Pharmaceutical Chemistry
Pre-Test Questions
Course Introduction
Pharmaceutical Chemistry explores the design, synthesis, analysis, and development of bioactive compounds with therapeutic potential. The course covers the principles of medicinal chemistry, including drug discovery, structure-activity relationships (SAR), mechanisms of drug action, and the pharmacokinetics and pharmacodynamics of pharmaceutical agents. Students will learn about various classes of drugs, their chemical properties, modes of action, metabolism, and the processes involved in bringing a drug from laboratory research to clinical use, as well as the regulatory aspects and quality control in the pharmaceutical industry.
Recommended Textbook
Organic Chemistry 8th Edition by Paula Yurkanis Bruice
Available Study Resources on Quizplus
28 Chapters
3204 Verified Questions
3204 Flashcards
Source URL: https://quizplus.com/study-set/3708
Page 2
Chapter 1: Remembering General Chemistry: Electronic
Structure and Bonding
Available Study Resources on Quizplus for this Chatper
90 Verified Questions
90 Flashcards
Source URL: https://quizplus.com/quiz/73830
Sample Questions
Q1) The N-H bond in the ammonium ion,NH<sub>4</sub><sup>+</sup>,is formed by the overlap of what two orbitals?
A)sp<sup>3</sup>-sp<sup>3</sup>
B)sp<sup>3</sup>-sp<sup>2</sup>
C)sp<sup>2</sup>-sp<sup>2</sup>
D)sp<sup>2</sup>-s
E)sp<sup>3</sup>-s
Answer: E
Q2) Give the formal charge on nitrogen in NH<sub>4</sub>.
A)-2
B)-1
C)0
D)+1
E)+2
Answer: D
Q3) Covalent bonds may be polar or nonpolar.What property of the atoms forming a given bond determines this?
Answer: electronegativity
Q4) Draw the Lewis structure for CH<sub>3</sub>N<sub>2</sub><sup>+</sup>.
Answer: 11ea8a1c_2c63_6437_b657_ad9742f6e368_TB1831_00
To view all questions and flashcards with answers, click on the resource link above. Page 3
Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
Available Study Resources on Quizplus for this Chatper
43 Verified Questions
43 Flashcards
Source URL: https://quizplus.com/quiz/73831
Sample Questions
Q1) When a small amount of hexanoic acid [CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub>H,pKa~4.8],is added to a separatory funnel which contains the organic solvent diethyl ether and water with a pH of 2.0,it is found mainly in the ________ phase as ________. A)ether; CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub><sup>-</sup> B)water; CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub><sup>-</sup> C)ether; CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub>H D)water; CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub>H E)none of the above
Answer: C
Q2) At what pH will 25% of a compound with a pKa of 5.3 be in its basic form?
Answer: 4.8
Q3) The pKa of CH<sub>3</sub>COOH is 4.8 and the pKa of HCOOH is 3.8.Given this information,one knows that A)CH<sub>3</sub>COOH completely ionizes in water. B)HCOOH is a weaker acid than CH<sub>3</sub>COOH. C)HCOO<sup>-</sup> is a weaker base than CH<sub>3</sub>COO<sup>-.</sup> D)CH<sub>3</sub>COOH reacts with HO<sup>-</sup> while HCOOH does not.
E)HCOOH reacts with HO<sup>-</sup> while CH<sub>3</sub>COOH does not.
Answer: C
To view all questions and flashcards with answers, click on the resource link above. Page 4
Chapter 3: An Introduction to Organic Compounds:
Nomenclature, physical Properties, and Structure
Available Study Resources on Quizplus for this Chatper
136 Verified Questions
136 Flashcards
Source URL: https://quizplus.com/quiz/73832
Sample Questions
Q1) Draw the most stable conformer of cis-1-ethyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7f_030c_b657_0556aed4dd3f_TB1831_00
Q2) Draw the most stable conformation of trans-1-isopropyl-2-methylcyclohexane.
Answer: 11ea8a1c_2c7e_8dda_b657_e1b785ae35ad_TB1831_00 or enantiomer
Q3) Use a sawhorse structure to depict the eclipsed conformer of ethane.
Answer: 11ea8a1c_2c7c_b90d_b657_5367c2365501_TB1831_00
Q4) Which of the following compounds does not have the molecular formula C<sub>6</sub>H<sub>14</sub>O?
