Pharmaceutical Organic Chemistry I PC101 Quiz
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Questions and Answers

What is the molecular formula for pentane?

  • C5H10
  • C5H18
  • C5H12 (correct)
  • C5H14

Which of the following is the correct IUPAC name for C8H18?

  • Heptane
  • Octane (correct)
  • Nonane
  • Butane

What prefix is used to indicate three substituents in an alkane's name?

  • penta-
  • tetra-
  • di-
  • tri- (correct)

In naming alkanes, which of the following groups are not considered in alphabetical order?

<p>di- and tri- (C)</p> Signup and view all the answers

Which alkane has the molecular formula C11H24?

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

When naming alkanes, how should the carbon chain be numbered?

<p>From the end that gives the lowest number to the substituents (D)</p> Signup and view all the answers

For a chain with two identical substituents, which prefix is used to denote their quantity?

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

Which of the following is NOT a saturated hydrocarbon?

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

What is the primary mechanism of halogenation of alkanes?

<p>Free radical mechanism (C)</p> Signup and view all the answers

Which halogen is more reactive and non-selective in the halogenation of alkanes?

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

When performing a Clemmensen reduction, what reagents are typically used?

<p>Zn/Hg/HCl (D)</p> Signup and view all the answers

What is the result of decarboxylation of carboxylic acids?

<p>Reduction in carbon content (B)</p> Signup and view all the answers

In a halogenation reaction, which hydrogen is most likely to react with bromine?

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

What is the bond angle characteristic of sp3 hybridized carbon atoms in alkanes?

<p>109.5º (A)</p> Signup and view all the answers

What is the outcome of reducing carbonyl compounds?

<p>Same number of carbon atoms as starting material (A)</p> Signup and view all the answers

Which reagent is used in the Wolf-Kishner reduction?

<p>NH2–NH2/base (D)</p> Signup and view all the answers

What is the common name for the compound CH3–CH2–CH2–CH3?

<p>n-pentane (B)</p> Signup and view all the answers

Which of the following represents an isoalkane?

<p>CH3–CH(CH3)–CH2–CH3 (A)</p> Signup and view all the answers

Which compound can be classified as neopentane?

<p>CH3–C(CH3)2–CH3 (A)</p> Signup and view all the answers

What is the result of removing one hydrogen atom from an alkane?

<p>Forming an alkyl group (B)</p> Signup and view all the answers

Which reaction is commonly used to prepare alkanes from alkyl halides?

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

What is the significance of using catalysts like Ni or Pd in catalytic reduction?

<p>To enhance the reaction speed (C)</p> Signup and view all the answers

Which name corresponds to a compound with the structure CH3–CH(CH3)–CH2–C(CH3)2–CH2?

<p>6,6-Diethyl-4-isopropyl-2,3-dimethyloctane (B)</p> Signup and view all the answers

Which of the following correctly describes the structure of isopentane?

<p>CH3–CH(CH3)–CH2–CH3 (C)</p> Signup and view all the answers

What is the bond angle associated with a structure mentioned in the content?

<p>108° (C)</p> Signup and view all the answers

Which of the following statements correctly describes the behavior of five and six membered rings?

<p>They do not undergo ring opening and perform normal substitution reactions. (C)</p> Signup and view all the answers

In a hydrogenation reaction at 200°C with H2/Ni, what product is formed from propene?

<p>C3H8 (D)</p> Signup and view all the answers

What is the product when cyclohexene reacts with chlorine in the presence of UV light?

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

What type of reaction occurs when cyclohexene is treated with NaOH?

<p>Normal substitution reactions (D)</p> Signup and view all the answers

What is the primary outcome of the nitration process described?

<p>Replacement of hydrogen with a NO2 group (B)</p> Signup and view all the answers

Which reaction mechanism is involved in the nitration process?

<p>Free radical mechanism (C)</p> Signup and view all the answers

During sulphonation, to which type of hydrogen atom does sulphonation primarily occur?

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

What is produced during the oxidation of alkanes when burned with oxygen?

<p>Carbon dioxide and water (D)</p> Signup and view all the answers

What condition is necessary for the pyrolysis of alkanes to occur?

