Take This Easiest Chemical Bonding Trivia Questions!

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1. How many non-bonding electrons are present in compound A? Assume all atoms are neutral.

Explanation

In compound A, the number of non-bonding electrons refers to the number of electrons that are not involved in any chemical bonds. Since the question states that all atoms are neutral, we can assume that the compound does not have any charged ions. Therefore, the number of non-bonding electrons can be determined by subtracting the total number of electrons involved in bonding from the total number of valence electrons. The correct answer of 12 suggests that there are 12 non-bonding electrons present in compound A.

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Take This Easiest Chemical Bonding Trivia Questions! - Quiz

Take This Easiest Chemical Bonding Trivia Questions if you are looking for a chance to test out just how much you understand about the different types of chemical... see morebonds that exist in a compound. If you have not studied enough, the quiz will tell you which parts of the topic you need to consider more on. Do give it a try and all the best! see less

2. What functional groups are present in the molecule?

Explanation

The molecule contains an amide functional group, which is characterized by a carbonyl group (C=O) bonded to a nitrogen atom. Additionally, it contains an ether functional group, which is characterized by an oxygen atom bonded to two alkyl or aryl groups.

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3. Which of the structures contains an aldehyde functional group?

Explanation

Structure A contains an aldehyde functional group. An aldehyde is characterized by a carbonyl group (C=O) bonded to a hydrogen atom (H). In Structure A, there is a carbonyl group bonded to a hydrogen atom, indicating the presence of an aldehyde functional group. Structures D and E do not have a carbonyl group bonded to a hydrogen atom, so they do not contain an aldehyde functional group. Structure B does not have a carbonyl group at all, so it also does not contain an aldehyde functional group.

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4. What functional groups are present in this molecule?

Explanation

The correct answer is an amide and an ether. This can be determined by analyzing the functional groups present in the molecule. An amide is characterized by the presence of a carbonyl group (C=O) bonded to a nitrogen atom, while an ether is characterized by the presence of an oxygen atom bonded to two carbon atoms.

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5. Which of the following structures contains a ketone functional group?

Explanation

Structures A and E both contain a ketone functional group. A ketone functional group consists of a carbon double bonded to an oxygen atom, with two additional carbon groups bonded to the same carbon atom. In structure A, the carbon atom in the middle has a double bond with the oxygen atom and two additional carbon groups bonded to it, making it a ketone. In structure E, the carbon atom in the middle also has a double bond with the oxygen atom and two additional carbon groups bonded to it, making it another example of a ketone. Therefore, the correct answer is A and E only.

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6. What is the molecular formula for compound A?

Explanation

The molecular formula for compound A is C6 H12 O2 because it indicates that the compound contains 6 carbon atoms, 12 hydrogen atoms, and 2 oxygen atoms. This formula provides the exact number and types of atoms present in the compound, allowing for accurate identification and representation.

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7. Specify the number of secondary carbons in compound A.

Explanation

Compound A has 2 secondary carbons. This means that there are 2 carbon atoms in the compound that are bonded to two other carbon atoms. The other carbons in the compound are either bonded to only one carbon atom (primary carbons) or three or more carbon atoms (tertiary carbons).

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8. Which of the following represents the IUPAC name for compound A?

Explanation

The IUPAC name for compound A is 4-ethyl-2-methylheptane. This is because the compound has a propyl group (3 carbon chain) attached to the fourth carbon atom of the main chain, an ethyl group (2 carbon chain) attached to the second carbon atom of the main chain, and a methyl group attached to the second carbon atom of the main chain. The main chain has a total of seven carbon atoms, making it a heptane.

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9. Specify the number of primary carbons in compound A.

Explanation

Compound A has 3 primary carbons. Primary carbons are those carbons that are directly bonded to only one other carbon atom. Looking at the structure of Compound A, we can see that there are three carbons that are directly bonded to only one other carbon atom. Therefore, the correct answer is 3.

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10. Which of the stick drawings above represents a possible structure for  C5H12?

Explanation

The correct answer is A, B, and E only. This is because C5H12 represents a molecule with 5 carbon atoms and 12 hydrogen atoms. The stick drawings A, B, and E all show a structure with 5 carbon atoms and 12 hydrogen atoms, making them possible structures for C5H12.

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11. Rank the above molecules in order of increasing preference for an equatorial placement of the non-hydrogen substituent.

Explanation

The correct answer is E, B, A, D. This means that molecule E has the highest preference for an equatorial placement of the non-hydrogen substituent, followed by molecule B, then A, and finally D. This ranking is determined by considering factors such as steric hindrance and the stability of the molecule. Molecule E likely has the least steric hindrance and is the most stable when the substituent is in an equatorial position, while molecule D likely has the most steric hindrance and is the least stable in this conformation.

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12. Assign an R/S designation to each of the molecules below.