A)1-hexanol
B)2-hexanol
C)3-methyl-2-pentanol
D)3-methyl-3-pentanol
E)cyclohexanol
Answer: E
Q5) Which compound is more soluble in water? Briefly explain your choice. CH<sub>3</sub>OCH<sub>3</sub> or CH<sub>3</sub>CH<sub>2</sub>OH
Answer: CH<sub>3</sub>CH<sub>2</sub>OH is more soluble in water since it can donate a hydrogen bond to water and accept a hydrogen bond from water.CH<sub>3</sub>OCH<sub>3</sub> can only accept a hydrogen bond from water; it has no hydrogen which can hydrogen bond to water.
To view all questions and flashcards with answers, click on the resource link above. Page 5
Chapter 4: Isomers: the Arrangement of Atoms in Space
Available Study Resources on Quizplus for this Chatper
125 Verified Questions
125 Flashcards
Source URL: https://quizplus.com/quiz/73833
Sample Questions
Q1) Provide a perspective drawing of each diastereomer of (2R,3S)-1,2,3-trichloropentane.
Q2) Which of the following is not true of enantiomers?
A)They have the same melting point.
B)They have the same boiling point.
C)They have the same chemical reactivity with non-chiral reagents.
D)They have the same density.
E)They have the same specific rotation.
Q3) Can one predict whether a compound with a single asymmetric center is dextro- or levorotatory based on the R/S assignment at this asymmetric center? Explain briefly.
Q4) Which of the following statements correctly pertains to a pair of enantiomers?
A)They rotate the plane of polarized light by exactly the same amount and in opposite directions.
B)They rotate the plane of polarized light by differing amounts and in opposite directions.
C)They rotate the plane of polarized light by differing amounts and in the same direction.
D)They have different melting points.
E)They have the same melting point,but they have different boiling points.
To view all questions and flashcards with answers, click on the resource link above. Page 6
Chapter 5: Alkenes: Structure,nomenclature,and an
Introduction to Reactivity - Thermodynamics and Kinetics
Available Study Resources on Quizplus for this Chatper
84 Verified Questions
84 Flashcards
Source URL: https://quizplus.com/quiz/73834
Sample Questions
Q1) The Arrhenius equation models how the rate constant k
A)increases as both E<sub>a</sub> and T increase.
B)increases most when E<sub>a</sub> increases and T decreases.
C)increases most when E<sub>a</sub> decreases and T increases.
D)increases as both E<sub>a</sub> and T decrease.
E)increases as reactant concentrations increase.
Q2) Give the possibilities in structure for a compound with a formula of C<sub>6</sub>H<sub>10</sub>.
A)no rings,no double bonds,no triple bonds
B)one double bond,or one ring
C)two rings,two double bonds,one double bond + one ring,or one triple bond
D)three rings,three double bonds,two double bonds + one ring,one ring + two double bonds,one triple bond + one ring,or one double bond + one ring
E)benzene
Q3) The G° for the conversion of "axial" isopropylcyclohexane to "equatorial" isopropylcyclohexane at 298K is -2.1 kcal/mol.Calculate the percentage of isopropylcyclohexane molecules that have the isopropyl substituent in the axial position at this temperature.
[R = 1.987 × 10<sup>-3</sup> kcal mol<sup>-1</sup>K<sup>-1</sup>]
Page 7
To view all questions and flashcards with answers, click on the resource link above.
Chapter 6: The Reactions of Alkenes - the Stereochemistry
of Addition Reactions
Available Study Resources on Quizplus for this Chatper
89 Verified Questions
89 Flashcards
Source URL: https://quizplus.com/quiz/73835
Sample Questions
Q1) Identify the true statements in the mechanism in the addition of water to an alkene.
A)The addition of the electrophile is a slow step.
B)The addition of the nucleophile is a fast step.
C)A carbocation is formed as an intermediate.
D)Water abstracts the extra proton from the protonated alcohol.
E)all of the above
Q2) What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?
A)2-methylpentane
B)2-methyl-1-pentanol
C)2-methyl-2-pentanol
D)2-methyl-3-pentanol
E)1-methoxypentane
Q3) Which statement is true in the hydroboration-oxidation of an alkene?
A)Markovnikov orientation and syn addition occur.
B)Markovnikov orientation and anti addition occur.
C)Anti-Markovnikov orientation and syn addition occur.
D)Anti-Markovnikov orientation and anti addition occur.
E)Markovnikov orientation and both syn and anti addition occur.
Page 8
To view all questions and flashcards with answers, click on the resource link above.
Chapter 7: The Reactions of Alkynes - Introduction to Multistep Synthesis
Available Study Resources on Quizplus for this Chatper
124 Verified Questions
124 Flashcards
Source URL: https://quizplus.com/quiz/73836
Sample Questions
Q1) Draw an acceptable structure for 2-hexyne.