<p>Absence of oxygen (B)</p> Signup and view all the answers

What type of acid is used in the sulphonation process?

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

What is one of the main products formed from the thermal decomposition (cracking) of alkanes?

<p>Smaller alkanes and alkenes (A)</p> Signup and view all the answers

Which reaction requires a temperature of around 500ºC and concentrated nitric acid to replace a hydrogen with an NO2 group?

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

What is the general formula for alicyclic compounds (cycloalkanes)?

<p>C_nH_2n (A)</p> Signup and view all the answers

In naming '1-Ethyl-3-methylcyclohexane', how should you assign the substituent numbers?

<p>Give the substituents the lowest possible numbers (B)</p> Signup and view all the answers

What happens if the side chain has more carbon atoms than the ring in a cycloalkane?

<p>The ring is treated as a substituent (A)</p> Signup and view all the answers

Which of the following is true about trivial names of cycloalkanes?

<p>They are named as polymethylene derivatives (C)</p> Signup and view all the answers

What is a prerequisite for using internal Wurtz reaction in preparing cycloalkanes?

<p>Halogen atoms separated by less than six carbon atoms (D)</p> Signup and view all the answers

When preparing alicyclic compounds, what is a common reagent used in the dehalogenation process?

<p>Zn or Na (D)</p> Signup and view all the answers

What should be removed from the name of a cycloalkane to convert it to a radical?

<p>The suffix '–ane' (B)</p> Signup and view all the answers

Which of the following correctly represents a cycloalkane name?

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

Flashcards

Saturated Hydrocarbons (Alkanes)

Hydrocarbons containing only single bonds between carbon atoms.

General Formula of Alkanes

CnH2n+2, where 'n' is the number of carbon atoms

IUPAC Nomenclature

A systematic method for naming organic compounds, including alkanes.

Parent Chain

The longest continuous chain of carbon atoms in a molecule.

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Alkyl Substituents

Atoms or groups of atoms that branch off the parent chain.

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Naming Alkanes with Substituents

Number the parent chain to give the substituents the lowest possible numbers.

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Naming with Multiple Substituents

Order substituent names alphabetically, numbers separated by commas and numbers and letters separated by dashes.

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Methane

An alkane with one carbon atom and four hydrogen atoms.

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Ethane

An alkane with two carbon atoms and six hydrogen atoms.

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Propane

An alkane with three carbon atoms and eight hydrogen atoms.

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Butane

An alkane with four carbon atoms and ten hydrogen atoms.

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Naming with prefixes

di-, tri-, tetra-, etc used to show multiples of the same group attached.

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Alkanes

Saturated hydrocarbons containing only single bonds between carbon atoms.

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Normal Alkanes

Straight-chain alkanes with no branching.

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Isoalkanes

Branched alkanes with two methyl groups at one end of the side chain.

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Neoalkanes

Branched alkanes with three methyl groups at one end of the chain.

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Alkyl Groups

Groups of atoms that are part of a larger molecule, formed by removing one hydrogen atom from an alkane and replacing suffix '-ane' with '-yl'.

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n-Prefix

Indicates a normal alkane with a straight carbon chain.

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Iso-Prefix

Indicates a branched alkane with two methyl groups at the end.

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Neo-Prefix

Indicates a branched alkane with three methyl groups at the end.

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Catalytic Reduction

Converting unsaturated hydrocarbons (alkenes/alkynes) to alkanes using a catalyst (e.g., nickel, palladium).

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Alkyl Halides

Organic compounds in which a halogen is bonded to a saturated carbon chain

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Wurtz Reaction

A reaction that combines two alkyl halides in the presence of sodium to create a longer alkane.

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Halogenation of Alkanes

A substitution reaction where a halogen atom replaces a hydrogen atom in an alkane.

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Alkane Structure

Alkanes have sp3 hybridized carbon atoms with bond angles of 109.5°. They are non-polar and unreactive.

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Free Radical Mechanism

A chain reaction mechanism involving free radicals in halogenation reactions.

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Gringard Reagent

A reagent formed by reacting an alkyl halide with magnesium.

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Reduction of Carbonyl Compounds

Converting Carbonyl compounds to alcohols, aldehyde to alcohol and ketones to alcohols with the same number of carbons.