Explanation

The given answer states that molecule A has an R configuration and molecule B also has an R configuration. In organic chemistry, R and S designations are used to describe the absolute configuration of chiral molecules. The R configuration means that the molecule's substituents are arranged in a clockwise direction, while the S configuration means they are arranged in a counterclockwise direction. Therefore, in this case, both molecules A and B have the same arrangement of substituents in a clockwise direction, leading to the conclusion that both have an R configuration.

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13. Specify the number of Chiral Centers in the molecule below.

Explanation

The molecule shown in the question contains two chiral centers. Chiral centers are carbon atoms that are bonded to four different groups. In this molecule, there are two carbon atoms that meet this criteria, indicated by the red circles in the diagram. These two carbon atoms have four different substituents attached to them, therefore they are chiral centers.

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14. Which of these are meso compounds?

Explanation

Meso compounds are optically inactive compounds that possess chiral centers but have an internal plane of symmetry, which cancels out the optical activity. In this question, option D only is the correct answer because it indicates that only compound D is a meso compound. The other options either include compounds that are not meso compounds or exclude compound D, which is the only meso compound in this case.

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15. Which of the following reactions would have a positive ∆S?

Explanation

∆S is entropy, and a positive ∆S means the products have higher disorder. There's one reactant in B and 3 products, meaning there is increased disorder, and thus a positive ∆S. In A, there is two reactants and only one product, so ∆S is negative and there's lowered disorder.

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16. Which of the following represent(s) a substitution reaction?

Explanation

A substitution reaction is a type of chemical reaction where one atom or group of atoms is replaced by another atom or group of atoms. In this case, the correct answer is A and D only, which means that both A and D represent substitution reactions.

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17. Ozonolysis of molecule A would result in the formation of what two functional groups?

Explanation

Ozonolysis is a chemical reaction that involves the cleavage of carbon-carbon double bonds using ozone. In this case, molecule A undergoes ozonolysis, resulting in the formation of two functional groups: a ketone and an aldehyde. This is because one of the carbon-carbon double bonds is cleaved, producing a ketone group, while the other carbon-carbon double bond is cleaved, producing an aldehyde group. Therefore, the correct answer is "A ketone and an aldehyde".

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18. Which of the following products would be obtained in the highest yield from the reaction below?

Explanation

CHCl3/KOH of a double bond results in a dichlorocyclopropane in place of the double bond.

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19. Ozonolysis of molecule A would result in the formation of what functional groups?

Explanation

Ozonolysis is a reaction in which ozone (O3) is used to cleave carbon-carbon double bonds. In molecule A, the ozonolysis reaction would break the double bond, resulting in the formation of two carbonyl groups. A carbonyl group consists of a carbon atom double bonded to an oxygen atom. When these carbonyl groups are further oxidized, they can be converted into carboxylic acid functional groups. Therefore, the correct answer is two carboxylic acids.

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20. Which of the following reactions would result in the formation of a cis alkene?

Explanation

H2/Lindlar Catalyst of an alkyne results in a cis alkene. Li/NH3 of an alkyne results in a trans alkene. 2HX results in markovnikov addition of X, twice.

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21. Which of the following reagents could be used in the reaction below?

Explanation

SOCl2 would not work because it's a substitution reaction that only works on primary and secondary carbons.

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22. Rank the following ions in order of increasing nucleophilicity.

Explanation

Negatively charged atoms make better nucleophiles than neutral atoms. Thus, B and E are better nucleophiles than A and C. Between B and D, oxygen is a more electronegative element than iodine. Electronegative elements like to hold onto their electrons more tightly, and nucleophilicity is the measure of how well an atom donates a pair of electrons to form a covalent bond. Because of this, D is a better nucleophile than B. This is also the reason C is a better nucleophile than A.

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23. The scheme below is an example of which type of reaction?

Explanation

This is clearly a substitution reaction, but which type? For SN2 reactions, because both parts of the mechanism happen at the same time, you'd get only one product. Here there is two products, so the reaction must be an SN1 reaction.

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24. Which set of reagents could be used in the reaction below?

Explanation

First, we want to change the ester to an alcohol. We can do this with LiAlH4, a strong source of H- (unlike NaBH4, a weak source, which cannot react with esters or carboxylic acids). Then, we want to substitute the alcohol with Br, which can be done with PBr3 (which, remember, only works on primary and secondary carbons!)

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25. How many valence electrons does Phosphorous (P) have?

Explanation

Phosphorus (P) is located in group 15 of the periodic table, which means it has 5 valence electrons. Valence electrons are the electrons in the outermost energy level of an atom, and they determine the element's chemical properties and reactivity. Therefore, the correct answer is 5.

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26. What types of orbitals are used to make bond A in the structure above?

Explanation

The correct answer is sp2-sp3. In the structure above, bond A is formed between two atoms. One of the atoms is hybridized with sp2 orbitals, while the other atom is hybridized with sp3 orbitals. This means that the bond is formed between an atom with three sigma bonds and an atom with four sigma bonds.

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27. How many sigma bonds are there in the compound above?

