Question 1

Arrange these carbocations in order of increasing stability (least to most).

Accepted Answer

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Question 2

Which reagents react with an alkene by anti addition? i. Cl₂ II. Br₂ III. H₂/Pt IV. BH₃, followed by H₂O₂/NaOH/H₂O

Accepted Answer

Cl2 and Br2 react with alkenes by anti addition, where the halogens add to opposite sides of the double bond.

Question 3

Which are the major products from the reaction of 1,2-dimethylcyclohexene with H₂/Pt?

Accepted Answer

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Question 4

Compound X has a molecular formula C₈H₁₄ and reacts with H₂/Pt to give compound Y, C₈H₁₆. Which is compound X?

Accepted Answer

Compound X has alternating sulfur and boron atoms, with one carbon and one hydrogen atom in between each pair. Since compound I fits this description and it undergoes the reaction described to form compound Y, it must be X.

Question 5

Which compound has the most exothermic (most negative) heat of hydrogenation?

Accepted Answer

The heat of hydrogenation measures the stability of an alkene through the addition of hydrogen. The more negative the value, the more stable the alkene. Looking at the structures given, it can be observed that compound II has two double bonds in a cis configuration, which is the most unstable geometry for a double bond due to steric hindrance. Additionally, compound II has an electron-withdrawing nitro group, making it more reactive towards hydrogenation. Therefore, compound II will have the most negative heat of hydrogenation, making choice B the correct answer.

Question 6

Which reagents react with 2-methyl-1-hexene in a Markovnikov orientation? i. HBr II. H₂O/H₂SO₄ III. Br₂ IV. BH₃, followed by H₂O₂/NaOH/H₂O

Accepted Answer

Both HBr and the reagent in II (hydrogen sulfide with sulfuric acid) add in a Markovnikov orientation, meaning that the electrophile (H or ₂) adds to the carbon with the most hydrogens. Reagents III and IV do not add in a Markovnikov orientation.

Question 7

Which energy diagram represents the reaction of HBr with 2-butene?

Accepted Answer

Energy diagram II shows the reaction of HBr with 2-butene. This is because it shows an exothermic reaction with a decrease in energy from reactants to products, which is characteristic of addition reactions. The other energy diagrams do not show this type of reaction or have higher energy products compared to reactants.

Question 8

Which is the major product from the reaction of 1,2-dimethylcyclohexene with Br₂?

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Question 9

Which reagents react with an alkene by syn addition? i. Cl₂ II. Br₂ III. H₂/Pt IV. BH₃, followed by H₂O₂/NaOH/H₂O

Accepted Answer

III (H2/Pt) and IV (BH3, followed by H2O2/NaOH/H2O) both react with alkenes through syn addition mechanisms.

Question 10

The hydroboration and subsequent oxidation of 1-heptene leads to which of the following products?

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Question 11

Ethynylcyclohexane reacts with sodium amide. The product of that reaction then reacts with bromocyclohexane. What is the main product that is formed?

Accepted Answer

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Question 12

Which is the major product from the reaction of cyclopentene with Br₂/CCl₄?

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Question 13

Which compound does not give two stereoisomers when reacted with Cl₂/CCl₄?

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Question 14

Select the stereoselective reagents from the following list. HCl H⁺/H₂O Br₂ BH₃ H₂

Accepted Answer

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Question 15

Which is the product of the reaction of 1-methylcyclohexene with H₂O/H₂SO₄?

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Question 16

Which set of reagents will produce a electrophilic addition to the pi bond of an alkene?? i. H₂O/H₂SO₄ II. Br₂/CCl₄ III. HBr IV. H₂/Pt

Accepted Answer

Electrophilic addition to the pi bond of an alkene can be achieved with reagents that can provide a strong electrophile. Reagents in options I (H2O/H2SO4), II (Br2/CCl4), and III (HBr) all can act as electrophiles or generate electrophiles that add to alkenes. Option IV (H2/Pt) is used for hydrogenation, not electrophilic addition.

Question 17

Which point on the energy diagram represents the intermediate?

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Question 18

Which statement does not describe a transition state?

Accepted Answer

Transition states are short-lived species and cannot be isolated or directly observed experimentally.

Question 19

But-1-yn-1-ylcyclohexane reacts with molecular hydrogen under pressure in the presence of a Lindlar catalyst. What reaction product is formed?

Accepted Answer

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Question 20

Which is the major product from acid catalyzed hydration of 2-methyl-2-pentene?

Accepted Answer

Acid catalyzed hydration of 2-methyl-2-pentene results in the addition of water to form an alcohol. The most stable carbocation intermediate is formed with the addition of water to the more substituted carbon atom, leading to the formation of 2-methyl-2-pentanol as the major product.

Quiz 1: Covalent Bonding and Shapes of Molecules

Arrange these carbocations in order of increasing stability (least to most) .

Which reagents react with an alkene by anti addition? i. Cl₂ II. Br₂ III. H₂/Pt IV. BH₃, followed by H₂O₂/NaOH/H₂O

Which are the major products from the reaction of 1,2-dimethylcyclohexene with H₂/Pt?

Compound X has a molecular formula C₈H₁₄ and reacts with H₂/Pt to give compound Y, C₈H₁₆. Which is compound X?

