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Oxalic acid, systematically named ethanedioic acid, represents the simplest member of the dicarboxylic acid class.
Answer: True
Explanation: Oxalic acid, with the chemical formula H₂C₂O₄, is systematically designated as ethanedioic acid, marking it as the simplest dicarboxylic acid.
Oxalic acid exhibits a lower acidity compared to acetic acid.
Answer: False
Explanation: Oxalic acid is significantly stronger as an acid when compared to acetic acid.
The conjugate bases of oxalic acid, hydrogen oxalate and oxalate, function as chelating agents.
Answer: True
Explanation: The conjugate bases of oxalic acid, hydrogen oxalate and oxalate, are known to act as chelating agents, capable of binding to metal ions.
The most common form of oxalic acid found is the anhydrous form.
Answer: False
Explanation: The dihydrate form (H₂C₂O₄·2H₂O) is the most commonly encountered form of oxalic acid, rather than the anhydrous form.
Anhydrous oxalic acid exists in two polymorphs, distinguished by differences in molecular arrangement and hydrogen bonding patterns.
Answer: True
Explanation: Anhydrous oxalic acid manifests in two distinct crystalline forms, known as polymorphs, differentiated by their molecular packing and hydrogen bonding configurations.
The chemical formula for oxalic acid dihydrate is H₂C₂O₄·H₂O.
Answer: False
Explanation: The chemical formula for the dihydrate form of oxalic acid is H₂C₂O₄·2H₂O, not H₂C₂O₄·H₂O.
Oxalic acid has two pKa values, approximately 1.25 and 4.28, indicating it is a diprotic acid.
Answer: True
Explanation: The pKa values for oxalic acid are approximately 1.25 and 4.28, confirming its nature as a diprotic acid.
Oxalic acid is considered a weak acid, comparable in strength to many aliphatic carboxylic acids.
Answer: False
Explanation: Oxalic acid is classified as a relatively strong acid, particularly when contrasted with numerous other common carboxylic acids.
Oxalyl chloride is a derivative of oxalic acid where the hydroxyl groups are replaced by chlorine atoms.
Answer: True
Explanation: Oxalyl chloride is identified as the acid chloride derivative of oxalic acid, meaning its hydroxyl groups have been substituted with chlorine atoms.
When heated between 125-175°C, oxalic acid vapor decomposes into carbon monoxide and formic acid.
Answer: False
Explanation: Upon thermal treatment between 125-175°C, oxalic acid vapor decomposes into carbon dioxide (CO₂) and formic acid (HCOOH), not carbon monoxide.
The standard state condition for data presented in the infobox is typically 0°C and 100 kPa.
Answer: False
Explanation: Data presented in infoboxes typically pertains to materials in their standard state, defined as 25°C (77°F) and 100 kPa, not 0°C.
The chemical formula for the dihydrate form of oxalic acid is H₂C₂O₄·2H₂O.
Answer: True
Explanation: The dihydrate form of oxalic acid is represented by the chemical formula H₂C₂O₄·2H₂O.
What is the IUPAC name for oxalic acid, the simplest dicarboxylic acid?
Answer: Ethanedioic acid
Explanation: Oxalic acid, with the chemical formula H₂C₂O₄, is systematically designated as ethanedioic acid, marking it as the simplest dicarboxylic acid.
How does the acidity of oxalic acid compare to that of acetic acid?
Answer: Oxalic acid is significantly stronger than acetic acid.
Explanation: Oxalic acid exhibits significantly greater acidity when compared to acetic acid.
What is the primary function of the conjugate bases of oxalic acid, hydrogen oxalate and oxalate?
Answer: Acting as chelating agents
Explanation: The conjugate bases of oxalic acid, namely hydrogen oxalate and oxalate, function as chelating agents, capable of forming coordinate bonds with metal cations.
What is the typical hydrated form of oxalic acid?
Answer: Dihydrate (H₂C₂O₄·2H₂O)
Explanation: The prevalent form of oxalic acid encountered is the dihydrate, characterized by the chemical formula H₂C₂O₄·2H₂O.
How are the two polymorphs of anhydrous oxalic acid distinguished?
Answer: By molecular arrangement and hydrogen bonding.
Explanation: Anhydrous oxalic acid manifests in two distinct crystalline forms, known as polymorphs, differentiated by their molecular packing and hydrogen bonding configurations.
What are the approximate pKa values for the two dissociations of oxalic acid?
Answer: 1.25 and 4.28
Explanation: Literature values for the pKa of oxalic acid typically indicate approximately 1.25 for the first proton dissociation and 4.28 for the second.