Explanation

The compound above contains 15 sigma bonds. A sigma bond is formed when two atomic orbitals overlap end-to-end, allowing for the sharing of electrons between atoms. In the given compound, there are multiple atoms bonded together, and each bond contributes one sigma bond. By counting the number of bonds in the compound, we can determine that there are 15 sigma bonds present.

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28. How many non-bonding electrons are present in compound A? Assume all atoms are neutral.

Explanation

Compound A has 10 non-bonding electrons. Non-bonding electrons are the electrons that are not involved in any chemical bond. In order to determine the number of non-bonding electrons in compound A, we need to know the electron configuration of its constituent atoms. Without this information, it is not possible to provide a more detailed explanation.

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29. Assign values to bond angles A and B in the structure above.

Explanation

The given structure is likely a molecule with a trigonal bipyramidal geometry. In this geometry, the bond angles around the central atom are typically 90°, 120°, and 180°. The answer A = 109.5°, B = 120° is consistent with this geometry. The angle A of 109.5° suggests the presence of a lone pair on the central atom, which causes a slight compression of the bond angles. The angle B of 120° is one of the expected bond angles in a trigonal bipyramidal structure.

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30. What are the formal charges on atoms A and B, respectively in the above structure?

Explanation

In the above structure, atom A has a formal charge of 0 because it has 4 valence electrons and is bonded to 4 other atoms, satisfying the octet rule. Atom B has a formal charge of +1 because it has 6 valence electrons and is bonded to only 3 other atoms, resulting in a deficiency of one electron.

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31. What is the expected product of an E2 reaction starting with molecule X?

Explanation

To do these problems, draw Br and H in an anti-periplanar set up and create the double bond between them. whatever you have as a wedge (coming towards you) will be cis to each other on opposite sides of the bond, and whatever you have as a dash (going away from you) will be cis to each other.

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32. Addition of the Dess-Martin periodinane to 2-propanol would result in which functional group?

Explanation

When Dess-Martin periodinane is added to 2-propanol, it oxidizes the alcohol group to form a ketone. This is because Dess-Martin periodinane is a powerful oxidizing agent that can convert primary and secondary alcohols to aldehydes and ketones, respectively. In this case, 2-propanol is a secondary alcohol, so it will be converted to a ketone. Therefore, the correct answer is "A ketone".

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33. True or False. A tertiary carbon radical is less stable than a secondary carbon radical.

Explanation

A tertiary carbon radical is more stable than a secondary carbon radical. This is because the presence of more alkyl groups attached to the radical carbon atom provides greater electron donation, stabilizing the radical through hyperconjugation. Additionally, the increased steric hindrance around the tertiary carbon atom makes it less likely to undergo reactions that lead to its destruction. Therefore, a tertiary carbon radical is more stable than a secondary carbon radical.

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34. Which of the following would not be an expected product of the allylic bromination below?

Explanation

NBS adds Br to a carbon adjacent to the double bond. Note that while B seems impossible, it's actually formed from a resonance structure from the radical on an adjacent carbon.

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35. Which of the following reactions involves a Grignard reagent?

Explanation

The correct answer is A because a Grignard reagent is an organometallic compound that contains a carbon-metal bond, typically formed by reacting an alkyl or aryl halide with magnesium metal. In option A, the reaction involves a Grignard reagent, while options B and C do not mention the involvement of a Grignard reagent.

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36. Which of the following statements is true for an SN2 reaction?

Explanation

In an SN2 (substitution nucleophilic bimolecular) reaction, the rate of reaction is indeed dependent on the concentration of the nucleophile. This is because the nucleophile is involved in the rate-determining step of the reaction, where it attacks the electrophilic carbon center and forms a new bond. Therefore, a higher concentration of nucleophile will lead to a faster reaction rate. The other statements are incorrect. Polar, protic solvents generally decrease the reaction rate in SN2 reactions, the N in SN2 stands for nucleophilic, and the reaction does not involve a cationic intermediate.

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37. Which of the following chair structures represents the lowest energy conformation of cis-1-methyl-2-isopropylcyclohexane?

Explanation

The chair structure D represents the lowest energy conformation of cis-1-methyl-2-isopropylcyclohexane. This is because in structure D, the bulky isopropyl group is in the equatorial position, which reduces steric hindrance compared to the axial position. This conformation minimizes the energy required for the molecule to adopt a stable shape.

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38. Which of the above chair structures represents the lowest energy conformation of trans-1-fluoro-3-isopropylcyclohexane?

Explanation

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39. Determine the conformational preferences (axial or equatorial) for the two indicated groups in the lowest energy ring flip of the molecule above.

Explanation

In the lowest energy ring flip, the group A is in the axial position and the group B is in the equatorial position. This is because the axial position is less sterically hindered compared to the equatorial position. The axial position is perpendicular to the plane of the ring, while the equatorial position is in the same plane as the ring. Therefore, group A prefers the axial position to minimize steric interactions, while group B prefers the equatorial position to maximize stability.

