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

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

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

2. Friedel-Crafts acylation of ortho-nitrotoluene with acetyl chloride and aluminum trichloride gives:

no reaction since the nitro group is so deactivating.2-methyl-acetophenone by nitro group displacement.almost exclusively a single product, 3-nitro-4-methyl-acetophenone.a mixture of acetophenones with the nitro group always ortho or para to the carbonyl.

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

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

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

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

5. The Kolbe and Riemer-Tieman reactions are special types of EAS reaction in which:

phenol dissolved in ethanol with iron chloride reacts rapidly with carbonic acid to form the ortho- and para-hydroxybenzoic acids.chloroform is the electrophile and it reacts with the sodium salt of phenol (sodium phenolate).bubbling carbon dioxide through a solution of phenol in water generates the para-hydroxybenzoic acid.sodium phenolate (sodium salt of phenol) reacts directly with carbon dioxide (high temperature and pressure) to give ortho- and para-hydroxybenzoic acids as their sodium salts.

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

7. The reactivities of substituents on aromatic rings are affected by the aromatic ring as illustrated by which of the following answers?

Benzoic acid is more acidic than acetic acid.All of these.Styrene or vinylbenzene is a better free radical monomer then propene.The methyl group of toluene readily undergoes free radical reaction and oxidation.

9. You can make butene alcohol by:

reacting with hydrogen peroxide and acetic acid.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.

10. Reaction of isopropyl bromide (2-bromopropane) with amines varies how with amine structure?

Only primary and secondary amines react due to steric inhibition with tertiary amines.It doesn't vary at all since all amines and ammonia have the same basic reactivity.In a non-regular manner, with secondary amines often being more reactive than either primary or tertiary amines.Because of steric inhibition caused by the huge isopropyl group, there is no reaction with any amines.

11. The two types of aromatic substitution reactions (electrophilic and nucleophilic) are complementary in that (pick the best answer):

The same types of substituents on the aromatic ring are activators in both cases.Both use Lewis acid catalysts like iron chloride or aluminum chloride.EAS is enhanced by electron donating groups on the ring while NAS is enhanced by electron withdrawing groups.The arrow showing electron motion in both cases always starts at one of the pi bonds on the ring.

12. Sucrose is an excellent example of what kind of natural material?

Oligomers and polymers of glucose, the most common of the sugars, with sucrose composed of two glucose monosaccharides.An artificial sweetener made of glucose and fructose units with non-natural stereochemistry at the anomeric carbons.The monosaccharide that forms part of the polymer chain in RNA and DNA.Natural monosaccharides such as hexoses and pentoses, although sucrose is a dimer sugar with two different monosaccharides.

13. Butyl amine and acetic acid will react:

with an butyl bromide to form dibutyl amine.in ethanol to form an ester and amine salt.with heat to drive off water and make N-butyl acetamide.hydrochloric acid to form an amide.

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

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.The cyclohexanone dimerizes and then formaldehyde donates a hydride to reduce the remaining ketone to give the diol.

15. Ethers can react with which of the following?

With acid and another alcohol to give transetherification- another ether and a different alcohol from the starting one.With a carboxylic acid and heat to give an ester and an alcohol.With ethyl bromide to give an ethyl ether and a new alkyl bromide.With base and water to give two alcohols.

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

Nature uses acid chlorides (acyl halides) in the body to make natural amides such as peptides.Nitriles have a carbon-nitrogen 'double bond' and are also called Shiff bases.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).

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

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.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.

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

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 mix NaSH with ethanol and then add the aromatic molecule to make the aryl sulfide.You decide on sodium methoxide dissolved in water to makethe para-nitrophenyl methyl ether.

19. What is the difference between a thiol and a mercaptan?

A mercaptan is like an alcohol (SH bond) while a thiol is like an ether.There is none; they're the same and they both have SH bonds.A thiol is the sulfur analog of an ether; a mercaptan is like an alcohol (SH bond).There is none; they're both ether analogs (C-S-C bonds).

20. Pick the synthetic conditions that will make an ether.

the conditions for a Williamson synthesis (alkoxide plus halide).Reaction of an epoxide with a carboxylic acid.Conversion of an alcohol with base catalysis and heat, distilling off the ether as it forms.Reaction of an alkyl halide with NaOH in water.

21. The genetic code of all plants and animals is composed of what polymer?

Natural polyamides making up collegen, proteins and peptides.Polymers of nucleic acid bases with phophoric acid to give complex polyesters abbreviated RNA and DNA.Natural (what else?) polyamides called DNA and RNA which contain nucleic acid bases in the repeat units.Lipid polymers that contain nucleic acid bases organized in three-unit sequences.

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

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

23. 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.

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

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

25. 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 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.The OH oxygen reacts twice to give the bisester derivative.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.Ring acylation occurs twice in the ortho-ortho' and ortho-para positions.

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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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