, giving it the prefix "hex". The triple bond is located between the second and third carbons, giving it the suffix "-yne". The substituent on the fourth carbon is a methyl group, which is designated with the prefix "4-methyl-". The stereochemistry at the second carbon is determined by assigning priority to the two substituents attached to it (one carbon and one hydrogen) and then determining the direction of rotation from the higher-priority group to the lower-priority group. In this case, the carbon has a higher atomic number than the hydrogen, so the higher-priority group is on the same side as the hydrogen, giving it the (S) configuration. Therefore, the correct IUPAC name is (S)-4-methyl-2-hexyne.

Question 3

What is the IUPAC name of the following compound?  &#10;A) 3,4-dimethyl-1-hexen-5-yne&#10;B) 4-ethynyl-2-vinylbutane&#10;C) 3-methyl-4-vinyl-1-pentyne&#10;D) 4-ethynyl-3-methyl-1-pentyne

Accepted Answer

3,4-dimethyl-1-hexen-5-yne

Question 4

What is the approximate C-C-C bond angle in propyne?&#10;A) 90$\degree$&#10;B) 109$\degree$&#10;C) 120$\degree$&#10;D) 180$\degree$

Accepted Answer

In propyne, the central carbon is sp hybridized, resulting in a linear geometry with a bond angle of approximately 180$\degree$.

Question 5

How many alkynes are there with the molecular formula C₆H₁₀? A) 4 B) 5 C) 6 D) 7

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Question 6

Which sequence of reactions can be used to convert 1-pentene to 1-pentyne A) Treatment with HBr; followed by treatment with NaOH B) Treatment with Br₂; followed by treatment with NaNH₂ C) Treatment with Br₂; followed by treatment with H₂SO₄ D) Treatment with Br₂, H₂O; followed by treatment with NaOH

Accepted Answer

The conversion of an alkene to an alkyne typically involves a two-step process: first adding a halogen (such as Br2) to the alkene to form a vicinal dihalide, and then removing one of the halogen atoms using a strong base (such as NaNH2) to form the alkyne. In this case, option B involves using Br2 (written as Br-S-B) to form 1,5-dibromopentane, which can then be deprotonated using NaNH2 to form 1-pentyne. Option A is not a viable choice because treatment with HBr alone would result in the formation of 1-bromopentane. Option C involves using NaHS (a weaker base) instead of NaNH2, which would likely not be strong enough to remove one of the halogen atoms from 1,5-dibromopentane. Option D involves using both HBr and NaOH, but this combination of reagents would result in the formation of 1-bromopentene rather than 1-pentyne.

Question 7

How many terminal alkynes are there with the molecular formula C₇H₁₂? A) 5 B) 7 C) 8 D) 9

Accepted Answer

To be a terminal alkyne, the molecule must have a carbon-carbon triple bond at the end of the carbon chain. In the given molecular formula, there are 8 carbons, but only 2 of them are connected to another carbon atom. Therefore, there are only 2 possible locations for a triple bond, giving us a total of 2 terminal alkynes. The answer is C, which corresponds to 8.

Question 8

What is the IUPAC name of the following compound? CH₃CH₂CH₂-CºC-CH(CH₃)₂ A) 1-isopropyl-1-pentyne B) 2-methyl-3-heptyne C) 6-methyl-4-heptyne D) isopropyl propyl ethyne

Accepted Answer

The compound can be simplified as follows:

CH3-CH(CH3)-C≡C-CH(CH3)-CH2-CH(CH3)-CH2-CH3

The longest carbon chain is 7 carbons, so the parent chain is heptane. The triple bond is located between carbons 2 and 3, so the name starts with "2-methyl-3-". There is a methyl group on carbon 6 and a methyl group on the terminal carbon, which gives the name "2-methyl-3-heptyne". Therefore, the correct answer is B.

Question 9

What is the major organic product obtained from the following reaction?  &#10;A) cyclohexyne&#10;B) 1,3-cyclohexadiene&#10;C) cyclohexene&#10;D) 1,2-diaminocyclohexane

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Question 10

What is the IUPAC name of the following compound  &#10;A) vinylcyclohexane&#10;B) allylcyclohexane&#10;C) ethynylcyclohexane&#10;D) acetylcyclohexane

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Question 11

Which atomic orbitals overlap to form the carbon-carbon triple bond of an alkyne? A) 2s + 2s; sp + sp; 2p + 2p B) sp + sp; sp + sp; 2p + 2p C) sp + sp; 2p + 2p; 2p + 2p D) sp² + sp²; sp + sp; 2p + 2p