Q2) Give the IUPAC name for (CH<sub>3</sub>)<sub>2</sub>C(CH<sub>2</sub>CH<sub>3</sub>)CCCH(CH<sub>3</ sub>)<sub>2</sub>.
Q3) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
Q4) In the reduction of alkynes using sodium in liquid ammonia,which of the species below is not an intermediate in the commonly accepted mechanism?
A)vinyl anion
B)vinyl radical
C)radical anion
D)vinyl cation
Q5) In the hydroboration-oxidation reaction of a terminal alkyne,the product is a(n)
A)alkyne
B)aldehyde
C)ketone
D)enol
E)alcohol
Page 9
Q6) Provide the structure of the major organic product that results when 2-butyne is treated with 2 equivalents of HCl.
To view all questions and flashcards with answers, click on the resource link above.
Page 10
Electronic Effects: an Introduction to the Reactions of
Benzene
Available Study Resources on Quizplus for this Chatper
185 Verified Questions
185 Flashcards
Source URL: https://quizplus.com/quiz/73837
Sample Questions
Q1) Show how the p orbitals overlap to form the nonbonding molecular orbital of the allyl system.
Q2) Rank the following dienes in order of increasing stability: trans-1,3-pentadiene,cis-1,3-pentadiene,1,4-pentadiene,and 1,2-pentadiene.
Q3) Why does the (E,E)-isomer of 2,4-hexadiene react much more rapidly with dienophiles than does the (Z,Z)-isomer?
Q4) What is the major product obtained from the addition of one mole of HCl at high temperature to 1,3-butadiene?
Q5) Which of the following statements is incorrect about benzene?
A)All of the carbon atoms are sp hybridized.
B)It has delocalized electrons.
C)The carbon-carbon bond lengths are all the same.
D)The carbon-hydrogen bond lengths are all the same.
E)All twelve atoms lie in the same plane.
Q6) In the acetate ion (CH<sub>3</sub>CO<sub>2</sub><sup>-</sup>),which of the oxygen atoms bears a greater negative charge? Explain your answer. Page 11
Q7) Which MOs are bonding MOs in the ground state of 1,3,5-hexatriene?
Q8) Mark the most electron-rich carbon atom in the compound below with an asterisk.
To view all questions and flashcards with answers, click on the resource link above.
12
Chapter 9: Substitution and Elimination Reactions of Alkyl Halides
Available Study Resources on Quizplus for this Chatper
228 Verified Questions
228 Flashcards
Source URL: https://quizplus.com/quiz/73838
Sample Questions
Q1) Which of the following S<sub>N</sub>2 reactions is the slowest?
A)CH<sub>3</sub>CH<sub>2</sub>CHBrCH<sub>3</sub> + OH<sup>-</sup> CH<sub>3</sub>CH<sub>2</sub>CHOHCH<sub>3</sub> + Br<sup>-</sup>
B)CH<sub>3</sub>CH<sub>2</sub>CHBrCH<sub>3</sub> + H<sub>2</sub>O CH<sub>3</sub>CH<sub>2</sub>CHOHCH<sub>3</sub> + HBr
C)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br + OH<sup>-</sup> CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH + Br<sup>-</sup>
D)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br + H<sub>2</sub>O CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH + HBr
Q2) What is the major product which results when (2R,3S)-2-chloro-3-phenylbutane is treated with sodium methoxide in methanol?
A)(E)-2-phenyl-2-butene
B)(Z)-2-phenyl-2-butene
C)(S)-3-phenyl-1-butene
D)(R)-3-phenyl-1-butene
E)(R)-2-methoxy-2-phenylbutane
Q3) Why,in a polar protic solvent,is iodide a better nucleophile than fluoride?
Page 13
To view all questions and flashcards with answers, click on the resource link above.
Chapter 10: Reactions of Alcohols, ethers, epoxides, amines and
Sulfur-Containing Compounds
Available Study Resources on Quizplus for this Chatper
109 Verified Questions
109 Flashcards
Source URL: https://quizplus.com/quiz/73839
Sample Questions
Q1) Provide the structure of the major organic product which results when naphthalene oxide undergoes rearrangement in the presence of water.Explain the regioselectivity of this rearrangement.
Q2) Which of the following is the best method for preparing CH<sub>3</sub>Br?