Oxalyl chloride is described in the source as a derivative of oxalic acid where:
Answer: The hydroxyl groups are replaced by chlorine atoms.
Explanation: Oxalyl chloride is identified as the acid chloride derivative of oxalic acid, meaning its hydroxyl groups have been substituted with chlorine atoms.
Upon thermal decomposition between 125-175°C, oxalic acid vapor decomposes into which two products?
Answer: Carbon dioxide and formic acid
Explanation: Upon thermal treatment between 125-175°C, oxalic acid vapor undergoes decomposition, yielding carbon dioxide (CO₂) and formic acid (HCOOH).
Historically, oxalic acid was first isolated from plants belonging to the genus *Rosa*.
Answer: False
Explanation: The historical isolation of oxalic acid was from plants of the genus *Oxalis*, not *Rosa*.
In 1773, Carl Wilhelm Scheele isolated oxalic acid from wood sorrel.
Answer: False
Explanation: While Carl Wilhelm Scheele was a key figure in oxalic acid research, the initial isolation from wood sorrel in 1773 is attributed to François Pierre Savary.
Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman produced oxalic acid in 1776 by reacting sugar with concentrated nitric acid.
Answer: True
Explanation: In 1776, Carl Wilhelm Scheele and Torbern Olof Bergman successfully synthesized oxalic acid through the reaction of sugar with concentrated nitric acid.
Carl Wilhelm Scheele initially named the acid he produced from sugar 'oxalic acid'.
Answer: False
Explanation: Carl Wilhelm Scheele initially referred to the acid derived from sugar as 'socker-syra', translating to 'sugar acid', not 'oxalic acid'.
The modern name 'oxalic acid' was established in the late 18th century by Antoine Lavoisier and his colleagues.
Answer: True
Explanation: The contemporary nomenclature 'oxalic acid' was established in 1787 by Louis-Bernard Guyton de Morveau, Antoine Lavoisier, and their collaborators during a significant revision of chemical terminology.
Friedrich Wöhler's 1824 synthesis of oxalic acid from cyanogen and ammonia is considered a landmark achievement in organic chemistry.
Answer: True
Explanation: Friedrich Wöhler's 1824 synthesis of oxalic acid via the reaction of cyanogen with ammonia is recognized as a potentially seminal achievement, marking one of the first instances of synthesizing a naturally occurring compound.
From which genus of plants was oxalic acid historically isolated?
Answer: Oxalis
Explanation: The historical isolation of oxalic acid was from plants of the genus *Oxalis*, commonly known as wood-sorrels.
Who first isolated oxalic acid from its salt found in wood sorrel in 1773?
Answer: François Pierre Savary
Explanation: In 1773, François Pierre Savary, a botanist and physician, successfully isolated oxalic acid from its salt derived from wood sorrel.
What substance did Carl Wilhelm Scheele and Torbern Olof Bergman use to produce oxalic acid in 1776?
Answer: Sugar
Explanation: In 1776, Carl Wilhelm Scheele and Torbern Olof Bergman successfully synthesized oxalic acid through the reaction of sugar with concentrated nitric acid.
What did Scheele initially call the acid he produced from sugar?
Answer: Socker-syra
Explanation: Carl Wilhelm Scheele initially designated the acid derived from sugar as 'socker-syra' (or 'säcker-syra'), a term translating to 'sugar acid'.
Which group is credited with introducing the modern name 'oxalic acid' in 1787?
Answer: Guyton de Morveau, Lavoisier, and co-authors
Explanation: The contemporary nomenclature 'oxalic acid' was established in 1787 by Louis-Bernard Guyton de Morveau, Antoine Lavoisier, and their collaborators during a significant revision of chemical terminology.
Friedrich Wöhler's 1824 experiment involving cyanogen and ammonia is significant because it was potentially the:
Answer: First synthesis of a naturally occurring compound.
Explanation: Friedrich Wöhler's 1824 synthesis of oxalic acid via the reaction of cyanogen with ammonia is recognized as a potentially seminal achievement, marking one of the first instances of synthesizing a naturally occurring compound.
The primary industrial method for producing oxalic acid involves the reduction of carbohydrates using sulfuric acid.
Answer: False
Explanation: The primary industrial method involves the oxidation of carbohydrates, not their reduction, typically using nitric acid or air.
A newer industrial process for oxalic acid involves creating diesters of oxalic acid from alcohols, followed by hydrolysis.
Answer: True
Explanation: A contemporary industrial approach entails the oxidative carbonylation of alcohols, yielding diesters of oxalic acid, which are subsequently hydrolyzed to produce the target compound.
Historically, oxalic acid was obtained by treating sawdust with strong acids like sulfuric acid.