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Question 12

Approximately how long is a carbon-carbon triple bond of an alkyne?&#10;A) 110 pm&#10;B) 121 pm&#10;C) 135 pm&#10;D) 156 pm

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Question 13

Which sequence of reactions can be used to convert (Z) 2-pentene to 2-pentyne A) Treatment with Br₂; followed by treatment with NaNH₂ B) Treatment with Br₂, H₂O; followed by treatment with NaOH C) Treatment with Br₂; followed by treatment with H₂SO₄ D) Treatment with HBr; followed by treatment with NaOH

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Question 14

What is the major organic product obtained from the following reaction?  &#10;A) (E) 2-butene&#10;B) (Z) 2-butene&#10;C) 2-butyne&#10;D) 1-butyne

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Question 15

Which of the following has the lowest pK_a? A) butane B) 1-butene C) 1-butyne D) 2-butyne

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Question 16

Which of the following is the strongest acid?&#10;A) propane&#10;B) cyclopropane&#10;C) propene&#10;D) propyne

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Question 17

What is the IUPAC name for the following compound?  &#10;A) (R)-3-methyl-1-penten-4-yne&#10;B) (S)-3-methyl-1-penten-4-yne&#10;C) (R)-4-methyl-4-penten-1-yne&#10;D) (S)-4-methyl-4-penten-1-yne

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Question 18

What is the smallest cycloalkyne that is stable at room temperature?&#10;A) cyclohexyne&#10;B) cyclononyne&#10;C) cyclododecyne&#10;D) cycloeicosyne

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Question 19

Which atomic orbitals overlap to form the carbon-carbon single bond of 1-propyne? A) 2s + sp B) sp + sp² C) sp + sp³ D) sp² + sp³

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Question 20

What is the IUPAC name of the following compound? (CH₃)₂CHCH₂-CºC-CH(CH₃)₂ A) 2,6-dimethyl-3-heptyne B) 2,6-dimethyl-4-heptyne C) 1,1,5,5-tetramethyl-2-pentyne D) 4-nonyne

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Question 21

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 22

What is the major organic product obtained from the following reaction?  &#10;A) 3,4-dibromohexane&#10;B) 3,3-dibromohexane&#10;C) (Z) 3,4-dibromohexene&#10;D) 3,3,4,4-tetrabromohexane

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Question 23

What is the major organic product obtained from the following reaction?  &#10;A) 2,3-dibromobutane&#10;B) 2,2,3,3-tetrabromobutane&#10;C) 2,3-dibromobutene&#10;D) 2,2-dibromobutane

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Question 24

What is the major organic product obtained from the following reaction?  &#10;A) 2-methyl-3-hexene&#10;B) 2-methyl-3-heptyne&#10;C) 2-bromo-3-methylbutane&#10;D) 2-methyl-2-butene

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Question 25

What is the major organic product obtained from the following reaction?  &#10;A) 3,4-dibromohexane&#10;B) 3,3-dibromohexane&#10;C) (E) 3,4-dibromohexene&#10;D) 3,3,4,4-tetrabromohexane

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Question 26

What type of intermediate s formed in the Hg^2- catalyzed hydration of an alkyne?? A) an alcohol B) an enol C) a 1,2-diene D) an epoxide

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Question 27

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 28

What is the major organic product obtained from the following reaction?  &#10;A) butanal&#10;B) cis-2-butene&#10;C) 2-butanol&#10;D) butanone

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Question 29

What is the major organic product obtained from the following reaction?  &#10;A) butanal&#10;B) cis-2-butene&#10;C) 2-butanol&#10;D) butanone

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Question 30

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 31

What is the major organic product obtained from the following reaction?  &#10;A) (E) 3,4-dibromohexene&#10;B) (Z) 3,4-dibromohexene&#10;C) (E) 2,3-dibromohexene&#10;D) (Z) 2,3-dibromobutene

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Question 32

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 33

What is the major organic product obtained from the following reaction?  &#10;A) 2-hexanone&#10;B) hexanal&#10;C) 2-hexanol&#10;D) cis-2-hexene

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Question 34

What is the major organic product obtained from the following reaction?  &#10;A) 1-methyl-4-nonyne&#10;B) 2-methyl-4-nonyne&#10;C) 2-methyl-3-nonyne&#10;D) 3-methyl-4-nonyne

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Question 35

What is the major organic product obtained from the following reaction?  &#10;A) (E) 1,2-dibromobutene&#10;B) (Z) 1,2-dibromobutene&#10;C) (E) 2,3-dibromobutene&#10;D) (Z) 2,3-dibromobutene