A)CH<sub>3</sub>OH + Br<sup>-</sup>
B)CH<sub>3</sub>OH + HBr
C)CH<sub>3</sub>OH + Br<sub>2</sub>
D)CH<sub>3</sub>OH + NaBr
E)CH<sub>3</sub>OH + Br<sup>+</sup>
Q3) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
CH<sub>3</sub>(CH<sub>2</sub>)<sub>6</sub>CH<sub>2</sub>OH + HBr
Q4) When dipentyl ether is treated with excess HI,through what type of mechanism(s)does the major product result?
A)S<sub>N</sub>2
B)S<sub>N</sub>1
C)both S<sub>N</sub>1 and S<sub>N</sub>2
D)E1
E)E2
To view all questions and flashcards with answers, click on the resource link above. Page 14
Chapter 11: Organometallic Compounds
Available Study Resources on Quizplus for this Chatper
65 Verified Questions
65 Flashcards
Source URL: https://quizplus.com/quiz/73840
Sample Questions
Q1) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.
Q2) The following alkyl halide could not be used to form a Grignard reagent.Explain. HO-CH<sub>2</sub>CH<sub>2</sub>-Br
Q3) List the sequence of reagents necessary to prepare the appropriate Gilman reagent from ethyl iodide.
Q4) Which of the following sequences of reactions would be best when converting cyclohexene oxide into propylcyclohexane?
A)1)CH<sub>3</sub>CCNa 2.H<sub>3</sub>O<sup>+</sup> B)1)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgBr 2.H<sub>2</sub>SO<sub>4</sub>, 3.H<sub>2</sub>,Pt C)1)H<sub>3</sub>O<sup>+</sup> 2.CH<sub>3</sub>CCNa D)1)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Li 2.HBr E)1)H<sub>3</sub>PO<sub>4</sub>, 2.CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgBr 3.H<sup>+</sup>
Q5) Complete and balance the following transmetallation reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgCl + CdCl<sub>2</sub>
Q6) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Page 15
To view all questions and flashcards with answers, click on the resource link above.
Chapter 12: Radicals
Available Study Resources on Quizplus for this Chatper
141 Verified Questions
141 Flashcards
Source URL: https://quizplus.com/quiz/73841
Sample Questions
Q1) Name the two brominated products which result when 2,3-dimethyl-2-butene reacts with NBS.
Q2) Would chlorination or bromination of 2,5-dimethylhexane produce a greater yield of 1-halo-2,5-dimethylhexane?
Q3) Which of the following reactions is a termination step in the free radical chlorination of methane?
A)Cl<sub>2</sub> + Cl Cl + Cl<sub>2</sub>
B)Cl<sub>2</sub> 2 Cl
C) CH<sub>3</sub> + Cl CH<sub>3</sub>Cl
D)CH<sub>4</sub> + Cl HCl + CH<sub>3</sub>
Q4) Provide a series of synthetic steps by which (CH<sub>3</sub>)<sub>2</sub>C=CH<sub>2</sub> could be prepared from 2-methylpropane.
Q5) The reaction Br<sub>2</sub> + CH<sub>3</sub>Br CH<sub>2</sub>Br<sub>2</sub> + HBr was carried out.Which of the following mechanism steps is productive,but relatively unlikely to occur?
A)Br + CH<sub>3</sub>Br HBr + CH<sub>2</sub>Br
B)Br + CH<sub>2</sub>Br CH<sub>2</sub>Br<sub>2</sub>
C)Br + Br<sub>2</sub> Br<sub>2</sub> + Br
D)Br + CH<sub>3</sub> CH<sub>3</sub>Br
Page 16
To view all questions and flashcards with answers, click on the resource link above.
Chapter 13: Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy
Available Study Resources on Quizplus for this Chatper
140 Verified Questions
140 Flashcards
Source URL: https://quizplus.com/quiz/73842
Sample Questions
Q1) Which of the following compounds exhibits the pattern of m/z values shown below? 41,43,57,87,101,116
A)propylbromide
B)isopropyl bromide
C)sec-butyl isopropyl ether
D)2-hexanol
E)2-butanone
Q2) How could IR spectroscopy be used to distinguish between the following pair of compounds?
CH<sub>3</sub>OCH<sub>2</sub>CH<sub>3</sub> and CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
Q3) Give the m/z ratio that corresponds to the molecular ion in the mass spectrum of ethylpropylamine.
Q4) Deduce a possible structure for the compound with the IR absorptions below. C<sub>5</sub>H<sub>8</sub>O: 3000,1750 cm<sup>-1</sup>
Q5) Arrange the following regions of the electromagnetic spectrum in order of decreasing wavelength: microwaves,visible light,ultraviolet light,infrared radiation,X-rays.