Answer: False
Explanation: Historically, oxalic acid was obtained by treating sawdust with strong bases, followed by acidification, not directly with strong acids.
In a laboratory setting, oxalic acid can be synthesized by oxidizing sucrose using nitric acid with a vanadium pentoxide catalyst.
Answer: True
Explanation: Laboratory synthesis of oxalic acid can be achieved via the oxidation of sucrose employing nitric acid, often in the presence of a catalytic quantity of vanadium pentoxide.
Which of the following is a primary method for the industrial production of oxalic acid?
Answer: Oxidation of carbohydrates using nitric acid or air.
Explanation: The principal industrial methodologies for oxalic acid production involve the oxidation of carbohydrates, such as glucose, frequently employing nitric acid or atmospheric oxygen as oxidants.
What historical method was used to obtain oxalic acid from sawdust?
Answer: Treating with strong bases followed by acidification.
Explanation: Historically, oxalic acid was procured through the treatment of sawdust with potent bases (e.g., sodium hydroxide), followed by the acidification of the resultant oxalate salts using mineral acids.
A primary use of oxalic acid is in removing rust due to its ability to form a water-soluble complex with ferric iron.
Answer: True
Explanation: Oxalic acid is effectively employed for rust removal, leveraging its capacity to form a water-soluble complex with ferric iron.
Oxalic acid aids in leaching manganese from ores by oxidizing manganese dioxide into a soluble form.
Answer: False
Explanation: Oxalic acid facilitates manganese leaching by acting as a reducing agent, converting manganese dioxide into a soluble form, rather than oxidizing it.
In lanthanide chemistry, oxalic acid is used because it forms insoluble lanthanide oxalates that are difficult to filter and purify.
Answer: False
Explanation: Oxalic acid is used in lanthanide chemistry because it forms precipitates of lanthanide oxalates that are crystalline, easily filtered, and largely free from contamination, facilitating purification.
Oxalic acid is the main active ingredient in the cleaning product Bar Keepers Friend.
Answer: True
Explanation: Oxalic acid functions as the principal active agent in the widely recognized cleaning formulation, Bar Keepers Friend.
Approximately 25% of globally produced oxalic acid is used as a mordant in dyeing processes.
Answer: True
Explanation: An estimated 25% of the global production volume of oxalic acid is allocated to its application as a mordant in textile dyeing processes.
In aluminum anodizing, coatings made with oxalic acid are typically thicker and rougher than those made with sulfuric acid.
Answer: False
Explanation: In aluminum anodizing applications, oxalic acid yields coatings that are characterized by reduced thickness and smoother surface texture when contrasted with those produced using sulfuric acid alone.
In 2006, oxalic acid was used in semiconductor fabrication for the polishing of silicon wafers.
Answer: False
Explanation: In 2006, oxalic acid found application in the electrochemical-mechanical planarization (CMP) of copper layers within semiconductor device fabrication processes, not silicon wafer polishing.
The reduction of carbon dioxide directly to oxalic acid is being studied as a potential method for carbon capture and utilization.
Answer: True
Explanation: The direct reduction of carbon dioxide to oxalic acid, potentially via electrocatalytic routes, is under investigation as a viable chemical intermediate for carbon capture and utilization initiatives.
Oxalic acid is used in some tooth whitening products.
Answer: True
Explanation: Oxalic acid is incorporated as an ingredient in specific formulations for tooth whitening.
For which application is oxalic acid noted due to its capacity to form a water-soluble complex with ferric iron?
Answer: Rust removal as a cleaning agent
Explanation: Oxalic acid is effectively employed for rust removal, leveraging its capacity to form a water-soluble complex with ferric iron.
How does oxalic acid facilitate the leaching of manganese from ores?
Answer: By acting as a reducing agent, converting MnO₂ to a soluble form.
Explanation: Oxalic acid functions as a reducing agent in the context of manganese ore processing, transforming manganese dioxide into a more soluble species, facilitating leaching with sulfuric acid.
Why is oxalic acid useful in the purification of lanthanides?
Answer: It precipitates lanthanide oxalates that are easily filtered and pure.
Explanation: In lanthanide chemistry, oxalic acid is significant due to its propensity to form hydrated lanthanide oxalates in highly acidic media. These precipitates are crystalline, facilitating facile filtration and yielding products with minimal contamination.
What percentage of oxalic acid produced globally is used as a mordant in dyeing processes?
Answer: Approximately 25%
Explanation: An estimated 25% of the global production volume of oxalic acid is allocated to its application as a mordant in textile dyeing processes.
When oxalic acid is used in aluminum anodizing, how do the resulting coatings compare to those made with sulfuric acid?