Which compound has the most exothermic (most negative) heat of hydrogenation?

Which reagents react with 2-methyl-1-hexene in a Markovnikov orientation? i. HBr II. H₂O/H₂SO₄ III. Br₂ IV. BH₃, followed by H₂O₂/NaOH/H₂O

Which energy diagram represents the reaction of HBr with 2-butene?

Which is the major product from the reaction of 1,2-dimethylcyclohexene with Br₂?

Which reagents react with an alkene by syn addition? i. Cl₂ II. Br₂ III. H₂/Pt IV. BH₃, followed by H₂O₂/NaOH/H₂O

The hydroboration and subsequent oxidation of 1-heptene leads to which of the following products?

Ethynylcyclohexane reacts with sodium amide. The product of that reaction then reacts with bromocyclohexane. What is the main product that is formed?

Which is the major product from the reaction of cyclopentene with Br₂/CCl₄?

Which compound does not give two stereoisomers when reacted with Cl₂/CCl₄?

Select the stereoselective reagents from the following list. HCl H⁺/H₂O Br₂ BH₃ H₂

Which is the product of the reaction of 1-methylcyclohexene with H₂O/H₂SO₄?

Which set of reagents will produce a electrophilic addition to the pi bond of an alkene?? i. H₂O/H₂SO₄ II. Br₂/CCl₄ III. HBr IV. H₂/Pt

Which point on the energy diagram represents the intermediate?

Which statement does not describe a transition state?

But-1-yn-1-ylcyclohexane reacts with molecular hydrogen under pressure in the presence of a Lindlar catalyst. What reaction product is formed?

Which is the major product from acid catalyzed hydration of 2-methyl-2-pentene?

Quiz 1: Covalent Bonding and Shapes of Molecules

Arrange these carbocations in order of increasing stability (least to most) .

Which reagents react with an alkene by anti addition? i. Cl2 II. Br2 III. H2/Pt IV. BH3, followed by H2O2/NaOH/H2O

Which are the major products from the reaction of 1,2-dimethylcyclohexene with H2/Pt?

Compound X has a molecular formula C8H14 and reacts with H2/Pt to give compound Y, C8H16. Which is compound X?

Which compound has the most exothermic (most negative) heat of hydrogenation?

Which reagents react with 2-methyl-1-hexene in a Markovnikov orientation? i. HBr II. H2O/H2SO4 III. Br2 IV. BH3, followed by H2O2/NaOH/H2O

Which energy diagram represents the reaction of HBr with 2-butene?

Which is the major product from the reaction of 1,2-dimethylcyclohexene with Br2?

Which reagents react with an alkene by syn addition? i. Cl2 II. Br2 III. H2/Pt IV. BH3, followed by H2O2/NaOH/H2O

The hydroboration and subsequent oxidation of 1-heptene leads to which of the following products?

Ethynylcyclohexane reacts with sodium amide. The product of that reaction then reacts with bromocyclohexane. What is the main product that is formed?

Which is the major product from the reaction of cyclopentene with Br2/CCl4?

Which compound does not give two stereoisomers when reacted with Cl2/CCl4?

Select the stereoselective reagents from the following list. HCl H+/H2O Br2 BH3 H2

Which is the product of the reaction of 1-methylcyclohexene with H2O/H2SO4?

Which set of reagents will produce a electrophilic addition to the pi bond of an alkene?? i. H2O/H2SO4 II. Br2/CCl4 III. HBr IV. H2/Pt

Which point on the energy diagram represents the intermediate?

Which statement does not describe a transition state?

But-1-yn-1-ylcyclohexane reacts with molecular hydrogen under pressure in the presence of a Lindlar catalyst. What reaction product is formed?

Which is the major product from acid catalyzed hydration of 2-methyl-2-pentene?

Which reagents react with an alkene by anti addition? i. Cl₂ II. Br₂ III. H₂/Pt IV. BH₃, followed by H₂O₂/NaOH/H₂O

Which are the major products from the reaction of 1,2-dimethylcyclohexene with H₂/Pt?

Compound X has a molecular formula C₈H₁₄ and reacts with H₂/Pt to give compound Y, C₈H₁₆. Which is compound X?

Which reagents react with 2-methyl-1-hexene in a Markovnikov orientation? i. HBr II. H₂O/H₂SO₄ III. Br₂ IV. BH₃, followed by H₂O₂/NaOH/H₂O

Which is the major product from the reaction of 1,2-dimethylcyclohexene with Br₂?

Which reagents react with an alkene by syn addition? i. Cl₂ II. Br₂ III. H₂/Pt IV. BH₃, followed by H₂O₂/NaOH/H₂O

Which is the major product from the reaction of cyclopentene with Br₂/CCl₄?

Which compound does not give two stereoisomers when reacted with Cl₂/CCl₄?

Select the stereoselective reagents from the following list. HCl H⁺/H₂O Br₂ BH₃ H₂

Which is the product of the reaction of 1-methylcyclohexene with H₂O/H₂SO₄?

Which set of reagents will produce a electrophilic addition to the pi bond of an alkene?? i. H₂O/H₂SO₄ II. Br₂/CCl₄ III. HBr IV. H₂/Pt