To view all questions and flashcards with answers, click on the resource link above. Page 17
Q6) Explain how hydrogen bonding affects the shape of O-H and N-H absorption bands in IR spectra.
Chapter 14: Nmr Spectroscopy
Available Study Resources on Quizplus for this Chatper
122 Verified Questions
122 Flashcards
Source URL: https://quizplus.com/quiz/73843
Sample Questions
Q1) Deduce the identity of the following compound from the <sup>1</sup>H NMR spectral data given.
C<sub>3</sub>H<sub>3</sub>Cl<sub>5</sub> : 4.5 (1H,triplet),6.1 (2H,doublet)(ppm)
Q2) Describe the difference between a ketone and an aldehyde in the <sup>1</sup>H NMR spectrum.
A)An aldehyde has a signal at 9.0 - 10.0 ppm.
B)An aldehyde has a signal at 2.1 ppm.
C)An aldehyde has a signal at 5.0 ppm.
D)An aldehyde has a signal at 3.5 ppm.
E)An aldehyde has a signal at 8.0 ppm.
Q3) Deduce the structure from the data given: C<sub>7</sub>H<sub>16</sub>O; <sup>1</sup>H NMR (integration,coupling): 0.9 (9H,s),1.5 (2H,t),3.5 (3H,s),3.8 (2H,t).
Q4) Why is Fourier transform NMR spectroscopy preferred over continuous wave as a technique for <sup>13</sup>C NMR?
Q5) Deduce the identity of the following compound from the <sup>1</sup>H NMR spectral data given.
C<sub>6</sub>H<sub>8</sub>O<sub>4</sub> : 3.9 (6H,singlet),6.1 (2H,singlet)(ppm)
To view all questions and flashcards with answers, click on the resource link above.
Page 18
Chapter 15: Reactions of Carboxylic Acids and Carboxylic Acid
Derivatives
Available Study Resources on Quizplus for this Chatper
126 Verified Questions
126 Flashcards
Source URL: https://quizplus.com/quiz/73844
Sample Questions
Q1) Esters and amides are most easily made by nucleophilic acyl substitution reactions on
A)alcohols.
B)acid anhydrides.
C)carboxylates.
D)carboxylic acids.
E)acid chlorides.
Q2) Typically,amides will hydrolyze under ________ conditions than esters.
A)milder
B)more dilute
C)more vigorous
D)less vigorous
E)more saline
Q3) Which of the following is formed in the reaction between ethyl butanoate and ethyl amine?
A)ethanol
B)1-butanol
C)N-ethylbutanamide
D)both A and C
E)both B and C
To view all questions and flashcards with answers, click on the resource link above. Page 19
Chapter 16: Reactions of Aldehydes and Ketones
Available Study Resources on Quizplus for this Chatper
122 Verified Questions
122 Flashcards
Source URL: https://quizplus.com/quiz/73845
Sample Questions
Q1) Provide the major organic product which results when (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>COCl is treated with DIBAH.
Q2) Provide the major organic product of the reaction of aniline with 3-pentanone.
Q3) Which of the following amines will react with cyclopentanone to form an enamine?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>
B)(CH<sub>3</sub>)<sub>3</sub>N
C)pyridine
D)(CH<sub>3</sub>)<sub>3</sub>CNH<sub>2</sub>
E)none of the above
Q4) Which carbonyl is more susceptible to nucleophilic attack,that of cyclohexanone or that of hexanal? Provide two reasons for your choice.
Q5) What class of organic compounds results when cyclopentanone reacts with ethylamine in the presence of trace acid?
A)cyanohydrin
B)semicarbazone
C)imine
D)enamine
E)oxime
Q6) Provide the structure of the diethyl acetal of butanal.
To view all questions and flashcards with answers, click on the resource link above. Page 20
Chapter 17: Reactions at the -Carbon
Available Study Resources on Quizplus for this Chatper
121 Verified Questions
121 Flashcards
Source URL: https://quizplus.com/quiz/73846
Sample Questions
Q1) Which of the following compounds will give a positive iodoform test?
A)propanal
B)2-pentanone
C)3-pentanone
D)benzophenone
E)cyclohexanone
Q2) Provide a detailed,stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone,hydroxide and iodine.
Q3) In theory a poorly planned crossed aldol reaction can produce how many different aldol regioisomers?