Answer: Oxalic acid coatings are thinner and smoother.
Explanation: In aluminum anodizing applications, oxalic acid yields coatings that are characterized by reduced thickness and smoother surface texture when contrasted with those produced via sulfuric acid anodizing.
One pathway for oxalate biosynthesis involves the dehydrogenation of glycolic acid.
Answer: True
Explanation: The dehydrogenation of glycolic acid is identified as one of the principal enzymatic pathways for oxalate biosynthesis.
The spinach family (Amaranthaceae) and the cabbage family (Brassicaceae) are known for containing low levels of oxalates.
Answer: False
Explanation: The spinach family (Amaranthaceae) and the brassica family (e.g., cabbage) are recognized for containing high levels of oxalates, not low levels.
Rhubarb leaves contain a significantly high concentration of oxalic acid, around 10%.
Answer: False
Explanation: Rhubarb leaves are reported to contain approximately 0.5% oxalic acid, not 10%.
Oxalate patinas on limestone monuments are proposed to form from the reaction of the stone with oxalic acid produced by microorganisms.
Answer: True
Explanation: The formation of oxalate patinas on ancient limestone and marble monuments is hypothesized to result from the reaction between the carbonate substrate and oxalic acid produced by associated microorganisms.
Oxalic acid secreted by soil fungi decreases the solubility of metal cations in the soil.
Answer: False
Explanation: Oxalic acid secreted by soil fungi increases the solubility of metal cations, potentially enhancing nutrient availability.
The fungus *Penicillium notatum* has been studied for the industrial production of oxalic acid.
Answer: False
Explanation: The fungus *Aspergillus niger* has been extensively studied for its potential in the industrial production of oxalic acid, not *Penicillium notatum*.
*Oxalobacter formigenes* is a bacterium that helps degrade oxalate in the digestive system of animals.
Answer: True
Explanation: *Oxalobacter formigenes* is a notable gut bacterium implicated in the degradation of oxalate within mammalian digestive systems, including that of humans.
Lactate dehydrogenase (LDH) is primarily involved in aerobic respiration, converting lactic acid back to pyruvate.
Answer: False
Explanation: Lactate dehydrogenase (LDH) catalyzes the conversion of pyruvate to lactic acid, a process crucial for anaerobic glycolysis, not primarily involved in aerobic respiration.
Inhibiting lactate dehydrogenase (LDH) is being explored as a cancer treatment strategy due to cancer cells' reliance on anaerobic metabolism.
Answer: True
Explanation: Given the frequent reliance of neoplastic cells on anaerobic metabolism (the Warburg effect), the inhibition of LDH is being investigated as a therapeutic strategy for cancer.
High amounts of oxalic acid can enhance a plant's resistance to fungal infections by causing cell death.
Answer: False
Explanation: While small amounts of oxalic acid can enhance plant resistance, high concentrations can induce programmed cell death in the plant, thereby facilitating fungal infection.
Parsley has a high oxalic acid content, reported at 1.70%.
Answer: True
Explanation: Parsley is identified in the data as containing a high concentration of oxalic acid, reported at 1.70%.
The lethal oral dose for oxalic acid is estimated to be between 150 and 300 grams.
Answer: False
Explanation: The reported range for the lethal oral dose of oxalic acid is significantly lower, between 15 and 30 grams.
Ingestion of oxalic acid can cause kidney failure because it forms insoluble calcium oxalate crystals that block kidney tubules.
Answer: True
Explanation: Ingestion of oxalic acid can precipitate the formation of solid calcium oxalate within the renal tubules, leading to obstruction and subsequent kidney failure.
Oxalate is known to enhance mitochondrial function by increasing ATP production.
Answer: False
Explanation: Oxalate is recognized for inducing mitochondrial dysfunction, thereby disrupting normal cellular operations within mitochondria, rather than enhancing function.
Approximately 76% of kidney stones are composed of calcium oxalate.
Answer: True
Explanation: The majority of human kidney stones, approximately 76%, are composed of calcium oxalate.
*Oxalis acetosella* is listed as a related compound in the 'See also' section.
Answer: True
Explanation: The 'See also' section lists *Oxalis acetosella* and Potassium hydrogen oxalate as related compounds.
The lowest published lethal oral dose (LD_Lo) for oxalic acid is 600 mg/kg.
Answer: True
Explanation: The lowest published lethal oral dose (LD_Lo) for oxalic acid is documented as 600 mg/kg.
Ethylene glycol ingestion can lead to kidney failure primarily because it is metabolized into oxalic acid, forming calcium oxalate crystals.