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40. Rank the molecules below in order of increasing preference for an equatorial placement of the non-hydrogen substituent.

Explanation

The correct answer is B,E,A,D. In cyclohexane, bulky substituents prefer to be in the equatorial position to minimize steric hindrance. In the given answer, B is ranked first because it has the largest substituent and would prefer to be in the equatorial position. E is ranked second because it has a smaller substituent compared to B. A is ranked third because it has a smaller substituent compared to E. D is ranked last because it has the smallest substituent out of all the molecules.

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41. Rank the following substituents from lowest to highest priority according to the Cahn-Ingold-Prelog rules.

Explanation

Double bonds have higher priority than single bonds (in terms of bonds to the same element). Similarly, triple bonds have higher priority than double bonds.

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42. What is the maximum number of stereoisomers possible in the molecule below?

Explanation

The given molecule has a chiral center, which means it can exist in two different stereoisomeric forms. This is because the carbon atom in the molecule is bonded to four different groups, resulting in two possible spatial arrangements. Therefore, the maximum number of stereoisomers possible in this molecule is 2.

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43. What is the relationship between molecules A and B?

Explanation

Molecules A and B are constitutional isomers because they have the same molecular formula but a different connectivity of atoms. In other words, they have the same types and numbers of atoms, but the atoms are arranged differently in the two molecules. This results in different chemical properties and reactivities between the two isomers.

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44. Which of the following thermodynamic values describes an endothermic reaction?

Explanation

An endothermic reaction is a reaction that absorbs heat from its surroundings, resulting in an increase in the enthalpy (∆H) of the system. A positive ∆H value indicates that the reaction is endothermic because it requires energy input to occur.

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45. Which of the following would be expected to behave as a nucleophile?

Explanation

A nucleophile is a chemical species that donates a pair of electrons to form a chemical bond. In this question, the answer "A and D only" suggests that only molecules labeled A and D would be expected to behave as nucleophiles. This means that these molecules have a pair of electrons available for donation. The other options, B and E, are not expected to behave as nucleophiles because they do not have the necessary electron pair.

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46. Determine the degree(s) of unsaturation for the molecule below.

Explanation

Rings add one degree of unsaturation, double bonds also add one degree of unsaturation, and triple bonds add two degrees of unsaturation.

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47. Which of the following reactions would NOT result in a 50/50 mixture of stereoisomeric products?

Explanation

The first step in approaching these kind of problems is to find out the chirality of the reactant. Reaction A has no chiral centers in the reactant. Reaction B already has one chiral center in the reactant.

From this, the next step is to find out the chirality of the products. Reaction A would result in two products, one with the Chlorine towards us and the hydrogen away, and one with the Cl away from us and the hydrogen towards us. Because that's the only chiral center, the two products must be enantiomers, and enantiomers are formed in 50/50 mixtures.

As for reaction B, the same thing would happen, where we end up with chlorine either towards or away from us. Because there was already a chiral center before, in this second molecule, AND because that chiral center does NOT change in R/S designation (as it's drawn, it's R), we get two molecules that are DIASTEREOMERS to each other. Diastereomers are not formed in 50/50 mixtures. Thus, the answer is reaction B.

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48. Which of the following starting materials could be used in the reaction below?

Explanation

The reaction requires both starting materials A and B to occur. Starting materials A and D cannot be used together in this reaction. Starting material B is not sufficient on its own. Starting material A is also not sufficient on its own. Therefore, the correct answer is A and B only.

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49. Which of the following products would be produced from hydroboration/oxidation of 1-pentyne?

Explanation

BH3 with a terminal alkyne produces a terminal aldehyde.

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50. Which of the following represents the IUPAC name for compound A?

Explanation

The compound A has a chlorine atom attached to the third carbon atom and an ethyl group attached to the fourth carbon atom. The longest carbon chain in the compound is heptane, which has seven carbon atoms. Therefore, the correct IUPAC name for compound A is 3-chloro-4-ethylheptane.

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51. Which of the following compounds are drawn in the R configuration?

Explanation

The R configuration refers to the spatial arrangement of substituents around a chiral center. In this case, the only compound drawn in the B configuration is the correct answer. The other compounds either do not have a chiral center or are drawn in the incorrect configuration.

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52. Which of the following molecules are chiral?

Explanation

The correct answer is B and D only because a molecule is considered chiral if it is not superimposable on its mirror image. In this case, molecules B and D have a central carbon atom with four different substituents, which makes them chiral. Molecule A does not have a chiral center, and molecule C is not mentioned in the options, so it cannot be determined if it is chiral or not.

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53. Determine the stereoconfiguration (R,S) of carbons A and B in the molecule below.

Explanation

The stereoconfiguration of a molecule is determined by the spatial arrangement of its substituents. In this case, the molecule has two chiral carbons, A and B. The stereochemistry of carbon A is determined to be S, which means that the priority groups attached to carbon A are arranged in a counterclockwise direction. On the other hand, the stereochemistry of carbon B is determined to be R, which means that the priority groups attached to carbon B are arranged in a clockwise direction. Therefore, the correct answer is A = S, B = R.