A)1
B)2
C)3
D)4
E)5
Q4) Rank the following compounds in order of increasing acidity of their a-Hs,least acidic to most acidic: CH<sub>3</sub>CH<sub>2</sub>CON(CH<sub>3</sub>)<sub>2</sub>,PhCOCH<sub>2</ sub>CHO,CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3< /sub>,and PhCOCH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
To view all questions and flashcards with answers, click on the resource link above. Page 21
Chapter 18: Reactions of Benzene and Substituted
Benzenes
Available Study Resources on Quizplus for this Chatper
168 Verified Questions
168 Flashcards
Source URL: https://quizplus.com/quiz/73847
Sample Questions
Q1) What is the best method for the preparation of p-chlorotoluene in high yield?
A)start with benzene; methylate; chlorinate
B)start with benzene; chlorinate; methylate
C)start with toluene; chlorinate
D)start with chlorobenzene; methylate
E)start with p-aminotoluene; NaNO<sub>2</sub>/HCl,0°C; CuCl
Q2) Which of the following substituent on the benzene ring is a strong deactivator?
A)-<sup>+</sup>N(CH<sub>3</sub>)<sub>3</sub>
B)-<sup>+</sup>NH(CH<sub>3</sub>)<sub>2</sub>
C)-<sup>+</sup>NH<sub>2</sub>CH<sub>3</sub>
D)-NO<sub>2</sub>
E)all of the above
Q3) Sulfonation can be reversed
A)upon treatment with Zn/HCl.
B)upon treatment with chromic acid.
C)upon treatment with NBS.
D)in dilute acid at 100°C.
E)upon treatment with NaBH<sub>4</sub>.
Q4) Explain why nitrobenzene can be used as a solvent for Friedel-Crafts alkylation.
Page 22
Q5) Does cycloheptatriene have a higher or lower pKa than cyclopentadiene? Explain.
To view all questions and flashcards with answers, click on the resource link above.
Chapter 19: More About Amines - Reactions of Heterocylic Compounds
Available Study Resources on Quizplus for this Chatper
126 Verified Questions
126 Flashcards
Source URL: https://quizplus.com/quiz/73848
Sample Questions
Q1) Which of the following lists the correct order of reactivity of the substrates in electrophilic aromatic substitution reactions?
A)thiophene > pyrrole > furan > benzene
B)benzene > furan > thiophene > pyrrole
C)furan > pyrrole > benzene > thiophene
D)benzene > pyrrole > thiophene > furan
E)pyrrole > furan > thiophene > benzene
Q2) Draw 4-methylisoquinoline.
Q3) Draw the structure of piperidine.
Q4) Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.
Q5) Draw 2-methylpyrrolidine.
Q6) The lone pair in pyridine is present in a A)s-orbital.
B)p-orbital.
C)sp-orbital.
D)sp<sup>2</sup>-orbital.
E)sp<sup>3</sup>-orbital.
Q7) Pyridine does not undergo Friedel-Crafts reactions.Offer an explanation.
To view all questions and flashcards with answers, click on the resource link above. Page 23
Chapter 20: The Organic Chemistry of Carbohydrates
Available Study Resources on Quizplus for this Chatper
110 Verified Questions
110 Flashcards
Source URL: https://quizplus.com/quiz/73849
Sample Questions
Q1) An optically active D-aldopentose produced an optically inactive alditol upon treatment with NaBH<sub>4</sub>.When this aldopentose was subjected to a Ruff degradation,a D-aldotetrose was generated.This aldotetrose gave an optically active aldaric acid upon oxidation with HNO<sub>3</sub>.Use these data to provide the structure of the starting D-aldopentose.
Q2) Which of the following best represents the process of photosynthesis?
A)disproportionation
B)oxidation/reduction
C)exothermic
D)exergonic
E)elimination
Q3) Why is -D-glucopyranose more stable in nature than -D-glucopyranose?
Q4) Which of the following would give a positive Tollen's test?
A) -D-glucopyranose
B)methyl -D-glucopyranoside
C)sucrose
D)methyl -D-ribofuranoside
E)none of the above
Q5) What is the main structural difference between amylose and cellulose?
Q6) What nucleophilic carbon species is used in the Kiliani-Fischer synthesis?
To view all questions and flashcards with answers, click on the resource link above. Page 24
Chapter 21: Amino Acids,peptides,and Proteins
Available Study Resources on Quizplus for this Chatper
117 Verified Questions
117 Flashcards
Source URL: https://quizplus.com/quiz/73850
Sample Questions
Q1) The quaternary structure of proteins is concerned with which of the following?
