Chemical Incompatibility, Acid-Base Reactions, and Hydrolysis/Solvolysis

​Q: According to the Arrhenius Definition, a substance is considered a base if it dissolves in water to produce which ion?
A) Hydronium (\text{H}_3\text{O}^+) ions B) Chloride (\text{Cl}^-) ions C) Hydroxide (\text{OH}^-) ions D) Proton (\text{H}^+) ions

C The Arrhenius definition states that a base is a substance that dissolves in water to produce hydroxide (\text{OH}^-) ions.

​Q: The Brønsted-Lowry Definition of acid-base reactions focuses on the transfer of which particle?
A) Electron B) Neutron C) Proton (\text{H}^+ ion) D) Hydroxide ion (\text{OH}^-)

C The Brønsted-Lowry definition defines acid-base reactions in terms of the transfer of a proton (\text{H}^+ ion) from one substance (acid) to another (base).

​Q: Which type of acid is defined as one that partially donates protons (\text{H}^+)?
A) Strong acid B) Conjugate acid C) Weak acid D) Monoprotic acid

C A weak acid, under the Brønsted-Lowry definition, is one that partially donates or dissociates its protons (\text{H}^+).

​Q: How does the Arrhenius definition differ from the Brønsted-Lowry definition in terms of focus?
A) Arrhenius focuses on all solvents, while Brønsted-Lowry focuses only on water. B) Arrhenius focuses only on \text{H}^+ and \text{OH}^- ions in water. C) Arrhenius focuses on electron pair transfer. D) Arrhenius focuses on gas formation in reactions.

B The Arrhenius definition is limited as it "Focuses only on \text{H}^+ and \text{OH}^- ions in water," while the Brønsted-Lowry definition is broader, focusing on proton transfer regardless of the solvent (though water is a common one).

​Q: Which property is characteristic of a base?
A) Sour taste B) Turns blue litmus paper red C) Slippery to the touch D) Dissolves carbonate salts

C Bases are known to be "Slippery to the touch," while the other options describe acids.

​Q: An acid's ability to dissolve carbonate salts and release \text{CO}_2 is related to its:
A) Proton-accepting ability B) Tendency to produce \text{H}^+ in water C) Bitter taste D) Ability to form precipitates

B Acids are substances that produce \text{H}^+ in water, and one of their characteristics is that they dissolve carbonate salts, releasing \text{CO}_2.

​Q: Acetic acid (\text{CH}3\text{CO}2\text{H}) is an example of a monoprotic acid because it has:
A) The ability to accept only one proton. B) A single -\text{CO}_2\text{H} group that dissociates to form one \text{H}^+. C) A sour taste. D) A high boiling point.

B Monoprotic acids like acetic acid have a single -\text{CO}_2\text{H} group and can only donate one proton (\text{H}^+) per molecule.

​Q: Which term describes a compound that can donate more than one proton (\text{H}^+) per molecule?
A) Monoprotic Acid B) Polyprotic Acid C) Monobasic Acid D) Conjugate Base

B A compound capable of donating more than one proton per molecule is classified as a polyprotic acid.

​Q: What taste is characteristically associated with an acid?
A) Sweet B) Umami C) Bitter D) Sour

D Acids are generally characterized by a "Sour taste."

​Q: The equation \text{Ca}(\text{OH})2 + \text{CO}2 \to \text{CaCO}3 + \text{H}2\text{O} is an example of an acid-base reaction leading to what observable result?
A) Evolution of Gas B) Color Change C) Precipitation D) Solvolysis

C The reaction produces calcium carbonate (\text{CaCO}_3), which is a solid precipitate, indicating a precipitation reaction.

​Q: A substance that turns blue litmus paper red and is a proton (\text{H}^+) donor is likely a(n):
A) Weak base B) Strong base C) Acid D) Neutral salt

C Acids turn blue litmus paper red and, according to Brønsted-Lowry, are proton donors.

​Q: Which of the following is NOT listed as a possible consequence that may arise from acid-base reactions?
A) Precipitation B) Drug degradation C) Gas formation D) Color change

B The text lists Precipitation, Gas formation, and Color change as results of acid-base reactions, but drug degradation is more related to hydrolysis or incompatibility.