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Decarboxylation of Carboxylic Acids

A reaction removing a carboxyl group (-COOH) from a carboxylic acid, resulting in loss of one carbon.

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Alkyl Halide

A molecule where a hydrogen in an alkane is replaced by a halogen.

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Halogen Reactivity

Reactivity of halogens in halogenation reactions follows the trend: Fluorine > Chlorine > Bromine > Iodine.

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Selective Halogenation

Bromine is more selective than chlorine, usually reacting with a tertiary hydrogen.

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Halogenation of Alkanes

A reaction where a halogen replaces a hydrogen in an alkane, usually requiring high temperatures or light to initiate.

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Alkane Nitration

A reaction where a hydrogen atom in an alkane is replaced by a nitro group (NO2) using concentrated nitric acid at a high temperature (500°C).

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Alkane Sulphonation

A reaction where a hydrogen atom in an alkane is replaced by a sulphonic acid group (SO3H) using oleum (fuming sulfuric acid).

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Alkane Oxidation

A reaction where alkanes react with oxygen (or air) at high temperatures (500-700°C) to form carbon dioxide, water, and releasing large amounts of heat.

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Alkane Pyrolysis (Cracking)

The thermal decomposition of alkanes into smaller alkanes and alkenes at high temperatures in the absence of oxygen.

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Free Radical Mechanism (Nitration)

A mechanism where free radicals are formed during the nitration of alkanes, leading to various product formations.

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Concentrated nitric acid

A very strong acid used to replace a hydrogen atom with a nitro group in a reaction process.

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Oleum (fuming sulfuric acid)

A more concentrated form of sulfuric acid containing dissolved sulfur trioxide (SO3) that replaces a hydrogen atom with a sulphonate group.

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Alicyclic Compounds (Cycloalkanes)

Alkanes where carbon atoms form a ring structure.

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General Formula of Cycloalkanes

CnH2n

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Cycloalkane Nomenclature

Naming cycloalkanes based on the number of carbons in the ring and substituents (e.g., 1-Ethyl-3-methylcyclohexane).

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Substituent Numbering

Assign the lowest possible numbers for substituent positions.

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Trivial Cycloalkane Names

Naming some cycloalkanes as polymethylene derivatives (e.g., trimethylene).

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Cycloalkane Preparation (Dehalogenation)

Creating cycloalkanes by reacting alpha,omega-dihaloalkanes using zinc or sodium.

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Intermolecular Wurtz Reaction

Cycloalkane formation when dihalides have more than 6 carbons between them.

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Internal Wurtz Reaction

Cycloalkane formation when dihalides have 6 or fewer carbons between them.

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600°C

Temperature used in a reaction but no definition in current context

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Bond angle of 108° in molecules

The angle between atoms in molecules like cyclic structures, close to the tetrahedral angle of 109.5°

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Five/Six membered rings vs. Three/Four

Five and six membered rings don't readily undergo ring-opening reactions, unlike three and four membered rings.

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Hydrogenation reaction types

Hydrogenation using different catalysts and temperatures may result in either the product expected or no reaction occuring at all.

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Electrophilic addition reaction examples

Electrophilic additions demonstrate various reaction pathways and products including the addition of halogens, HI, and adding water to cyclic alkenes.

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Reactions of Five/Six membered rings

Five and six membered rings usually undergo typical substitution reactions, not ring-opening reactions.

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Example of substitution reaction on Five/Six member rings

Example: Cyclohexane reacts with chlorine in the presence of UV light, resulting in a substitution reaction.

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Reaction with Cyclohexanol

Cyclohexanol can be converted to cyclohexene using strong bases like alcoholic KOH

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Study Notes

Course Information

  • Course Title: Pharmaceutical Organic Chemistry I PC101
  • Instructor: Mona S. El-Zoghbi, Ph.D. Pharm. Sc.
  • Department: Pharmaceutical Chemistry Department
  • Email: [email protected]

Intended Learning Outcomes (ILOs)

  • Students will be able to recognize several organic terms.
  • Students will be able to identify different types of chemical bonds.
  • Students will be able to recognize different classes of organic compounds.
  • Students will be able to assess the structural features of organic compounds and their IUPAC names.
  • Students will be able to demonstrate alkanes, alkenes, alkynes, and alkyl halides (nomenclature, physical and chemical properties, preparation, and chemical reactions).
  • Students will be able to classify different reaction mechanisms.
  • Students will be able to outline fundamental principles and applications of stereochemistry, stereo-dynamic, hydroxyl, and carbonyl compounds.
  • Students will be able to identify principles of aromaticity and benzenoid compounds.