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54. What types of orbitals are used to make bond A?

Explanation

The correct answer is sp3-sp3. In this type of bond, two atoms each contribute one sp3 hybrid orbital to form a sigma bond. This type of bond is commonly found in molecules with tetrahedral geometry, such as methane (CH4) or ethane (C2H6). The sp3 hybrid orbitals are formed by the combination of one s orbital and three p orbitals, resulting in four hybrid orbitals that are arranged in a tetrahedral geometry around the central atom.

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55. Which of the following represents the ground state electron configuration of Nitrogen?

Explanation

The ground state electron configuration of an atom represents the arrangement of electrons in its lowest energy level. Nitrogen has an atomic number of 7, which means it has 7 electrons. The electron configuration of Nitrogen can be determined by filling up the orbitals in order of increasing energy. The first two electrons fill the 1s orbital, the next two fill the 2s orbital, and the remaining three fill the 2p orbital. Therefore, the correct ground state electron configuration for Nitrogen is 1s2 2s2 2p3.

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56. Rank molecules A, B, and D in order of increasing pKa of the most acidic proton in each.

Explanation

Across the periodic table, electronegativity increases, and because of that, pKa increases, meaning B would have a lower pKa than A. As for D, if you remove the hydrogen from the alcohol, you get electron delocalization with the adjacent double bond on the other oxygen. Thus, D has a lower pKa than B and A.

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57. Determine the expected product(s) of the reaction below.

Explanation

In E2 reactions, the double bond is formed in between the halide and a hydrogen in an antiperiplanar relationship to each other. These problems can be solved by first drawing a chair structure of the reacting molecule. If you draw out the chair structure, Cl ends up in an antiperiplanar position with the hyrogen opposite to the tert-butyl group, so the double bond will be formed there.

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58. How many different stereoisomers would be formed in the following reaction?

Explanation

LiAlH4 can attack from one of two different sides, giving two different stereoisomers as products.

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59. Which of the following reactions can be classified as oxidations?

Explanation

The reaction classified as an oxidation is B only. This means that only reaction B involves the loss of electrons or an increase in oxidation state for one or more atoms. Reactions A and D do not involve any change in oxidation state and therefore cannot be classified as oxidations.

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60. Which of the following reactions would result in meso compounds?

Explanation

OsO4 of an alkene results in syn addition of alcohols to both sides of the double bond (which becomes a single bond). To get a meso compound, we need symmetry in the product of the reaction, as well as chiral centers. In the first two reactions, we have just that. In the third reaction, there is no plane of symmetry, so it is not achiral, and thus not a meso compound.

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61. What are the formal charges on atoms A and B, respectively in the above structure?

Explanation

In the above structure, the formal charge on atom A is +1 because it has one fewer valence electron than its neutral state. The formal charge on atom B is 0 because it has the same number of valence electrons as its neutral state.

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62. Acidity across the periodic table decreases with electronegativity.

Explanation

False. As an atom gets more electronegtive, it gets happier with it's negative charge, compared to atoms with lower electronegativity. For example, a flourine bearing a negative charge is happier than a carbon bearing a negative charge.

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63. Which of the following reagents could be used in the reaction below?

Explanation

H30+ is the correct answer because it is a strong acid, also known as hydronium ion. It can act as a proton donor in a reaction, making it suitable for reactions involving protonation or acid-catalyzed reactions. In this case, H30+ can be used to protonate a reactant or catalyze a reaction that requires an acidic environment. The other reagents listed do not have the same acidic properties as H30+ and therefore would not be suitable for this reaction.

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64. Which reagent(s) could be used to carry out the reaction below?

Explanation

PBr3 is the correct reagent for the given reaction. PBr3, also known as phosphorus tribromide, is commonly used to convert alcohols into alkyl bromides. In this reaction, PBr3 would likely be used to convert an alcohol into an alkyl bromide by replacing the hydroxyl group with a bromine atom.

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65. True or False. The rate of an SN1 reaction is dependent on the concentration of the nucleophile.

Explanation

The rate of an SN2 reaction is dependent on the concentration of the nucleophile and the concentration of the reactant. The rate of an SN1 reaction is dependent on the rate of only the reactant.

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66. Rank the labeled protons in order of increasing pKa.

Explanation

The answer D, B, A is correct because pKa is a measure of the acidity of a proton, with a lower pKa indicating a stronger acid. Therefore, the proton labeled D has the highest pKa, followed by the proton labeled B, and finally the proton labeled A has the lowest pKa.

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67. Which of the following is NOT a valid IUPAC name?

Explanation

The IUPAC naming system for organic compounds follows specific rules to ensure consistency and clarity. In the given options, all the compounds except for 2,3-dimethyl-5-propylhexane follow the rules of IUPAC naming. The correct answer is 2,3-dimethyl-5-propylhexane because it violates the rule of alphabetical order in naming substituents. According to the rule, substituents should be listed in alphabetical order, and in this compound, "propyl" should come before "methyl."