​Q: Which acid is an example of a monoprotic mineral acid?
A) Sulfuric acid (\text{H}2\text{SO}4) B) Phosphoric acid (\text{H}3\text{PO}4) C) Hydrochloric acid (\text{HCl}) D) Carbonic acid (\text{H}2\text{CO}3)

C \text{HCl} (hydrochloric acid) is listed among the monoprotic acids, while the others are polyprotic.

​Q: Weak bases are defined as substances that:
A) Fully accept protons (\text{H}^+). B) Fully donate protons (\text{H}^+). C) Partially accept protons (\text{H}^+). D) Produce \text{H}^+ ions in water.

C A weak base is defined by the Brønsted-Lowry definition as one that "Partially accepts protons (\text{H}^+)."

​Q: What is the main characteristic of an acid-base reaction that facilitates effervescence?
A) Precipitation B) Evolution of Gas C) Color Change D) Hydrolysis

B Effervescence is the bubbling or fizzing resulting from the "Evolution of Gas" during a reaction.

​Hydrolysis: Principles and Types (Items 16-30)
​Q: Hydrolysis is described as the most common type of incompatibility and involves the decomposition of a substance in the presence of what?
A) Alcohol B) Heat C) Light D) Water

D Hydrolysis involves the decomposition or breakdown of a substance "in the presence of water."

​Q: Which of the following functional groups is susceptible to hydrolysis?
A) Alkanes B) Lactams C) Ethers D) Aromatic Rings

B Lactams (found in Penicillins, Cephalosporins) are explicitly listed as a functional group susceptible to hydrolysis.

​Q: The \text{pH} is a critical factor that induces hydrolysis. For Atropine, what is the optimal \text{pH} range for stability?
A) 6.0-7.0 B) 3.1-4.5 C) 1.0-2.0 D) 7.5-8.5

B The optimal \text{pH} for Atropine is given as 3.1-4.5, illustrating how \text{pH} affects stability and hydrolysis.

​Q: The process of autoclave sterilization can induce hydrolysis because it involves which factor?
A) Low \text{pH} B) Absence of water C) High temperature D) Light exposure

C High temperature, which is characteristic of the autoclave process, is listed as a factor that induces hydrolysis.

​Q: In Ionic Hydrolysis, the compound is broken into ions by water, and the bond broken between the ions is:
A) Ionic bond B) Covalent bond C) Metallic bond D) Hydrogen bond

B Ionic Hydrolysis involves the breaking of the "Covalent bond between ions of compound."

​Q: Which of the following characteristics is true for Ionic Hydrolysis?
A) It is generally an irreversible process. B) It most affects weak bases and salts. C) It is a slow, molecular breakdown. D) It must be avoided at all costs.

B Ionic Hydrolysis is characterized as reversible and "Most affected are weak bases and salts."

​Q: Molecular Hydrolysis is described as a process that is:
A) Fast and reversible. B) Slow and reversible. C) Slow and irreversible. D) Fast and ionic.

C Molecular Hydrolysis is characterized as a "Slow process and irreversible."

​Q: The breakdown of Acetylsalicylic acid into Salicylic acid and Acetic acid is an example of which type of hydrolysis?
A) Ionic Hydrolysis B) Acid-Base Reaction C) Molecular Hydrolysis D) Solvolysis

C This decomposition of the molecule itself is given as the specific example of Molecular Hydrolysis.

​Q: Amides are a group susceptible to hydrolysis. They are commonly found in which class of drugs?
A) Tetracycline antibiotics B) Local anesthetics C) ACE Inhibitors D) Nitrates

B Amides (along with Esters) are listed as susceptible groups found in "Local anesthetics."

​Q: The process where Codeine phosphate reversibly breaks down into Codeine and Phosphate is an example used to illustrate:
A) Molecular Hydrolysis B) Solvolysis C) Ionic Hydrolysis D) Precipitation

C This is the specific example provided for the reversible nature of Ionic Hydrolysis.

​Q: The key difference between Ionic Hydrolysis and Molecular Hydrolysis is that Molecular Hydrolysis is irreversible and:
A) Affects only strong acids. B) Involves the molecule itself being broken down. C) Requires an alcohol solvent. D) Is always a fast reaction.

