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

1. 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.An imide is a carbonyl with two nitrogens attached (like ureas).Nitriles have a carbon-nitrogen 'double bond' and are also called Shiff bases.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).

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

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.Add fur or wool to water containing strong acid, boil till everything dissolves, filter and evaporate the water to give the slippery crude soap.Take cotton fibers and mix with a strong base such as lye, add water, boil till the fibers dissolve, filter and evaporate the water.

3. EAS reactions involve attack by something seeking:

a one-step reaction involving loss of leaving group at the same time the attacking group makes a new bond.electrons, and those are almost always relatively 'available' ones in pi-orbitals.a nucleus to bond to, making the reaction also a 'nucleophilic' attack.all of the below.

4. In terms of basicity, what is the order for alkyl amines?

Ammonia > primary amine > secondary > tertiary due to electron withdrawing ability of any heteroatom.Tertiary amine > secondary > primary > ammonia due to electron donating ability of alkyl substituents.It will depend on whether we're talking about Lewis or Bronstead acid-base chemistry.Secondary > tertiary > primary > ammonia due to steric effects for the tertiary putting it 'out of order.'

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

6. Fuming nitric acid converts phenol into:

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

7. Ethers can react with which of the following?

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

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

Acids catalyze hydrolysis and ether formation from alcohols.Bases polarize the OH bond, even to the point of forming an alkoxide salt.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.

9. In a different problem (somewhere here) you oxidized an alcohol to an aldehyde or ketone; now you want the alcohol back so you:

Add concentrated NaOH in water and heat to drive off the water, then extract with methylene chloride to obtain the alcohol.Dissolve the ketone or aldehyde in ethanol (maybe with a little water and NaOH added) and then slowly adding sodium borohydride followed by neutralization and extraction.Add to the carbonyl compound in ethanol concentrated sulfuric acid containing sodium borohydride, then neutralizing and extracting with ether.Treat with hot potassium permanganate (KMnO4) in aqueous acid, then neutralize and extract.

10. The amide groups of peptides, proteins and enzymes have what unique property?

Because of the sp2 hybridization of the carbonyl and attached nitrogen, the amide group is 'flat' and capable of strong hydrogen bonding with other amide groups.The free rotation around the carbonyl bond to the nitrogen allows these amino acid polymers to flex and bend as needed in the body.The nitrogen group is basic and can form ammonium salts with carboxylic acids of other amino acids.Like ketones, they can tautomerize to switch the hydrogen on nitrogen over onto the carbonyl oxygen, leading to enhanced hydrogen bonding.

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

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.Trick question: there is only a transition state in most acid reactions.That would have to be the Td or tetrahedral intermediate involved in the most common type, the addition-elimination mechanism.

12. 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 complex mixture of inorganic phosphate and cellulose that has extremely strong intermolecular forces holding the chains together.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.

13. Under what conditions can hydrolysis of a carboxylic ester or amide lead back to the acid?

Treating with NaH and ethanol.Boiling with alcohol and acid catalyst.Boiling with water and base catalyst.Simply mixing with water and stirring at room temperature.

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

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

15. What is the best way to draw (describe) the sodium salt of 2, 4-pentadione (two acetyls on the same methylene)?

Since only one of the oxygens can undergo enol-keto tautomerism, the sodium cation should be on one oxygen.Since both oxygens can equilibrate with the carbanion, why not put the sodium cation between them in a chelate?Since only one hydrogen on the carbon is lost to form this, the sodium cation should be on the alpha carbon.Since the carbonyl oxygen lone pairs repel each other, one carbonyl will be twisted out of plane with the other, and will have the sodium attached.

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

They have a conjugated set of orbitals capable of forming dative bonds.They have a lone pair of electrons in an sp3 orbital just sitting there waiting for something to happen, like protonation.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.

17. 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.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.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.

18. 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.Pyridine is a benzene ring with an NH2 group attached that is basic like any amine.Pyridine is one of the nucleic acid bases possessing two nitrogens in the aromatic (benzene-like) ring and one nitrogen NH2 attached.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.

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

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

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

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

21. Acid chlorides are highly reactive derivatives of carboxylic acids that can:

be made from alkyl alcohols by reaction with thionyl chloride.react with amines and alcohols to give amides and esters.react with themselves to form ketones.be reduced to ketones with hydrogen and a platinum catalyst.

22. Carboxylic acids can react to:

form alcohols by oxidation with peracids.form alkyl bromides by reaction with PBr3.form amides by reaction with amines, heat and water removal by distillation.form an ester by reaction with an ether.

23. 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.

24. 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.

25. The relative energies used in various kinds of spectroscopic methods vary how?

It's not really the energy used, since this can vary independently of frequency or wavelength.You can't really compare the energies since each type of spectroscopy uses a unique mixture of frequencies.From low energy ultraviolet rays to infrared and then to microwaves used in NMR analysis and finally high energy electrons in mass spectrometry.From high frequency radio waves to lower frequency electrons for NMR to infrared to UV to mass spectrometry.

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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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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?
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Without work one finishes nothing. - Ralph Waldo Emerson
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