CHEM104 Final Exam - Organic Chemistry II | Practice Test / Quiz / MCQs

1. Nucleophilic aromatic substitution (NAS) is very similar to Sn2 substitution of alkanes because:

Inversion of the stereochemistry at the substituted carbon occurs during reaction.In both cases, a highly active nucleophile is the attacking species.Displacement occurs in a single step.It is a process involving an attacking species and a leaving group, although for NAS there is also an intermediate.

2. Even without a topic on polymers, can you pick out which of the following is not true?

Lipids are long-chain alkyl esters (of fatty acids) found in many living organisms.RNA and DNA are polyesters made from inorganic phosporic acid and substituted sugar molecules.The common polymer cellulose is found in virtually all living organisms.Polyester used in clothing and soda bottles is made from terephthalic acid and ethlene glycol (the same chemical used in antifreeze).

3. You try to react 1, 5-cyclooctadione with chlorine using NaH as catalyst.You forget to weigh the NaH and end up using 2 equivalents which gives you a product with no chlorine but different from the starting material: what is it?

The first step gives 2-chloro-1, 5-cyclooctadione but the second NaH reduces off the chlorine to give back the starting material.The first step goes fine to give 2, 6-dichloro-1, 5-cyclooctadione.The second NaH dehydrohalogenates to give a double bond conjugated to each of the ring carbonyls.The NaH reduces both carbonyls to alcohols.The first step works fine, with deprotonation alpha to one carbonyl followed by reaction with chlorine to give the alpha-chloro species.However, the second NaH dehydrochlorinates to give the cyclooctadione with a double bond conjugated to one of the ketones.

4. You unexpectedly are given hundreds of tons of 1, 3-cyclohexadiene.You decide to convert it to benzene by:

carefully adding excess chlorine followed by excess KOH in alcohol.treating with NaOH in water to make the alcohol followed by distillation from concentrated sulfuric acid.first reacting with chlorine gas and UV light followed by KOH in alcohol.heating it in the presence of a hydrogen and a catalyst such as palladium.

5. Amines and acids both have:

basic characters- they make water have a higher pH value when dissolved in it.exchangable hydrogens that can be converted to deuterium with heavy water (D2O).acidic characters- they make water have a lower pH value when dissolved in it.greater volatility than alkanes with the same number of carbons.

6. Which acid derivative and what reaction conditions would give an aryl ketone?

Heating an anhydride with the aromatic in refluxing water containing a strong acid catalyst.Carefully adding an aryl Grignard reagent to a carboxylic acid dissolved in an organic solvent.Slowly adding a carboxylic acid to a mixture of concentrated nitric acid and the aromatic compound.Reaction of an acid chloride with a reasonably activated aromatic using a strong Lewis acid catalyst.

7. Hair and skin are made of the same natural polymer as rhino horns: what is it?

A natural polymer called starch made up of glucose repeat units.A natural polyamide or protein with a unique arrangement intra- and intermolecular hydrogen bonds along the chains.A complex carbohydrate containing both saccharides and amino acids in the polymer repeat units.A complex mixture of inorganic phosphate and cellulose that has extremely strong intermolecular forces holding the chains together.

8. You want to make para-hydroxybenzoic acid, so you decide to do both EAS and NAS as follows:

You react benzoic acid with chlorine and iron catalyst, then treat with concentrated NaOH in water and heat.You first react toluene with hot permanganate to make benzoic acid, then react that with chlorine/iron to make the para-chlorobenzoic acid which you heat with NaOH in water.You react toluene with concentrated NaOH in water at reflux to do NAS formation of the hydroxide, and then oxidize the methyl group with hot permanganate to give the acid.You react para-chlorotoulene with hot KMnO4, isolate the product and then react it with hot methanol and HCl catalyst.The product of this you react with neat NaOH in the melt.

9. A good explanation of aromatic stabilization involves which of the following?

A more even distribution of pi electrons occurs in aromatic molecules.The molecular orbitals that form from a conjugated cyclic array of p-orbitalswith just the right number of electrons in them are substantially lower in energy than for non-conjugated systems.There is no good explanation that we know of, it's just a fact of nature.Rapid resonance of pi electrons spreads the electron density over more atoms.

10. Carboxylic acids have a unique combination of:

a central sp2 hybridized carbon, one sp2 hybridized oxygen and one sp3 hybridized oxygen.an sp2 hybridized carbon that can accept a proton from another acid's sp3 hybridized OH moiety.None of these.basicity and nucleophilicity to substitution reactions.

11. It's possible to make a polymer from a conjugated double bond diene.Pick the right diene below and the polymer that it forms.

1, 2-propadiene (gives a polymer with three carbon backbone).2-methyl-1, 3-butadiene (also called isoprene), gives polyisoprene like the natural rubber used in tires.2, 4-hexadiene (gives a polymer with four carbon backbone and two pendent methyl groups).1, 5-hexadiene (gives a polymer with four carbon backbone and two-carbon pendent group).

12. Please name the diene that is a cyclic six-carbon ring with two double bonds (conjugated).

1, 4-cyclohexadiene.1, 2-cyclohexadiene.1, 3-cyclohexadiene1, 5-cyclohexadiene

13. Trees and cotton are made of what natural polymer?

The polysaccharide of glucose called cellulose, a polymer with strong intermolecular hydrogen bonds that give these materials such excellent physical properties.The polysaccharide of glucose called starch; it's also found in legumes and potatoes.Proteins such as collagen that are strong and have extensive intermolecular hydrogen bonding holding them together.The polysaccharide with sucrose repeat units, which is why sucrose is so cheap and readily available.

