Organic Chemistry: Stereoisomers

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Questions and Answers

In the first stage of glycolysis, which compound directly utilizes ATP?

  • Dihydroxyacetone phosphate
  • Glucose
  • Glucose-6-phosphate (correct)
  • Fructose-6-phosphate

Which molecule is produced after phosphorylation of glucose in glycolysis?

  • Fructose-1,6-bisphosphate
  • ATP
  • ADP
  • Glucose-6-phosphate (correct)

What is the role of ATP in the process described?

  • It serves as a substrate for forming glucose-6-phosphate.
  • It transfers a phosphate group to glucose. (correct)
  • It generates dihydroxyacetone phosphate.
  • It is converted to glucose.

Which of the following is a key intermediate compound in glycolysis as shown above?

<p>Glucose-6-phosphate (A)</p> Signup and view all the answers

What is the structural formula for dihydroxyacetone phosphate as depicted?

<p>A three-carbon molecule with a phosphate group (A)</p> Signup and view all the answers

What is the chemical structure represented by the term β-D-glucosamine?

<p>A modified glucose molecule with an amino group (D)</p> Signup and view all the answers

Which molecule is characterized as fructose-1,6-bisphosphate?

<p>A six-carbon molecule with two phosphate groups (C)</p> Signup and view all the answers

What is the molecular characteristic of dihydroxyacetone phosphate?

<p>A three-carbon sugar phosphate (D)</p> Signup and view all the answers

Which of the following correctly describes glyceraldehyde-3-phosphate?

<p>An important intermediate in cellular respiration and glycolysis (C)</p> Signup and view all the answers

Which molecule contains a phosphate group crucial for energy transfer?

<p>Fructose-6-phosphate (C)</p> Signup and view all the answers

What distinguishes β-D-galactosamine from β-D-glucosamine?

<p>The modification of a hydroxyl group into an amino group (D)</p> Signup and view all the answers

What is the role of ATP in the context of the provided structures?

<p>It acts as an energy carrier in biochemical reactions. (B)</p> Signup and view all the answers

Which statement is accurate regarding fructose-6-phosphate and fructose-1,6-bisphosphate?

<p>Fructose-6-phosphate has one phosphate group, while fructose-1,6-bisphosphate has two. (A)</p> Signup and view all the answers

What is the chemical structure of dimethyl sulfide?

<p>CH3-S-CH3 (C)</p> Signup and view all the answers

Which compound is an example of an ether?

<p>methyl propyl ether (B)</p> Signup and view all the answers

What is the general structure of a sulfonic acid?

<p>R-SO2OH (B)</p> Signup and view all the answers

Which structure represents a tertiary alcohol?

<p>R2CH(OH)R (A)</p> Signup and view all the answers

What is formed when methanethiol undergoes mild oxidation?

<p>disulfide (D)</p> Signup and view all the answers

Which isomer of propyl alcohol has the hydroxyl group at the end of the carbon chain?

<p>1-propanol (C)</p> Signup and view all the answers

Which of the following compounds is known as tetrahydrofuran?

<p>C4H8O (A)</p> Signup and view all the answers

What is the structural name for para-cresol?

<p>4-hydroxytoluene (A)</p> Signup and view all the answers

What is the primary feature of sulfinic acids?

<p>They contain a sulfur atom bonded to a carbon chain and a hydroxyl group. (B)</p> Signup and view all the answers

Which of the following is NOT a isomer of dihydroxybenzene?

<p>dihydroxybenzene acid (A)</p> Signup and view all the answers

What is produced as a result of the decarboxylation of β-keto acids?

<p>Ketone (A)</p> Signup and view all the answers

What distinguishes diethyl ether from other ethers?

<p>It has two ethyl groups connected by an oxygen. (A)</p> Signup and view all the answers

Which molecule is formed from the β-oxidation of fatty acids?

<p>β-keto acid (C)</p> Signup and view all the answers

What is the functional group present in phenol?