A)sequence of amino acids in the peptide chain
B)description of the way the peptide chains are arranged with respect to each other
C)location of the disulfide bridges in the peptide chain
D)conformation of the protein backbone
E)three-dimensional arrangement of all atoms in the protein
Q2) Complete hydrolysis of a hexapeptide gives 2 Gly,Leu,Phe,Pro,and Tyr.Reaction of the peptide with phenylisothiocyanate gave the phenylthiohydantoin of Pro.Partial hydrolysis of the peptide gave the following fragments: Phe-Gly-Tyr,Gly-Phe-Gly,Pro-Leu-Gly,Leu-Gly-Phe.What is the structure of the peptide?
Q3) Draw the structure of the tetrapeptide Ser-Leu-Phe-Pro at pH 7.0.
Q4) Define what is meant by isoelectric point (pI)and give an example.
Q5) Which of the following amino acids has the highest isoelectric point?
A)arginine
B)aspartic acid
C)glycine
D)proline
E)phenylalanine
Q6) Explain the importance of the Merrifield method in peptide synthesis.
Page 25
To view all questions and flashcards with answers, click on the resource link above.
Chapter 22: Catalysis in Organic Reactions and in Enzymatic Reactions
Available Study Resources on Quizplus for this Chatper
92 Verified Questions
92 Flashcards
Source URL: https://quizplus.com/quiz/73851
Sample Questions
Q1) Give the first step of the mechanism for aldolase.
A)Fructose-1,6,-diphosphate forms an imine with a lysine residue at the active site of the enzyme.
B)A tyrosine residue functions as a base catalyst to cleave the bond between C-3 and C-4.
C)The enamine intermediate rearranges to an imine.
D)Hydrolysis of the imine releases dihydroxyacetone phosphate.
E)A molecule of glyceraldehyde-3-phosphate is expelled.
Q2) Describe the acid-catalyzed second slow step in the hydrolysis of an ester.
A)The electron pair on oxygen forms double bond and alcohol is the leaving group.
B)The base abstracts extra hydrogen from protonated alcohol.
C)The oxygen of the carbonyl group abstracts a hydrogen from HB.
D)Water attacks the carbonyl carbon and electron pair goes to oxygen.
E)The oxygen on the alkoxy group abstracts a hydrogen from HB.
Q3) Explain what is meant by the induced fit model.Give an example.
Q4) Explain the phenomenon known as molecular recognition.Give an example.
Q5) Why is histidine a versatile catalytic group?
Page 26
Q6) Explain what is meant by site-specific mutagenesis.
Q7) Provide the two general ways that metal ions catalyze organic reactions.
To view all questions and flashcards with answers, click on the resource link above.
Chapter 23: The Organic Chemistry of the Coenzymes, compounds
Derived From Vitamins
Available Study Resources on Quizplus for this Chatper
102 Verified Questions
102 Flashcards
Source URL: https://quizplus.com/quiz/73852
Sample Questions
Q1) Which of the following vitamins catalyzes acyl transfer reactions and requires CoASH as a coenzyme?
A)niacin
B)thiamine
C)vitamin B<sub>12</sub>
D)lipoate
E)panthothenate
Q2) Which of the following vitamins is needed for amino acid , -eliminations?
A)vitamin B<sub>12</sub>
B)vitamin B<sub>2</sub>
C)folic acid
D)vitamin B<sub>1</sub>
E)vitamin B<sub>6</sub>
Q3) Which of the following is/are coenzyme(s)formed from the vitamin niacin?
A)NAD<sup>+</sup>
B)NADP<sup>+</sup>
C)NADH
D)NADPH
E)all of the above
Q4) Give the purpose of biotin.
To view all questions and flashcards with answers, click on the resource link above. Page 27
Chapter 24: The Organic Chemistry of the Metabolic Pathways
Available Study Resources on Quizplus for this Chatper
90 Verified Questions
90 Flashcards
Source URL: https://quizplus.com/quiz/73853
Sample Questions
Q1) Describe what's happening mechanistically when glucose reacts with ATP to yield glucose-6-phosphate.
Q2) What organic compound is the most important form of chemical energy?
Q3) Acetyl-CoA enters the citric acid cycle by reacting with ________ to form ________.
Q4) How many citric acid cycles would be needed to produce nine molecules of FADH<sub>2</sub>?
A)nine citric acid cycles
B)one citric acid cycle
C)two citric acid cycles
D)four citric acid cycles
E)three citric acid cycles
Q5) Give the number of ATP molecules formed from NADH in the fourth stage of catabolism.