B Molecular Hydrolysis involves the "Molecule itself is broken down," distinguishing it from Ionic Hydrolysis where a covalent bond between ions is broken.

​Q: If a pharmaceutical formulation contains an ester functional group, it is chemically susceptible to:
A) Effervescence B) \text{CO}_2 release C) Hydrolysis D) Color change

C Esters are listed as one of the functional groups susceptible to hydrolysis (decomposition by water).

​Q: Why is the effervescence resulting from gas formation often desired in pharmaceutical formulations?
A) To increase the drug's shelf life B) To mask salty and bitter-tasting drugs C) To prevent precipitation D) To slow down the hydrolysis rate

B Effervescence is desired in reactions because it helps "to mask salty and bitter-tasting drugs."

​Q: The incompatibility between Antacids and Tetracycline Antibiotics is given as a real-world example of which type of reaction/interaction?
A) Molecular Hydrolysis B) Solvolysis C) Acid-Base Reactions D) Plasma Esterase Interaction

C The text lists this as an "Example 1" under "Real-World Examples" for Acid-Base Reactions.

​Q: Which of the following is NOT listed as a factor that induces or accelerates the process of hydrolysis?
A) Presence of water B) Low temperature C) \text{pH} D) High temperature

B High temperature is a factor, but low temperature would generally slow down the rate of hydrolysis, not induce it.

​Hydrolysis Drug Interactions and Solvolysis (Items 31-45)
​Q: The prodrug Enalapril requires hydrolysis by which enzymes to form the active compound enalaprilat?
A) Pseudo-cholinesterases B) Plasma esterases C) Liver esterases D) Hydrolases

C Enalapril is an inactive prodrug that requires hydrolysis by "liver esterases" to become the active drug enalaprilat.

​Q: Patients with a genetic deficiency in plasma pseudocholinesterases who are administered Procaine may experience:
A) Reduced drug efficacy B) Reduced rate of hydrolysis C) Prolonged anesthesia and potential toxicity D) Rapid metabolism and short duration of action

C Since Procaine is rapidly hydrolyzed by these enzymes, a deficiency leads to a slower breakdown, resulting in "prolonged anesthesia and potential toxicity."

​Q: What is the primary functional consequence of liver disease on the hydrolysis of the prodrug Enalapril?
A) Increased \text{pH} of the stomach, promoting degradation B) Impairment of hydrolysis, reducing antihypertensive effectiveness C) Faster conversion to the active form, increasing toxicity D) Enhanced absorption in the gastrointestinal tract

B Liver disease can impair the hydrolysis by liver esterases, thereby "reducing the drug's antihypertensive effectiveness."

​Q: Solvolysis is a chemical reaction in which the solvent acts as or produces:
A) Strong acids B) Electron-rich nucleophiles C) Transition metals D) Stable ionic compounds

B Solvents act as or produce "electron-rich atoms or groups of atoms (nucleophiles)" that participate in the reaction.

​Q: Besides water, which pharmaceutical co-solvents can act as nucleophiles and participate in solvolysis reactions?
A) Tincture of iodine B) Polyethylene glycol or ethyl alcohol C) Carbon dioxide D) Mineral oil

B The text specifically mentions "ethyl alcohol or polyethylene glycol" as pharmaceutical co-solvents that can be involved in solvolysis.

​Q: The most common solvolysis reactions in pharmaceuticals involve "labile" carbonyl compounds such as:
A) Alkenes and alkynes B) Amines and sulfides C) Esters, lactones, and lactams D) Phenols and thiols

C The text states that the most common solvolysis reactions involve "labile" carbonyl compounds such as "esters, lactones, and lactams."

​Q: In the solvolysis of Chloramphenicol palmitate (pediatric suspension), what environment promotes hydrolysis to the active Chloramphenicol?
A) Lipophilic environments B) High \text{pH} C) Aqueous conditions D) Alcohol-rich solutions

C "Aqueous conditions promote hydrolysis to active chloramphenicol," while lipophilic environments slow it down.

​Q: Benzylpenicillin (\text{Penicillin G}) degradation is an example of solvolysis involving the opening of the:
A) Pyrimidine ring B) \text{CO}_2\text{H} group C) \beta-lactam ring D) Benzene ring

C Penicillin G's degradation via solvolysis involves the "\beta-lactam ring opening."