14. Substituents on aromatic molecules can have long-range effects: explain why.

Sigma bonds transmit electronic effects by electronic polarization effects.Resonance causes spreading of the electronic effects of various substituents throughout the ring through sigma bonds.Resonance of the electron donating or withdrawing affects of a substituent can stabilize or destabilize charge at ortho and para positions.Through space interactions of a substituent with sigma bonds in the ring affect individual carbon electron densities.

15. Naphthalene (10 carbons with two fused benzene rings) is aromatic according to Huckel because:

there is a continuous array of p-orbitals from pi-bonds around the outside of the fused rings AND there are 4n + 2 electrons in them (10).fused benzene rings are always aromatic.None of these.10 carbons are an even number and there are 5 double bonds with 8 pairs of electrons in them.

16. Carboxylic acids form salts with amines that can be useful how?

You can extract impurities away using water plus an organic solvent.You can heat the salt up under vacuum and form an amide (usually).All of these, in a practical sense.They're more water soluble as the salt, and if one is a medication, this can help in delivery.

17. Almost all EAS reactions require a catalyst because (pick the best answer below):

The catalyst brings the aromatic ring and the electrophile together so that they can react.Actually, a catalyst is rarely used and this is a false statement.The catalyst complexes with the aromatic ring to activate it for attack.EAS is a difficult reaction since your going uphill energetically from an aromatic molecule, and the catalyst helps do this by forming a more reactive electrophile.

18. Carboxylic acids can react by:

conversion to acid chlorides with thionyl chloride, a high-energy and very reactive inorganic acid chloride.rehybridization of the central sp2 carbon to an sp3 one.electrophilic attack of an amine on the central carbon of the acid group.nucleophilic attack of the polarized central carbon of the acid group on alcohols and amines.

19. There are many ways to make an ether including:

reaction of an alkoxide and an alkyl bromide.reaction of two alcohols with base and heat catalysis.reaction of an epoxide with an alkene using acid catalysis.addition of water to an epoxide with base catalysis.

20. Synthesis of a carboxylic acid can occur by:

conversion of the alcohol OH to an alkyl halide with thionyl chloride.reaction with oxygen in the air catalyzed by heat.reaction of an alkene with a peracid or peroxide plus acid catalyst.reaction of an alcohol with a strong oxidizing agent like KMnO4.

21. If you wanted to make your own soap, how would you do it?

Take cotton fibers and mix with a strong base such as lye, add water, boil till the fibers dissolve, filter and evaporate the water.Add fur or wool to water containing strong acid, boil till everything dissolves, filter and evaporate the water to give the slippery crude soap.Start with animal fat or a plant oil, mix with lye (strong inorganic base) and water, heat till all the fat or oil dissolves, filter and evaporate the water to give the fatty acid salt (soap).Clot cream with acetic acid, mix the curds you get with yeast and let ferment until the bubbling stops; evaporate the water to get soap.

22. Substituents on aromatic ring can affect each other: Pick the answer that best illustrates this.

3, 4-Dinitrobenzoic acid is readily made by nitration of benzoic acid with excess fuming nitric acid.The order of acidity of substituted benzoic acid increases for para-substituents nitro, chloro, hydroxy.The more electron withdrawing groups on the ring, the more acidic is benzoic acid; i.e., trichloro more than dichloro more than monochlorobenzoic acid.Meta-nitrobenzoic acid is more acidic than the para-nitro isomer because the nitro is closer to the acid group.

23. Amides are derivatives of carboxylic acids that:

first reacting the acid with sodium hydroxide and then adding the amine.can be formed by simple mixing of an amine with an acid.first reacting the amine with thionyl chloride and then adding the acid.first reacting the acid with thionyl chloride and then adding the amine.

24. There are two components to a nucleophilic aromatic substitution reaction with the order of reactivity of:

other activating groups that are NOT displaced but stay on the ring such as ester, nitro, sulfone and carbonyl.the nature of the attacking nucleophile being unimportant.halide leaving groups on the aromatic ring being F>Cl>Br, I not reactive.All of these.

25. Do eletrophilic compounds always react at the sulfur, no matter what?

Yes, except when oxygens are attached to the sulfur, then the oxygens react first.Yes, except when carbons are attached to the sulfur, then substitution occurs at the carbon.Pretty much, yes, even when oxygens are attached to the sulfur.Yes, except when bromine is involved.

25 Questions

❤ If you liked Fatskills, consider supporting us by checking out The Life Manuals You Never Got.

About | Explore | User Guide | Topics | Subjects | Doubt Solver | Career Aptitude Test | Answers | Free Tools | What Should We Know?
Privacy | Terms |

Without work one finishes nothing. - Ralph Waldo Emerson
© 2026 Fatskills.com

All trademarks, logos and brand names are the property of their respective owners. All company, product and service names used in this website are for identification purposes only. Use of these names, trademarks and brands does not imply endorsement.

25 Questions

❤ If you liked Fatskills, consider supporting us by checking out The Life Manuals You Never Got.

About | Explore | User Guide | Topics | Subjects | Doubt Solver | Career Aptitude Test | Answers | Free Tools | What Should We Know? Privacy | Terms |

Without work one finishes nothing. - Ralph Waldo Emerson© 2026 Fatskills.com

All trademarks, logos and brand names are the property of their respective owners. All company, product and service names used in this website are for identification purposes only. Use of these names, trademarks and brands does not imply endorsement.

About | Explore | User Guide | Topics | Subjects | Doubt Solver | Career Aptitude Test | Answers | Free Tools | What Should We Know?
Privacy | Terms |

Without work one finishes nothing. - Ralph Waldo Emerson
© 2026 Fatskills.com