<p>Alcohol (C)</p> Signup and view all the answers

Which of the following statements about ethanethiol is correct?

<p>It is an alkane with a thiol group. (A)</p> Signup and view all the answers

Which statement is true regarding secondary alcohols?

<p>They have the hydroxyl group on a carbon bonded to two carbon atoms. (B)</p> Signup and view all the answers

Which compound is closely associated with the formation of fumarate from succinate?

<p>Succinate (D)</p> Signup and view all the answers

Which is the correct relationship among different isomers of cresol?

<p>They differ only in the position of the hydroxyl group on the benzene ring. (D)</p> Signup and view all the answers

What is the final product after the decarboxylation of a β-keto acid?

<p>Ketone (A)</p> Signup and view all the answers

What distinguishes enols from other alcohols?

<p>They possess a carbon-carbon double bond adjacent to the hydroxyl group. (B)</p> Signup and view all the answers

Which of the following compounds is categorized as a monokarbonsavak?

<p>Benzoic acid (B)</p> Signup and view all the answers

What type of acid is a β-hydroxy acid before its conversion into a β-keto acid?

<p>Monohydroxy acid (B)</p> Signup and view all the answers

Which process involves the conversion of a β-hydroxy acid to a β-keto acid?

<p>Oxidation (D)</p> Signup and view all the answers

Which feature is characteristic of β-keto acids?

<p>They have a hydroxyl group adjacent to the carbonyl group. (A)</p> Signup and view all the answers

What is an alkyl sulfate?

<p>A compound characterized by the presence of a sulfate group (D)</p> Signup and view all the answers

Which describes an alkylbenzene sulfonate?

<p>It contains an alkyl chain and a sulfonate group. (D)</p> Signup and view all the answers

What constitutes an invert soap?

<p>A type of quaternary ammonium salt (D)</p> Signup and view all the answers

What is produced during the dehydration of a β-hydroxy acid?

<p>An α,β-unsaturated compound (D)</p> Signup and view all the answers

What functional group is common in both alkyl sulfates and alkylbenzene sulfonates?

<p>Sulfate group (D)</p> Signup and view all the answers

Which structure is associated with quaternary ammonium salts?

<p>A positively charged nitrogen atom connected to four organic groups. (C)</p> Signup and view all the answers

How is a β-hydroxy acid characterized?

<p>By having one hydroxyl group adjacent to a carboxyl group (A)</p> Signup and view all the answers

Which of the following compounds would not be classified as a soap?

<p>Alkylbenzene sulfonate (B)</p> Signup and view all the answers

Flashcards

Primary alcohol structure

A primary alcohol has a hydroxyl group (-OH) attached to a carbon atom bonded to only one other carbon atom.

Secondary alcohol structure

A secondary alcohol has a hydroxyl group (-OH) attached to a carbon atom bonded to two other carbon atoms.

Tertiary alcohol structure

A tertiary alcohol has a hydroxyl group (-OH) attached to a carbon atom bonded to three other carbon atoms.

Isomers of propyl alcohol

1-propanol and 2-propanol are isomers because they have the same molecular formula (C3H8O) but different structural arrangements.

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Phenol structure

A phenol is an aromatic compound containing a hydroxyl group (-OH) directly bonded to an aromatic ring.

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Cresol isomers

Cresol is a methylphenol. ortho-, meta-, and para-cresol are isomers of cresol differing in the positions of the methyl and hydroxyl groups on the benzene ring.

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Dihydroxybenzene isomers

Dihydroxybenzene isomers have two hydroxyl groups on a benzene ring, varying in their relative positions (ortho, meta, para).

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Benzyl alcohol structure

Benzyl alcohol is an alcohol with a hydroxyl group (-OH) attached to a benzyl group (a benzene ring that has an attached methyl group).

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Nitroglycerin chemical formula

C3H5N3O9

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Diethyl ether

An ether with two ethyl groups attached to the oxygen atom.

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Dimethyl sulfide

A molecule with two methyl groups bonded to a sulfur atom.