​Q: Why do penicillin suspensions typically have limited shelf life and specific storage requirements?
A) Their bitter taste degrades quickly. B) They are highly susceptible to solvolysis in aqueous solutions. C) They are sensitive to light and heat only. D) They rapidly precipitate at room temperature.

B Their susceptibility to solvolysis (\beta-lactam ring opening) in aqueous solutions limits their shelf life.

​Q: The solvolysis of Nitroglycerin tablets when exposed to moisture or certain solvents leads to a reduction in the medication's:
A) Shelf life and stability B) Particle size C) Vasodilatory effectiveness D) Oral absorption rate

C This degradation reduces the drug's ability to perform its function, thereby reducing its "vasodilatory effectiveness."

​Q: Solvents involved in solvolysis can act as eliminating agents at high temperatures or in the presence of strong bases, producing which type of compound from alkyl halides?
A) Alkanes B) Alkyl ethers C) Alkenes D) Alcohols

C The text notes that some solvents can act as eliminating agents, "producing alkenes from alkyl halides."

​Q: In solvolysis, the active drug undergoes decomposition following a reaction with:
A) Atmospheric oxygen B) The container material C) The solvent present D) Trace heavy metals

C The definition states that in solvolysis, the active drug undergoes decomposition "following reaction with the solvent present."

​Q: \text{Procaine} is hydrolyzed into para-aminobenzoic acid and:
A) Salicylic acid B) \text{CO}_2 C) Diethylaminoethanol D) Enalaprilat

C The example specifies the products of Procaine hydrolysis are para-aminobenzoic acid + diethylaminoethanol.

​Q: Which type of solvent environment may slow down the conversion of Chloramphenicol palmitate to its active form, affecting bioavailability?
A) Highly acidic conditions B) Lipophilic environments C) Alcohol-rich environments D) Aqueous conditions

B The rate of solvolysis depends on the environment; "lipophilic environments may slow this conversion."

​Q: The ACE Inhibitor Enalapril is an example of a drug interaction that highlights the importance of the liver's role in drug:
A) Precipitation B) Proton transfer C) Hydrolysis/Activation D) Solvolysis in alcohol

C The example focuses on Enalapril's requirement for hydrolysis by liver esterases for activation.

​Synthesis and Advanced Concepts (Items 46-60)
​Q: If an acid is classified as a polyprotic acid, which property will it exhibit?
A) It will turn red litmus paper blue. B) It can donate \text{H}^+ ions on a one-to-one molar basis. C) It has multiple \text{H}^+ ions available for donation. D) It is only stable in non-aqueous solvents.

C A polyprotic acid can donate "more than one proton" per molecule, meaning it has multiple \text{H}^+ ions available.

​Q: The goal of facilitating effervescence in a liquid drug formulation is a practical application of which chemical principle?
A) Precipitation reaction B) Hydrolysis of an ester C) Gas-forming acid-base reaction D) Ionic solvolysis

C Effervescence is caused by the "Evolution of Gas," which is a result of certain acid-base reactions.

​Q: Why is Molecular Hydrolysis described with the phrase "It must be avoided" in pharmaceutical development?
A) It is reversible, making it hard to control. B) It is irreversible and leads to the breakdown of the active drug molecule itself. C) It is only a problem at low temperatures. D) It only affects inactive prodrugs.

B Since it is irreversible and breaks down the active drug molecule (e.g., Acetylsalicylic acid), its occurrence in a formulation is highly undesirable.

​Q: A pharmaceutical compound contains a lactam group. If stored improperly in a warm, aqueous environment, it is most likely to undergo:
A) Color change B) Precipitation C) Solvolysis/Hydrolysis D) Simple acid-base neutralization

C Lactams are listed as one of the groups highly susceptible to hydrolysis (a form of solvolysis) in the presence of water and high temperature.

​Q: Which of the following drugs represents a chemical challenge due to its use as an inactive prodrug requiring hydrolysis for activation?
A) Procaine B) Acetylsalicylic acid C) Enalapril D) Codeine

C Enalapril is specifically given as the example of an inactive prodrug that requires hydrolysis by liver esterases to become active.