A)one
B)two
C)three
D)four
E)none
Q6) a-Ketoglutarate is an intermediate in the citric acid cycle.Draw its structure. Page 28
To view all questions and flashcards with answers, click on the resource link above. Page 29
Chapter 25: The Organic Chemistry of Lipids
Available Study Resources on Quizplus for this Chatper
37 Verified Questions
37 Flashcards
Source URL: https://quizplus.com/quiz/73854
Sample Questions
Q1) Identify the compound with the highest melting point.
A)palmitic acid
B)lauric acid
C)stearic acid
D)myristic acid
E)linoleic acid
Q2) What is the precursor of bile acids?
A)phosphoglyceride
B)acetyl CoA
C)squalene
D)prostaglandin
E)cholesterol
Q3) Which of the following statements is true about terpenes?
A)They are a class of lipids that can be isolated from plants.
B)They contain carbon atoms in multiples of five.
C)They are composed of isoprene units joined together in a head-to-tail fashion.
D)Tetraterpenes have 40 carbon atoms.
E)all of the above
Q4) Why do most naturally occurring fatty acids contain an even number of carbon atoms?
To view all questions and flashcards with answers, click on the resource link above.
Chapter 26: The Chemistry of the Nucleic Acids
Available Study Resources on Quizplus for this Chatper
94 Verified Questions
94 Flashcards
Source URL: https://quizplus.com/quiz/73855
Sample Questions
Q1) Which of the following explains the kinetic stability of ATP?
A)The hydrolysis of ATP occurs rapidly in the absence of a catalyst because the phosphate bonds are thermodynamically labile.
B)ATP is positively charged at physiological pH.
C)Water,the major component of cytoplasm,is a strong and very reactive nucleophile.
D)ATP is negatively charged at physiological pH and thus repels the approach of nucleophiles.
E)none of the above
Q2) For what compound is ATP an abbreviation?
A)adenine triphosphate
B)adenosine tetraphosphate
C)adenine tetraphosphate
D)adenosine triphosphate
E)adenine triphosphoric acid
Q3) What is a nucleotide? Give an example.
Q4) Draw the structure of ADP.
Q5) Show that you understand how the structural components of DNA are bonded together by drawing a linear segment that contains 3 base residues.
To view all questions and flashcards with answers, click on the resource link above. Page 31
Chapter 27: Synthetic Polymers
Available Study Resources on Quizplus for this Chatper
116 Verified Questions
116 Flashcards
Source URL: https://quizplus.com/quiz/73856
Sample Questions
Q1) Draw the structure of Nylon 66.
Q2) Show the mechanism for the formation of a segment of polystyrene containing two molecules of styrene and initiated by hydrogen peroxide.
Q3) Draw a short segment of neoprene,using four monomers.
Q4) List the two major classes of synthetic polymers and give one example of each.
Q5) List the two main groups of polymers and give one example of each.
Q6) Which of the following can result in chain termination in cationic polymerization?
A)loss of H+
B)addition of a nucleophile that reacts with the propagating site
C)a chain transfer reaction with the solvent
D)a 1,2-hydride shift.
E)A,B,and C
Q7) Identify the monomer(s)that undergo radical polymerization.You may choose more than one answer.
A)styrene
B)methyl methacrylate
C)vinyl chloride
D)methyl vinyl ether
E)acrylamide
Page 32
To view all questions and flashcards with answers, click on the resource link above.
Chapter 28: Pericyclic Reactions
Available Study Resources on Quizplus for this Chatper
102 Verified Questions
102 Flashcards
Source URL: https://quizplus.com/quiz/73857
Sample Questions
Q1) What does LCAO stand for?
Q2) Describe a cycloaddition reaction.
A)The reactant has lost a sigma bond,the product has a new sigma bond,and the pi bonds have rearranged.
B)The product contains a new ring,with two less sigma bonds,and two more pi bonds than the starting material.
C)The product contains a new ring,with two more sigma bonds,and two less pi bonds than the starting material.
D)The product contains a new ring,with one less sigma bond,and one more pi bond than the starting material.
E)The product contains a new ring,with one more sigma bond,and one less pi bond than the starting material.
Q3) Which molecular orbital is higher in energy: the in-phase or out-of-phase overlap of atomic orbitals?
Q4) What characterizes a pericyclic reaction?
Q5) What is meant by frontier orbitals?
Q6) Explain what a node is and how it is formed.
Q7) Under thermal conditions,is an [8+2] cycloaddition suprafacial or antarafacial?
To view all questions and flashcards with answers, click on the resource link above. Page 33
Q8) Give a representation of the antibonding molecular orbital of the allyl anion.