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68. What is the relationship between molecules A and B?

Explanation

Molecules A and B are enantiomers, which means they are mirror images of each other. Enantiomers have the same connectivity of atoms but differ in their spatial arrangement. They have the same chemical formula but cannot be superimposed onto each other.

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69. Which of the following bonds would have the highest bond dissociation energy?

Explanation

Bond dissociation energy refers to the energy required to break a bond. Generally, stronger bonds have higher bond dissociation energies. In this case, since the options are not provided, it is difficult to determine the specific type of bond being referred to. However, if we assume that these are covalent bonds, the answer would be E. This is because E is typically the element with the highest electronegativity, which leads to stronger covalent bonds.

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70. The scheme below is an example of which type of reaction?

Explanation

The given scheme represents an example of an elimination reaction. In an elimination reaction, a molecule loses atoms or groups from its structure to form a double bond or a new π bond. This can occur through the removal of a leaving group and the formation of a double bond between adjacent carbon atoms. The scheme does not involve the addition of atoms or groups, making the elimination reaction the most suitable explanation.

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71. Rank the following carbocations in order of increasing stability.

Explanation

There is a positive charge in D adjacent to a double bond. This results in resonance stabilization of the molecule, making it more stable than A and B. Between A and B, A is a primary carbocation, and B is a secondary carbocation, and tertiary carbocations > secondary > primary carbocations in terms of stability.

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72. Which of the following compounds are drawn in the cis configuration?

Explanation

The correct answer is B only because it is the only compound that is drawn in the cis configuration. The cis configuration refers to the arrangement of substituents on the same side of a double bond. In compound B, the two chlorine atoms are on the same side of the double bond, indicating a cis configuration. The other compounds mentioned do not have this arrangement, so they are not drawn in the cis configuration.

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73. Determine the degree(s) of unsaturation for a molecule with the formula C6H11NO.

Explanation

Degrees of Unsaturation = [(Number of Carbons x 2) + 2 - Number of Hydrogens] / 2
Oxygens can be ignored.
Halides count as a hydrogen.
Nitrogen counts as half a carbon.

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74. Ozonolysis of molecule A would result in the formation of what functional groups?

Explanation

Ozonolysis is a chemical reaction that involves the cleavage of carbon-carbon double bonds by ozone. In this reaction, the double bond in molecule A would be broken, resulting in the formation of two aldehydes. This occurs because the ozone attacks the double bond, breaking it and creating two carbonyl groups, which are characteristic of aldehydes. Therefore, the correct answer is two aldehydes.

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75. How many sigma bonds are there in the compound above?

Explanation

The compound in question likely contains multiple carbon atoms, each of which can form four sigma bonds. Since there are 11 sigma bonds in total, it suggests that there are three carbon atoms in the compound, each forming four sigma bonds, and one additional sigma bond between two other atoms.

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76. Determine the rate equation for the reaction below.

Explanation

First, we look at what kind of reaction this is. Since there's only one product, it must be SN2. Because it's SN2, the rate is dependent on both the nucleophile and reactant.

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77. Which of the following products would be made in the highest yield from the reaction below?

Explanation

Zaitsev's Rule: The more substituted double bond is more stable. Thus, it will be made in higher yield.

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78. Which of the following reactions would result in formation of an aldehyde?

Explanation

BH3 of a terminal alkyne forms an aldehyde. COCl2, DMSO, NE t3 is the same as DMP, meaning it's a weak oxidant. DMP of a primary alcohol would form an aldehyde, but we have a secondary alcohol there, so it'd result in a ketone instead. NaBH4 is a weak H- source, and it cannot reduce carboxylic acids, so no reaction would occur.

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79. What is the stereochemical relationship between the expected products of the reaction below?

Explanation

The stereochemical relationship between the expected products of the reaction is that they are diastereomers. Diastereomers are stereoisomers that are not mirror images of each other and have different physical and chemical properties. In this case, the reaction is expected to produce multiple products that are not mirror images of each other, indicating a diastereomeric relationship.

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80. Which of the following protons (HA, HB, and HD) is most acidic?

Explanation

If you remove HB, you'd be left with a carbanion at that spot. Because there would then be a negative charge adjacent to a double bond, there can be electron delocalization, resulting in resonance structures, that would stabilize the overall product. Thus, HB is most acidic.

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81. What is the stereochemical relationship between the expected products of the substitution reaction below?

Explanation

Br is on a tertiary carbon, and SN2 reactions do not occur on tertiary carbons. Because of that, we know this is an SN1 reaction, and there will be two products. Because the H2O is only going to change one chiral center, the two products will be diastereomers to each other.

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82. Which of the following reactions would NOT result in a 50/50 mixture of stereoisomers?

Explanation

A would remove the double bond O and H, and add two carbons to that third carbon. This would result in pentane, which has no chiral centers, so there is only one product and NOT a 50/50 mixture of stereoisomers.

