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

1. Aniline is an aromatic amine that can be made how?

By treating benzene with nitric acid in sulfuric acid, isolating the nitrobenzene and reducing with hydrogen and a palladium catalyst.Heating benzene with ammonia under high heat and pressure; once the first amine adds, further reaction stops because the amine is such a strong electron donator.Reacting phenol with thionyl chloride to form chlorobenzene, then heating with ammonia under high temperature and pressure.Reacting benzene with chlorine gas and iron chloride catalyst, then nitrating with nitric acid in sulfuric acid, isolating the product and reducing with hydrogen using a palladium catalyst.

2. There are three types of amines that include:

alkyl, aryl (aromatic), and ammonium salts.primary, secondary, and tertiary, referring to the type of carbon directly attached to the nitrogen.primary, secondary, and tertiary, referring to how many alkyl carbons are directly attached to the nitrogen.substituted amines, unsubstituted amines, and amides.

3. Pyridine is an aromatic amine: what is its structure and is it basic?

It is a seven-membered ring with the six sp2 hybridized carbons accounting for the aromaticity and the nitrogen in the ring providing basicity.It is like benzene with one carbon replaced with nitrogen that also has a lone pair of electrons (basic) in an sp2 orbital within the plane of the ring.Pyridine is one of the nucleic acid bases possessing two nitrogens in the aromatic (benzene-like) ring and one nitrogen NH2 attached.Pyridine is a benzene ring with an NH2 group attached that is basic like any amine.

4. Ketones and aldehydes react with HCN to give what?

The dicyano compound with both CN's attached to the carbonyl carbon and one equivalent of water released.Poisonous materials that are extremely dangerous due to reversible release of the HCN.A member of the family of adducts called cyanohydrins, which can be hydrolyzed to the alpha-hydroxy acid.Reaction at the alpha-position of the enol form of the carbonyl to give a beta-cyano ketone or aldehyde.

5. Why is a hydrogen attached to the carbon next to a carbonyl so reactive?

The carbonyl polarization pushes electrons onto the alpha-carbon and hydrogen through sigma bonds.Enol-keto tautomers equilibrate and the hydrogen isnIn the anionic intermediate formed, delocalization of charge onto the more electronegative oxygen occurs through pi-bonds.The double bond to oxygen from the alpha carbon is conjugated to the intermediate carbanion through a double bond to that carbon as well.

6. 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 NaH reduces both carbonyls to alcohols.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 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.The first step gives 2-chloro-1, 5-cyclooctadione but the second NaH reduces off the chlorine to give back the starting material.

7. Carboxylic acids have a unique combination of:

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

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

A complex carbohydrate containing both saccharides and amino acids in the polymer repeat units.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 mixture of inorganic phosphate and cellulose that has extremely strong intermolecular forces holding the chains together.

9. EAS with chlorine gas bubbled into chlorobenzene containing aluminum trichloride would:

gives mostly meta-dichlorobenzene with mild heating.not happen because chlorine is deactivating.generates HCl and mostly para-dichlorobenzene.gives mostly ortho-dichlorobenzene with mild heating.

10. The aldol reaction of acetaldehyde (2 carbons) with sodium ethoxide catalyst gives what?

A dimer of the aldehyde (kind of) that could be named 3-hydroxy-1-butanal.A dimer joined at what were the carbonyl carbons, the product named as 2, 3-butandiol.No reaction- ethoxide is not a strong enough base to actually catalyze any reaction of acetaldehyde.Addition of two equivalents of the ethoxide to the carbonyl carbon to form the acetal.

11. The Claissen-Schmidt reaction is a simple reaction (cyclohexanone plus 1 equivalent formaldehyde and sodium ethoxide catalyst) that forms what product?

The cyclohexanone dimerizes and then formaldehyde donates a hydride to reduce the remaining ketone to give the diol.Abstraction of proton alpha to the ketone followed by attack at the formaldehyde carbonyl followed by a two-step proton exchange and water loss to form the alpha methylene ofcyclohexanone.The ethoxide attacks the formaldehyde first (more reactive carbonyl) and the adduct attacks the ketone to form the acetal.Since the formaldehyde is more reactive, it adds the ethoxide and the resulting carbanion adds to the ketone carbonyl followed by loss of water to give cyclohexenylmethanal.