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Question 36

What is the major organic product obtained from the following reaction?  &#10;A) 2-hexanone&#10;B) hexanal&#10;C) 2-hexanol&#10;D) cis-2-hexene

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Question 37

What is the major organic product obtained from the following reaction?  &#10;A) 2,3-dibromobutane&#10;B) 2,2,3,3-tetrabromobutane&#10;C) 2,3-dibromobutene&#10;D) 2,2-dibromobutane

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Question 38

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 39

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 40

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 41

What is the major organic product obtained from the following series of reactions?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 42

What is the best choice of reagent(s) to perform the following transformation? A) H₂/Lindlar catalyst B) Na/NH₃ C) (sia)₂BH; followed by H₂O₂, NaOH D) BH₃; followed by H₂O₂, NaOH

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Question 43

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 44

What is the best choice of reagent(s) to perform the following transformation? A) H₂/Lindlar catalyst B) Na/NH₃ C) (sia)₂BH; followed by H₂O₂, NaOH D) BH₃; followed by H₂O₂, NaOH

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Question 45

What is the major organic product obtained from the following series of reactions? A) propanal, CH₃CH₂CHO B) 1-propanol, CH₃CH₂CH₂OH C) butanal, CH₃CH₂CH₂CHO D) butanone, CH₃COCH₂CH₃

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Question 46

What is the best choice of reagent(s) to perform the following transformation? A) 1 mole of Br₂ B) 2 moles of Br₂ C) 1 mole of HBr D) 2 moles of HBr

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Question 47

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 48

What is the major organic product obtained from the following series of reactions?  &#10;A) (Z)-2-heptene&#10;B) (Z)-1,5-heptene&#10;C) 1-heptene&#10;D) heptane

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Question 49

What is the best choice of reagent(s) to perform the following transformation? A) H₂/Pt B) H₂/Lindlar catalyst C) Na/NH₃ D) BH₃; followed by H₂O₂, NaOH

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Question 50

What is the major organic product obtained from the following reaction?  &#10;A) 1&#10;B) 2&#10;C) 3&#10;D) 4

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Question 51

What is the major organic product obtained from the following reaction?  &#10;A) butane&#10;B) 1-butene&#10;C) cis-2-butene&#10;D) trans-2-butene

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Question 52

Which of the following reagents react with 2-butyne to form (Z)-2-butene  &#10;A) only 1&#10;B) only 2&#10;C) only 3&#10;D) only 1 and 2

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Question 53

What is the best choice of reagent(s) to perform the following transformation? A) H₂O; H₂SO₄ B) 1. 3 moles of NaNH₂; 2. H₃O⁺ C) KMnO₄, NaOH, H₂O D) Zn

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Question 54

What is the major organic product obtained from the following reaction?  &#10;A) butane&#10;B) 1-butene&#10;C) cis-2-butene&#10;D) trans-2-butene

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Question 55

What is the major organic product obtained from the following series of reactions?  &#10;A) (E)-5-phenyl-2-pentene&#10;B) 6-phenyl-1-hexene&#10;C) (Z)-6-phenyl-2-hexene&#10;D) (E)-6-methyl-3-heptene

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Question 56

What is the major organic product obtained from the following series of reactions?  &#10;A) (Z)-2-heptene&#10;B) (E)-2-heptene&#10;C) 1-heptene&#10;D) heptane

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Question 57

Which of the following reagents react with 2-butyne to form butane A) H₂/Lindlar catalyst B) H₂/Pd C) (sia)₂BH followed by CH₃COOH D) Na/NH₃

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Question 58

What is the best choice of reagent(s) to perform the following transformation? A) 1 mole of Br₂ B) 2 moles of Br₂ C) 1 mole of HBr D) 2 moles of HBr

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Question 59

What is the major organic product obtained from the following reaction?  &#10;A) butane&#10;B) 1-butene&#10;C) cis-2-butene&#10;D) trans-2-butene

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Question 60

What is the best choice of reagent(s) to perform the following transformation? A) H₂/Pt B) H₂/Lindlar catalyst C) Na/NH₃ D) BH₃; followed by H₂O₂, NaOH

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Question 61

What is IUPAC name of the following compound?&#10;

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Question 62

What is the major organic product obtained from the following reaction?&#10;

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Question 63

What is the major organic product obtained from the following reaction?&#10;

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Question 64

Outline how one might achieve the following transformation, showing reagents and the isolated intermediates in the synthetic scheme.&#10;

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Deck 7: Alkynes