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Sulfonic acid general structure

R-S(=O)2-OH

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Sulfinic acid general structure

R-S(=O)-OH

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Sulfone general structure

R-S(=O)2-R'

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Oxidation of methanethiol

The process of converting methanethiol to a disulfide through gaining oxygen.

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2-Mercaptoethanol

An alcohol with a sulfhydryl group at the 2-position.

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Alkyl Sulfate

A type of anionic surfactant with a sulfate group (SO4-) attached to a long hydrocarbon chain.

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Alkylbenzene Sulfonate

An anionic surfactant with a sulfonate group (SO3-) attached to a benzene ring connected to a long hydrocarbon chain.

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Invert Soap

A type of cationic surfactant with a positively charged quaternary ammonium group attached to a long hydrocarbon chain.

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Dehydration of a β-hydroxy acid

A chemical reaction where water is removed from a β-hydroxy acid, resulting in the formation of an α,β-unsaturated carboxylic acid.

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β-hydroxy acid

A carboxylic acid with a hydroxyl group (-OH) attached to the carbon atom adjacent to the carboxyl group.

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α,β-unsaturated carboxylic acid

A carboxylic acid with a double bond between the alpha and beta carbon atoms.

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Beta-oxidation of monocarboxylic acids

A metabolic pathway that breaks down fatty acids into acetyl-CoA.

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Beta-hydroxy acid

An intermediate molecule in the oxidation of fatty acids

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Beta-keto acid

A key intermediate in fatty acid oxidation

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Decarboxylation

A reaction that removes a carboxyl group (COOH) releasing CO2

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Fumarate formation from succinate

A metabolic step converting succinate to fumarate.

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Ketone formation

A molecule with a ketone group is created during oxidation.

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Monocarboxylic acids

Organic compounds containing a single carboxyl group.

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Benzoic acid

A simple aromatic carboxylic acid, common in nature and used for various preparations

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What is glucose-6-phosphate?

Glucose-6-phosphate is a molecule formed in the first step of glycolysis when glucose reacts with ATP. It's a crucial intermediate in energy metabolism.

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What is dihydroxyacetone phosphate?

Dihydroxyacetone phosphate (DHAP) is a three-carbon sugar formed during glycolysis after glucose-6-phosphate is converted. It's an isomer of glyceraldehyde-3-phosphate.

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What is ATP?

ATP (adenosine triphosphate) is a molecule that provides energy for cellular processes. It's involved in the phosphorylation of glucose to glucose-6-phosphate in the first step of glycolysis.

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What is ADP?

ADP (adenosine diphosphate) is a molecule produced when ATP loses a phosphate group. It's a product of the phosphorylation reaction in the first step of glycolysis.

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What is glycolysis?

Glycolysis is the first stage of cellular respiration where glucose is broken down into pyruvate. This process takes place in the cytoplasm and produces ATP.

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Glucose

A simple sugar with the molecular formula C6H12O6, found in many plants and animals as a source of energy.

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Fructose

A simple sugar with the molecular formula C6H12O6, commonly found in fruits and honey, known for its sweetness.

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Galactose

A simple sugar with the molecular formula C6H12O6, found in milk and dairy products, used in the synthesis of lactose.

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What is the difference between glucose and fructose?

Glucose and fructose have the same molecular formula (C6H12O6) but different structures. Glucose is an aldose (a sugar with an aldehyde group) while fructose is a ketose (a sugar with a ketone group).

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What is a phosphate group?

A phosphate group is a chemical group consisting of a phosphorus atom bonded to four oxygen atoms (PO4).

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What is fructose-1,6-bisphosphate?

Fructose-1,6-bisphosphate is a sugar phosphate with two phosphate groups, crucial in glycolysis, the process of glucose breakdown.

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Study Notes

Stereoisomers

  • Various molecules exist as stereoisomers, differing in how groups are arranged in 3-dimensional space.
  • Examples are D-glyceraldehyde and L-glyceraldehyde, which differ in the spatial arrangement of the hydroxyl (-OH) and aldehyde groups.