Answer: True
Explanation: Upon ingestion, ethylene glycol undergoes metabolic conversion to oxalic acid, a process that can precipitate acute kidney failure via the formation of calcium oxalate crystals.
Oxalic acid plays a dual role in plant-fungi interactions, where high concentrations enhance plant resistance.
Answer: False
Explanation: Oxalic acid exhibits a dual role in plant-fungal interactions: low concentrations may bolster plant defense mechanisms against fungal pathogens, whereas elevated concentrations can induce programmed cell death in plant tissues, thereby promoting fungal ingress.
Which of the following is NOT identified as a pathway for oxalate biosynthesis within the provided source material?
Answer: Oxidation of tartaric acid
Explanation: The provided source material identifies the hydrolysis of oxaloacetate and the dehydrogenation of glycolic acid as pathways for oxalate biosynthesis. Oxidation of tartaric acid is not mentioned.
Which plant families are noted for being high in oxalates?
Answer: Spinach family (Amaranthaceae) and Brassica family
Explanation: The Amaranthaceae (spinach family) and the Brassicaceae (e.g., cabbage, broccoli) are botanical families recognized for their significant oxalate content.
What is the approximate concentration of oxalic acid found in rhubarb leaves, as indicated by the source?
Answer: 0.5%
Explanation: Rhubarb leaves are reported to contain approximately 0.5% oxalic acid.
What is the proposed mechanism for the formation of oxalate patinas on ancient limestone and marble monuments?
Answer: Reaction between the carbonate stone and oxalic acid from microorganisms.
Explanation: The formation of oxalate patinas observed on ancient limestone and marble monuments is hypothesized to result from the reaction between the carbonate substrate and oxalic acid produced by associated microorganisms.
How does oxalic acid secreted by soil fungi affect soil nutrients?
Answer: It increases the solubility of metal cations, making them more available.
Explanation: The secretion of oxalic acid by soil fungi has the effect of increasing the solubility of metal cations, thereby potentially enhancing the availability of certain soil nutrients.
Which bacterium found in the gut plays a role in degrading oxalate?
Answer: *Oxalobacter formigenes*
Explanation: *Oxalobacter formigenes* is a notable gut bacterium implicated in the degradation of oxalate within mammalian digestive systems.
What is the function of lactate dehydrogenase (LDH) in anaerobic metabolism, as described in the source?
Answer: To catalyze the conversion of pyruvate to lactic acid, regenerating NAD+.
Explanation: Lactate dehydrogenase (LDH) catalyzes the reversible conversion of pyruvate to lactic acid. This reaction is critical for regenerating NAD+ from NADH, a necessary cofactor for the continuation of glycolysis under anaerobic conditions.
Why is inhibiting LDH considered a potential cancer treatment strategy?
Answer: Because cancer cells often rely heavily on anaerobic metabolism (Warburg effect).
Explanation: Given the frequent reliance of neoplastic cells on anaerobic metabolism (the Warburg effect), the inhibition of LDH is being investigated as a therapeutic strategy for cancer.
What is the role of oxalic acid in the interaction between pathogenic fungi and plants?
Answer: Small amounts enhance resistance, but high amounts facilitate infection by causing cell death.
Explanation: Oxalic acid exhibits a dual role in plant-fungal interactions: low concentrations may bolster plant defense mechanisms against fungal pathogens, whereas elevated concentrations can induce programmed cell death in plant tissues, thereby promoting fungal ingress.
What is the reported range for the lethal oral dose of oxalic acid?
Answer: 15 to 30 grams
Explanation: The reported range for the lethal oral dose of oxalic acid is between 15 and 30 grams.
The precipitation of which compound within the renal tubules is identified as the primary cause of kidney failure following oxalic acid ingestion?
Answer: Calcium oxalate
Explanation: Ingestion of oxalic acid can precipitate the formation of solid calcium oxalate within the renal tubules, leading to obstruction and subsequent kidney failure.
What effect does oxalate have on mitochondria, according to the source?
Answer: It causes mitochondrial dysfunction.
Explanation: Oxalate is recognized for inducing mitochondrial dysfunction, thereby disrupting normal cellular operations within mitochondria.
What percentage of kidney stones are composed of calcium oxalate?
Answer: Approximately 76%
Explanation: The majority of human kidney stones, approximately 76%, are composed of calcium oxalate.
How does the ingestion of ethylene glycol lead to potential kidney failure?
Answer: It is metabolized into oxalic acid, forming calcium oxalate crystals in the kidneys.
Explanation: Upon ingestion, ethylene glycol undergoes metabolic conversion to oxalic acid, a process that can precipitate acute kidney failure via the formation of calcium oxalate crystals.