​Q: The use of an antacid along with a tetracycline antibiotic can lead to reduced efficacy of the antibiotic. This is primarily a consequence of:
A) Solvolysis by alcohol B) Altered \text{pH} impacting drug solubility/absorption C) Molecular hydrolysis D) Genetic enzyme deficiency

B Antacids are bases that can neutralize stomach acid. This \text{pH} change can affect the solubility and absorption of the tetracycline, an example of acid-base incompatibility.

​Q: In Ionic Hydrolysis, the most affected compounds are weak bases and salts. What is the key chemical feature that makes this hydrolysis reversible?
A) The molecule itself is broken down. B) It does not require water. C) It involves the establishment of an equilibrium between the ions and the original compound. D) It is a very slow process.

C The example (\text{Codeine phosphate} \leftrightarrow \text{Codeine} + \text{Phosphate}) shows the reaction is in equilibrium, meaning it is reversible due to the ions and the original compound re-forming.

​Q: Which scientist is credited as the first to define acids and bases in detail, focusing on \text{H}^+ and \text{OH}^- ions in water?
A) T. M. Lowry B) Svante Arrhenius C) J. N. Brønsted D) Codeine phosphate

B The text identifies Svante Arrhenius as the first person to define acids and bases in detail using the \text{H}^+ and \text{OH}^- ion concept in water.

​Q: A solvent acting as a nucleophile and attacking an electropositive center in a drug molecule is the defining characteristic of what type of decomposition reaction?
A) Precipitation B) Effervescence C) Solvolysis D) Neutralization

C Solvolysis is characterized by the solvent acting as a nucleophile and displacing a group in the substrate molecule.

​Q: The fact that Benzylpenicillin is highly susceptible to solvolysis in aqueous solutions and has a limited shelf life is directly due to the chemical instability of its:
A) Carboxylic acid group B) \beta-lactam ring C) Phenyl group D) Alkyl halide moiety

B The \beta-lactam ring is a "labile" carbonyl compound (lactam) that readily undergoes ring opening (decomposition) via solvolysis.

​Q: If a liquid pharmaceutical preparation exhibits a cloudiness and the formation of visible particles after several weeks of storage, the most likely form of incompatibility is:
A) Evolution of Gas B) Color Change C) Hydrolysis D) Precipitation

D "Precipitation" involves the "separation of a solid" and the formation of a new substance, which would appear as cloudiness or visible particles.

​Q: The requirement for a drug to undergo hydrolysis by plasma esterases (like Procaine) or liver esterases (like Enalapril) primarily involves the breakdown of which susceptible functional group?
A) Amides/Esters B) Lactams C) Imines D) Alkenes

A Both examples involve the action of esterases on a drug, which are enzymes that break down ester (\text{Procaine}) and amide (\text{Enalapril} is an ester prodrug of an amide-containing active drug \text{enalaprilat}) functional groups via hydrolysis.

​Q: The transfer of a proton (\text{H}^+) is central to which acid-base theory?
A) Arrhenius Definition B) Brønsted-Lowry Definition C) Lewis Definition D) Svante Theory

B The Brønsted-Lowry definition defines acid-base reactions "in terms of the transfer of a proton (\text{H}^+ ion) from one substance to another."

​Q: A monoprotic acid like \text{HI} (Hydroiodic acid) dissociates to form \text{I}^- and \text{H}^+. If the acid is weak, what chemical feature is true about the final solution?
A) The solution will not conduct electricity. B) The \text{H}^+ concentration will be equal to the initial acid concentration. C) Most of the \text{H}^+ will remain bound to the \text{I}^-. D) It will turn red litmus paper blue.

C A weak acid "Partially donates protons," meaning that a significant portion of the acid molecules will remain undissociated, and most of the \text{H}^+ will remain bound to the counterion.

​Q: Which factor is generally considered the most common reason for the chemical incompatibility and degradation of pharmaceutical liquids and solutions?
A) Gas formation B) Solvolysis by co-solvents C) Hydrolysis (decomposition in water) D) Precipitation

C Hydrolysis is explicitly stated as the "Most common type of incompatibility," involving the breakdown of a substance in the presence of water.