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

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

All of these, I hope.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.Treating first with osmium tetroxide in pyridine, then adding hydrogen sulfide and extracting the product.Reacting the alkene with ozone (O3) in chloroform (CHCl3) followed by treatment with peroxide.

2. You decide to make meta-nitrophenol by doing which of the following steps?

Reacting benzene with chlorine/iron, then reacting the product with nitric acid followed by NaOH in water.Reacting phenol with fuming nitric acid in an ice bath.Reacting benzene with fuming nitric acid to make trinitrobenzene and then with NaOH in water.Reacting benzene with fuming nitric acid, then reacting the product with chlorine/iron, and last heating with NaOH in water.

3. The NAS mechanism is special in what regard?

The aromatic nucleus being attacked must have electron donating groups attached.It involves nucleophilic attack at an sp2 carbon which only occurs with strong electron withdrawing groups attached at or in resonance with the substituted carbon.It requires a much more nucleophilic attacking species than in alkyl substitution reactions.A 3-center Intermediate exists involving the catalyst, nucleophile and aromatic ring.

4. Fuming nitric acid converts phenol into:

2, 4-dinitrophenol because of deactivation with each nitro group added.pure trinitrophenol (also called 'picric acid' which has a really low pKa for a phenolic compound).a complex mixture of ortho- and para-substituted phenols with di- and trinitro derivatives predominating.para-nitrophenol since the OH group on an aromatic ring is activating and ortho-para directing.

5. Epoxides are a special kind of ether that:

are reactive because of ring string (3 membered ring).can react with amines, alcohols and acids.All of these.react faster with acid or base catalysis.

6. Which of the following statements is true about a carboxylic derivative or reaction?

Nitriles have a carbon-nitrogen 'double bond' and are also called Shiff bases.Nature uses acid chlorides (acyl halides) in the body to make natural amides such as peptides.An imide is a carbonyl with two nitrogens attached (like ureas).The key atoms of an amide bond (carbon and oxygen of the carbonyl plus the amide of the nitrogen and its hydrogen) all lie in the same plane making for a rigid, conformationally restrained segment (like in an enzyme).

7. An epoxide reacts with an alkoxide to give an ether plus something else:

and the something else is another epoxide.and the something else is another alkoxide.and there is nothing else formed.and the something else is NaOH.

8. You find to your surprise that the reaction of phenol with acetic anhydride and aluminum trichloride gives a mixture of two disubstituted products. Pick the best reason for why.

The OH oxygen reacts twice to give the bisester derivative.The first acylation product is in the ortho and para positions which deactivates the ring and causes meta-substitution with the second acetyl group to give ortho-meta and meta-para diacetylphenols.Ring acylation occurs twice in the ortho-ortho' and ortho-para positions.The first reaction is at the oxygen to give phenyl acetate followed by acetylation in the ortho and para positions to give a mixture of products.

9. The Swern oxidation involves using DMSO (remember this great solvent?) to do what?

React with oxygen to form dimethylsulfone, the di-oxygen derivative of sulfur.Convert a primary alcohol to a carboxylic acid using oxygen as the co-reactant.React with primary or secondary alcohols to give aldehydes or ketones.Convert amines to oxides such as nitric oxide using peroxide as co-reactant.

10. What is the key intermediate(s) of the reactions of many acid derivatives?

That would have to be the Td or tetrahedral intermediate involved in the most common type, the addition-elimination mechanism.Trick question: there is only a transition state in most acid reactions.Acid reaction mechanisms are very much like an Sn1 mechanism with the loss of the leaving group occurring first to give an acylonium ion.Acid reaction mechanisms are very much like an Sn2 reaction with simultaneous bond-formation and bond-breaking.

11. There are three types of amines that include:

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

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

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.carefully adding excess chlorine followed by excess KOH in alcohol.heating it in the presence of a hydrogen and a catalyst such as palladium.

13. You acquire a mixture of meta- and para-fluoronitrobenzene and want to react it with a nucleophile. What should you do first?

You mix NaSH with ethanol and then add the aromatic molecule to make the aryl sulfide.You choose NaCl in ethanol since that's a pretty good nucleophile system.You pick sodium methoxide because it's more reactive than a sulfur anion, sodium hydrosulfide (NaSH).You decide on sodium methoxide dissolved in water to makethe para-nitrophenyl methyl ether.

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

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.Rapid resonance of pi electrons spreads the electron density over more atoms.A more even distribution of pi electrons occurs in aromatic molecules.There is no good explanation that we know of, it's just a fact of nature.

15. 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 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 NaH reduces both carbonyls to alcohols.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.

16. You can make butene alcohol by:

carefully adding one equivalent of HCl followed by NaOH in water.simply heating 1, 3-butadiene with NaOH in water.carefully adding one equivalent of bromine followed by NaOH in water.reacting with hydrogen peroxide and acetic acid.

17. Carboxylic acids can react by:

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

18. Amides are derivatives of carboxylic acids that:

first reacting the acid with sodium hydroxide and then adding the amine.first reacting the acid with thionyl chloride 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.

19. Alcohols are unique in forming ethers because:

they have higher boiling points than hydrocarbons or ethers with the same number of carbon atoms.they are All of these.they can react with themselves in the presence of heat and acid to give ethers.they have an exchangeable hydrogen (the OH one).

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

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

21. 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.

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

23. Alcohols react using both acid and base catalysis: please elaborate.

Acids and bases will react in alcohols to form salts that are useful for ether synthesis.Acids catalyze alcohol dimerization to ethers while bases hydrolyse them.Acids are used as catalysts in the Williamson ether synthesis and for hydrolysis of ethers.Bases dissolve in ethers for use in other reactions.Acids catalyze hydrolysis and ether formation from alcohols.Bases polarize the OH bond, even to the point of forming an alkoxide salt.

24. 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.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.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.

25. Which is the best way to make an amide from a carboxylic acid derivative?

Use the classic Shotten-Baumen conditions of one equivalent of acid chloride in an organic solvent and one equivalent of amine plus one equivalent of dilute inorganic base in water, stir rapidly, chill as needed.Use an anhydride with two equivalents of amine, one for each of the acid equivalents (oh, and add heat).Use two equivalents of amine with one equipment of acid chloride.React an ester with an amine through heat-induced transamidation.

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25 Questions

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

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