Organic Compounds

  • Acyclic: Open chain aliphatic compounds
    • Alicyclic: Carbocyclic
      • Aromatic
    • Cyclic: Carbocyclic
      • Heterocyclic

Organic Compound Types

  • Organic compounds: Compounds containing carbon in C-C bonds. Organic compounds come from organisms.
  • Carbocyclic compounds: Cyclic organic compounds containing only carbon and hydrogen.
  • Alicyclic compounds: Saturated cyclic compounds containing only carbon and hydrogen. They behave like alkanes (examples: cyclopropane, cyclohexane).
  • Aromatic compounds: Carbocyclic compounds containing a benzene ring or cyclic compounds with a low H/C ratio (examples: benzene, naphthalene).
  • Heterocyclic compounds: Cyclic organic compounds containing one or more heteroatoms (nitrogen, sulfur, or oxygen). (examples: pyridine, furan, thiophen).

Aliphatic Hydrocarbons

  • Saturated: Alkanes (general formula CnH2n+2)
  • Unsaturated: Alkenes (contain double bonds), Alkynes (contain triple bonds)

Alkanes

  • General formula: CnH2n+2
  • Nomenclature:
    • Common names ("trivial names")
    • IUPAC system (International Union of Pure and Applied Chemistry)
  • Naming rules include:
    • Longest continuous carbon chain
    • Substituent numbering for lowest numbers
    • Multiple substituents are listed in alphabetical order.

Alkyl groups

  • Obtained by removing one hydrogen from an alkane.
  • Replace the "-ane" suffix with "-yl"
  • Examples: methyl from methane, ethyl from ethane, propyl from propane
  • "iso" and "neo" are prefixes associated with some branched alkyl groups.

Alkane Preparations

  • From unsaturated hydrocarbons (catalytic reduction):
    • Reacting unsaturated hydrocarbons with hydrogen and a catalyst (eg. Ni or Pd).
  • From alkyl halides:
    • Reduction: alkyl halides react with substances such as Zn/HCl, Mg/Hg/EtOH, or LiAlH4 to form alkanes.
    • Wurtz reaction: alkyl halides react with sodium metal to yield alkanes.
  • From Grignard reagents: alkyl halides react with magnesium metal to form alkanes using specific conditions
  • From carbonyl compounds (e.g. Clemmenson, Wolf-Kischner reductions): reducing carbonyl compounds for alkanes using different catalysts.

Alkane Reactions

  • Generally inert: Do not readily react.
  • Halogenation: Substitution reactions at high temperatures or with light. Chlorine reacts more readily, but is less selective. Iodine is less reactive and more selective.

Cycloalkanes

  • Alkanes with cyclic carbon structures.
  • General formula: CnH2n
  • Nomenclature:
    • Prefix "cyclo-" is added to the alkane name to indicate the cyclic structure.
    • Following standard alkane naming rules.

Cycloalkane Preparations

  • From other cyclic compounds: Certain cyclic compounds react to form cycloalkane.
  • By dehalogenation of dihalogen derivatives: Dihalogen derivatives react with reagents to yield cycloalkanes.

Reactions of Cycloalkanes and Five/Six-membered Rings

  • Baeyer Strain theory: The difference between bond angle from tetrahedral angle will affect their stability and strain of the ring structure
  • Cycloalkanes with smaller ring sizes have higher strain.
  • Strained five/six membered rings may still undergo normal substitution reactions.

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Description

This quiz tests your knowledge on fundamental concepts in Pharmaceutical Organic Chemistry I. You will be assessed on your understanding of organic terms, types of chemical bonds, and various classes of organic compounds. Prepare to classify reaction mechanisms and outline key principles of stereochemistry.

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