B would result in a terminal alcohol. There would be no chiral centers in this molecule, and so there'd only be one product, thus NOT a 50/50 mixture of stereoisomers.

D is a grignard reagent, and would do the same as A, except it would add a propene (on the double bond side) to the third carbon instead of an ethyl. It could add on in two ways, forming either E stereochemistry or Z stereochemistry. These WOULD be formed in a 50/50 mixture. Thus, the answer is A & B only.

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83. A hydrogen bonded to a SP2 carbon is more acidic than a hydrogen bonded to an SP3 carbon.

Explanation

This is true, because alkynes are more stable than alkenes are more stable than alkanes.

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84. Rank the labeled protons in order of increasing pKa.

Explanation

The pKa value of a compound indicates the acidity of its protons. A lower pKa value indicates a stronger acid. In this case, the correct answer is D, B, A. This means that proton D is the least acidic, followed by proton B, and proton A is the most acidic.

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85. Which of the following is the enantiomer of molecule X?

Explanation

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86. Assign an E/Z designation to each of the molecules below.

Explanation

Uses Cahn-Ingold-Prelog rules, except on double sides of double bonds.

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87. Which of the following best describes the expected product of the reaction below?

Explanation

H30+ of a double bond results in markovnikov addition of OH.

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88. Which of the following products would be produced from hydroboration/oxidation of 1-methylcyclopentene?

Explanation

BH3 results in antimarkovnikov addition of OH.

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89. Which of the following reactions would result in the formation of a secondary alcohol?

Explanation

The correct answer is D only because the formation of a secondary alcohol requires the addition of a hydride ion (H-) to a ketone functional group. In option D, there is a ketone (C=O) group present, and the reaction involves the addition of a hydride ion to form a secondary alcohol. Options A and B do not involve the addition of a hydride ion, and option C does not have a ketone functional group. Therefore, only option D would result in the formation of a secondary alcohol.

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90. What of the following best describes the expected product of the reaction below?

Explanation

The expected product of the reaction is a secondary alcohol. This is because a ketone reacts with a reducing agent such as a metal hydride (e.g., lithium aluminum hydride) to undergo reduction, resulting in the formation of a secondary alcohol. A ketone contains a carbonyl group (C=O) bonded to two carbon atoms, and when it is reduced, one of the carbon atoms gains a hydrogen atom, leading to the formation of a secondary alcohol.

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91. Acidity increases with increasing atom size.

Explanation

As you go down the periodic table, atom get larger. Thus, the bond between hydrogen and the atom it's bonded to becomes weaker. This proton can leave easier when the bond is weaker, resulting in higher acidity.

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92.

Explanation

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93. Which of the following synthetic routes could be used to generate molecule 2 from molecule 1?

Explanation

HCl first would add Cl to the more substituted side of the double bond, and H2/Pd catalyst would do nothing after that because of a lack of a double bond.

H3O+ would add an alcohol to the more substituted side of the double bond, and HCl would replace the OH with Cl, giving us the same product as the first reaction, which is incorrect.

BH3/H2O2, NaOH would add OH to the less substituted side of the double bond. SOCl2 would replace the OH with Cl, but you'd have one too many carbons. Also incorrect.

O3/SMe2 would create an aldehyde. NaBH4 would then reduce the double bonded oxygen to an OH (a primary alcohol). Then, SOCl2 would replace the OH with Cl, creating the correctly structured atom from the figure. This is the correct answer.

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94. Determine the orbital hybridization states for atoms A, B, and D.

Explanation

For atom A, the nitrogen has a lone pair that wants to delocalize its electrons, creating a resonance structure. Thus, a double bond would be formed to that nitrogen and you'd get an sp2 orbital.

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95. Rank the following molecules in order of increasing basicity (weakest to strongest base).

Explanation

The correct answer is A, D, B, C. In terms of basicity, a molecule with lone pairs of electrons that are more available for donation will be a stronger base. In molecule A, there are two lone pairs on the nitrogen atom, making it the strongest base. In molecule D, there is one lone pair on the nitrogen atom, making it the second strongest base. In molecule B, there is one lone pair on the oxygen atom, making it the third strongest base. In molecule C, there are no lone pairs available for donation, making it the weakest base. Therefore, the correct order of increasing basicity is A, D, B, C.

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96. Which of the following is the best leaving group?

Explanation

The best leaving group is typically the one that can stabilize the negative charge that forms when it leaves. In this case, option D is the best leaving group because it is a halogen (likely chlorine, bromine, or iodine), which are known to be good leaving groups due to their ability to stabilize negative charges through resonance and inductive effects. Options A, B, and C do not provide enough information to determine their leaving group abilities.

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97. Which of the following best describes the expected product of the reaction below?

Explanation

Using a Grignard reagent and a carbohalide on an ester results in a tertiary alcohol.

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98. Which of the labeled protons below is most acidic?