12. 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.Reaction of an acid chloride with a reasonably activated aromatic using a strong Lewis acid catalyst.Slowly adding a carboxylic acid to a mixture of concentrated nitric acid and the aromatic compound.

13. Of the 20 natural amino acids listed in the reading, 10 are called 'essential', meaning what?

Your body doesn't really need or use the non-essential ones, while the essential ones make up all the proteins your body needs.While your body can 'manufacture' the non-essential ones from what you eat, it can't make the essential ones so you have to make sure you eat the right balance of foods to get them in your diet.You must take vitamins to make sure you get enough of these essential amino acids to survive.That without them, you would die a slow, painful death.

14. Amines are 'basic' in a Bronstead scheme because of what?

That's just the way they roll.A proton can bind to one of the attached atoms through the excess electron density in the bonding orbital.They have a lone pair of electrons in an sp3 orbital just sitting there waiting for something to happen, like protonation.They have a conjugated set of orbitals capable of forming dative bonds.

15. All EAS reactions involve a 'tetrahedral' or Td intermediate. Which of the following is true of this statement?

No, the leaving group leaves at the same time the attacking group forms a bond.Can't happen with an aromatic ring carbon which by definition is sp2 or trigonal planar.There is no intermediate in EAS which simple involves attack at electrons.Almost all do: an sp2 carbon becomes sp3 in the intermediate.

16. The acidity of a proton (hydrogen) alpha to most carbonyl compounds is around pKa = 25, but drops to what with two carbonyls attached to the same sp3 carbon with a hydrogen?

Less than 6 which makes them about as acidic as carboxylic acids.Less than 20 but just barely.Less than 10 which makes them weak acids.Less than 14 or so which means that aqueous base can deprotonate such compounds.

17. How would you best make a conjugated diene?

React a four carbon (at least) linear alkane with two equivalents of chlorine under UV light, then dehydrohalogenate twice with KOH in alcohol.Take any 4-carbon alkene, add bromine across the double bond and dehydrohalogenate twice with KOH in alcohol.First chlorinate and dehydrochlorinate butane, then deprotonate with butyl lithium or concentrated KOH in alcohol, and pour the mixture into dilute acid to neutralize the base.Starting with a linear alkane with at least four carbons, first halogenate once and dehydrohalogenate to an alkene; do radical allylic halogenation to give an allyl halide; then dehydrohalogenate again with KOH in alcohol to the diene.

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

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

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

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

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

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

21. A neat way to make a symmetrical dialdehyde from cyclohexene is done how?

Reacting the alkene with ozone (O3) in chloroform (CHCl3) followed by treatment with peroxide.Treating first with osmium tetroxide in pyridine, then adding hydrogen sulfide and extracting the product.Reacting the alkene with hydrogen peroxide in acetic acid followed by adding water plus heat to give a glycol that is then cleaved with more peroxide and heat.All of these, I hope.

22. An alkyl carboxylic acid can be made by:

oxidation of a primary alcohol with hot permanganate or chromate.reacting an alcohol with ozone.heating a methyl ketone with acid and iodine.treating an alkyl halide with hydrogen gas and platinum.

23. The basic order of stability of carboxylic acids is (pick one).

acids > acyl halides > esters > anhydrides > amidesamides >> acids > esters > acyl halides > anhydridesesters > amides > acids >> anhydrides > acyl halidesamides >> acids ~ esters > anhydrides > acyl halides

24. Reaction of 1, 3-butadiene with maleic anhydride gives a single product that is:

a 1:1 copolymer of the two reactants.3-(3-butenyl)succinic anhydride.4-cyclohexene-cis-dicarboxylic acid anhydride.3-vinylcyclobutane-1, 2-dicarboxylic acid anhydride.

25. The Williamson ether synthesis involves which of the following?

The two Williamson reagents normally used in combination with heat and light.An alkyl alcohol heated up with acid to distill off water.An alkoxide salt of an alcohol reacted with a primary or secondary halide.An alkoxide salt of an alcohol reacted with the alcohol it was made from.

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