Organic Chemistry

  • Structural Formulas: Charts show graphical representations of molecules, highlighting arrangement of atoms.
  • Functional Groups: Many organic compounds contain specific functional groups (e.g., hydroxyl -OH, carboxyl -COOH, amino -NH2, and various others), each with characteristic properties.
  • Systematic Names: Used to precisely define organic compounds (e.g., methane, ethane, propane).
  • Isomers: Same molecular formula but different structures.
  • Stereoisomers: Same atoms, same bonds but different 3D arrangement.
  • Configuration: Spatial arrangement of groups around a chiral center.
  • Nomenclature: Rules for naming organic molecules using prefixes and suffixes.
  • Reactions: Processes that involve the conversion of reactants into products by changes in chemical bonds; illustrated in different sections of the document
  • Structure and Bonding: Diagrams indicate the arrangements and types of bonds between atoms in different molecules.
  • Conformations: Different spatial arrangements of a molecule due to the rotation around single bonds
  • Functional groups: Key groups within molecules that give them specific properties (e.g., aldehydes, ketones, alcohols)
  • Isomerism: Compounds with the same molecular formula but different structures (e.g., cis-trans isomers)

Aromatic Compounds

  • Polycyclic Aromatic Hydrocarbons (PAHs): Benzene, naphthalene, anthracene, and phenanthrene are examples of planar cyclic compounds with delocalized pi electrons— important in many chemical and biological systems.
  • Toluene: A substituted benzene with a methyl group, acting as a building block in some chemical syntheses.
  • Xylenes (ortho-, meta-, para-): Methyl-substituted benzenes.

Heterocyclic Compounds

  • Nitrogen-containing Rings: Examples like pyrrole, imidazole, pyridine, pyrimidine, purine, indole, thiophene, and other cyclic structures with nitrogen atoms— crucial in various biochemical processes.

Other Organic Compounds

  • Alcohols and Phenols: Contain hydroxyl groups (-OH), important for hydrogen bonding and intermolecular interactions.
  • Aldehydes and Ketones: Contain carbonyl groups (C=O), central functional groups, often involved in chemical reactions.
  • Amines: Nitrogen-containing organic compounds with wide applications in many areas, like drugs and polymers
  • Ethers: Contain an oxygen atom bridging two hydrocarbon groups; used in various organic syntheses and as solvents.
  • Lipids: Include diverse structures from fatty acids to triglycerides, crucial for biological membranes and energy storage.
  • Carbohydrates: Include monosaccharides such as glucose, fructose, and galactose; important for energy storage, structural support (e.g., cellulose), and cell recognition. Structural formulas show the connections between carbon atoms and their related functional groups (e.g., hydroxyl and carbonyl).
  • Carboxylic Acids: Contain carboxyl groups (-COOH). Used in various chemical synthesis and biological systems; Examples include formic, acetic, and oxalic acids.

Chemical Reactions

  • Addition Reactions: adding atoms or groups to molecules (e.g., addition of bromine or hydrogen chloride to alkenes).
  • Substitution Reactions: replacing an atom or group in a molecule (e.g., chlorination of methane).
  • Oxidation-Reduction: processes in which electrons are transferred between molecules (e.g., oxidation of alcohols to aldehydes or ketones).
  • Saponification: Reaction between a fat or oil and a strong base, creating soap
  • Esterification: Reaction between a carboxylic acid and an alcohol, producing an ester.
  • Acylation: Replacement of a hydrogen atom, or functional group with an acyl group
  • Reduction: gain of electrons; decrease in oxidation number
  • Oxidation: loss of electrons; increase in oxidation number

Other Topics

  • Stereochemistry/Stereoisomers: Explanations of isomers with the same atomic structure but differing spatial arrangements
  • Structure-Function Relationships: Correlations between the structure of a molecule and its properties or biological function.
  • Synthesis: Processes that create new chemical compounds by transforming existing ones.

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