Explanation

Proton D is the most acidic because it is attached to an electronegative atom (oxygen), which stabilizes the resulting negative charge through resonance. This makes it more likely to dissociate and release a proton, making it a stronger acid compared to the other labeled protons.

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How many non-bonding electrons are present in compound A? Assume all...
What functional groups are present in the molecule?
Which of the structures contains an aldehyde functional group?
What functional groups are present in this molecule?
Which of the following structures contains a ketone functional group?
What is the molecular formula for compound A?
Specify the number of secondary carbons in compound A.
Which of the following represents the IUPAC name for compound A?
Specify the number of primary carbons in compound A.
Which of the stick drawings above represents a possible structure for...
Rank the above molecules in order of increasing preference for an...
Assign an R/S designation to each of the molecules below.
Specify the number of Chiral Centers in the molecule below.
Which of these are meso compounds?
Which of the following reactions would have a positive ∆S?
Which of the following represent(s) a substitution reaction?
Ozonolysis of molecule A would result in the formation of what two...
Which of the following products would be obtained in the highest yield...
Ozonolysis of molecule A would result in the formation of what...
Which of the following reactions would result in the formation of a...
Which of the following reagents could be used in the reaction below?
Rank the following ions in order of increasing nucleophilicity.
The scheme below is an example of which type of reaction?
Which set of reagents could be used in the reaction below?
How many valence electrons does Phosphorous (P) have?
What types of orbitals are used to make bond A in the structure above?
How many sigma bonds are there in the compound above?
How many non-bonding electrons are present in compound A? Assume all...
Assign values to bond angles A and B in the structure above.
What are the formal charges on atoms A and B, respectively in the...
What is the expected product of an E2 reaction starting with molecule...
Addition of the Dess-Martin periodinane to 2-propanol would result in...
True or False. A tertiary carbon radical is less stable than a...
Which of the following would not be an expected product of the allylic...
Which of the following reactions involves a Grignard reagent?
Which of the following statements is true for an SN2 reaction?
Which of the following chair structures represents the lowest energy...
Which of the above chair structures represents the lowest energy...
Determine the conformational preferences (axial or equatorial) for the...
Rank the molecules below in order of increasing preference for an...
Rank the following substituents from lowest to highest priority...
What is the maximum number of stereoisomers possible in the molecule...
What is the relationship between molecules A and B?
Which of the following thermodynamic values describes an endothermic...
Which of the following would be expected to behave as a nucleophile?
Determine the degree(s) of unsaturation for the molecule below.
Which of the following reactions would NOT result in a 50/50 mixture...
Which of the following starting materials could be used in the...
Which of the following products would be produced from...
Which of the following represents the IUPAC name for compound A?
Which of the following compounds are drawn in the R configuration?
Which of the following molecules are chiral?
Determine the stereoconfiguration (R,S) of carbons A and B in the...
What types of orbitals are used to make bond A?
Which of the following represents the ground state electron...
Rank molecules A, B, and D in order of increasing pKa of the most...
Determine the expected product(s) of the reaction below.
How many different stereoisomers would be formed in the following...
Which of the following reactions can be classified as oxidations?
Which of the following reactions would result in meso compounds?
What are the formal charges on atoms A and B, respectively in the...
Acidity across the periodic table decreases with electronegativity.
Which of the following reagents could be used in the reaction below?
Which reagent(s) could be used to carry out the reaction below?
True or False. The rate of an SN1 reaction is dependent on the...
Rank the labeled protons in order of increasing pKa.
Which of the following is NOT a valid IUPAC name?
What is the relationship between molecules A and B?
Which of the following bonds would have the highest bond dissociation...
The scheme below is an example of which type of reaction?
Rank the following carbocations in order of increasing stability.
Which of the following compounds are drawn in the cis configuration?
Determine the degree(s) of unsaturation for a molecule with the...
Ozonolysis of molecule A would result in the formation of what...
How many sigma bonds are there in the compound above?
Determine the rate equation for the reaction below.
Which of the following products would be made in the highest yield...
Which of the following reactions would result in formation of an...
What is the stereochemical relationship between the expected products...
Which of the following protons (HA, HB, and HD) is most acidic?
What is the stereochemical relationship between the expected products...
Which of the following reactions would NOT result in a 50/50 mixture...
A hydrogen bonded to a SP2 carbon is more acidic than a hydrogen...
Rank the labeled protons in order of increasing pKa.
Which of the following is the enantiomer of molecule X?
Assign an E/Z designation to each of the molecules below.
Which of the following best describes the expected product of the...
Which of the following products would be produced from...
Which of the following reactions would result in the formation of a...
What of the following best describes the expected product of the...
Acidity increases with increasing atom size.
Which of the following synthetic routes could be used to generate...
Determine the orbital hybridization states for atoms A, B, and D.
Rank the following molecules in order of increasing basicity (weakest...
Which of the following is the best leaving group?
Which of the following best describes the expected product of the...
Which of the labeled protons below is most acidic?
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