Pharmaceutical Organic Chemistry I PC101 Quiz

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Questions and Answers

The rule that states electrons fill subshells of the lowest available energy is known as the ______ Rule.

Aufbau

A ______ pair refers to a pair of valence electrons that are not shared with another atom.

lone

Carbon typically forms ______ covalent bonds.

4

Different classes of organic compounds can be demonstrated, such as ______, alkenes, and alkynes.

<p>alkanes</p> Signup and view all the answers

The principles of ______ are essential for understanding the spatial arrangement of atoms in a molecule.

<p>stereochemistry</p> Signup and view all the answers

Compounds constructed of strong covalent bonds are more stable than compounds incorporating one or more relatively weak ______.

<p>bonds</p> Signup and view all the answers

The distribution of electrons at sites of reaction is affected by electronic ______.

<p>effects</p> Signup and view all the answers

When atoms are crowded together, van der Waals repulsions produce an unfavorable steric ______.

<p>hindrance</p> Signup and view all the answers

The solvent selected for a given reaction may exert a strong ______ on its course.

<p>influence</p> Signup and view all the answers

A full head arrow indicates complete movement or shift of an ______ pair.

<p>electron</p> Signup and view all the answers

Molecules with ______ pairs of electrons can have various shapes such as tetrahedral, trigonal, and linear.

<p>lone</p> Signup and view all the answers

The bond angles in a tetrahedral configuration are approximately ______ degrees.

<p>109.5</p> Signup and view all the answers

Isomers are different compounds that have the same ______ formula.

<p>molecular</p> Signup and view all the answers

Resonance involves the delocalization of ______ electrons within certain molecules.

<p>pi</p> Signup and view all the answers

A primary carbon is one that is bonded to no more than ______ other carbon atom.

<p>one</p> Signup and view all the answers

The hydrogen bond is weaker than an ordinary covalent bond but stronger than ______ interactions.

<p>dipole–dipole</p> Signup and view all the answers

Dipole–dipole forces are attractive forces between the positive end of one ______ molecule and the negative end of another.

<p>polar</p> Signup and view all the answers

Ethyl alcohol has a higher boiling point than dimethyl ether due to the presence of strong ______ bonds.

<p>hydrogen</p> Signup and view all the answers

In dimethyl ether, the intermolecular forces are weaker dipole–dipole interactions and do not include ______.

<p>hydrogen bonds</p> Signup and view all the answers

Many organic compounds, especially ______ and other hydrocarbons, are nearly insoluble in water.

<p>alkanes</p> Signup and view all the answers

Organic compounds that are water soluble, such as ethanol and ______, generally have hydrogen bond acceptor and donor groups.

<p>acetone</p> Signup and view all the answers

A chemical ______ is the transformation of the reactants into the reaction products.

<p>reaction</p> Signup and view all the answers

In a reaction, the ______ refers to the organic compound undergoing change.

<p>reactant</p> Signup and view all the answers

The final result of a chemical reaction is referred to as the ______.

<p>product</p> Signup and view all the answers

In an addition reaction, the number of ______ in the substrate molecule increases.

<p>σ-bonds</p> Signup and view all the answers

If the number of hydrogen atoms bonded to a carbon ______, that carbon has been oxidized.

<p>decreases</p> Signup and view all the answers

Arrowheads must direct towards an electron deficient species which may be a positive charge or the positive end of a polarized ______

<p>bond</p> Signup and view all the answers

The products of bond breaking are not stable and cannot be isolated for prolonged ______

<p>study</p> Signup and view all the answers

An electron deficient atom or molecule that has an affinity for an electron pair is known as an ______

<p>electrophile</p> Signup and view all the answers

An atom or molecule that has an electron pair that may be donated in bonding to an electrophile is called a ______

<p>nucleophile</p> Signup and view all the answers

Hybridization is the term applied to the mixing electrons of atomic unequivalent orbitals to generate a set of new equivalent ______ orbitals.

<p>hybrid</p> Signup and view all the answers

SP3 hybridization involves the mixing of the electron in 2S with three electrons of 2P to produce four ______ hybrid orbitals.

<p>SP3</p> Signup and view all the answers

Carbon radicals have only seven valence electrons and are considered electron ______.

<p>deficient</p> Signup and view all the answers

Examples of nucleophiles include substances like R-NH2 and ______-OH.

<p>R-O</p> Signup and view all the answers

Ethylene molecule contains a C=C and has ______ geometry.

<p>planar</p> Signup and view all the answers

In sp2 hybridization, only 2Px and 2Py orbitals combine with the 2S orbital while the 2Pz orbital remains ______.

<p>unchanged</p> Signup and view all the answers

Acetylene molecule has a ______ geometry, containing a carbon-carbon triple bond.

<p>linear</p> Signup and view all the answers

The total number of ______ bonds formed by the unhybridized 2Py and 2Pz orbitals in acetylene is two.

<p>pi</p> Signup and view all the answers

A compound having a bond angle of 180° is an ______.

<p>Alkyne</p> Signup and view all the answers

What type of chemical bonding will be found in ______ oxide?

<p>magnesium</p> Signup and view all the answers

The total number of tertiary ______ found in the compound is [4].

<p>carbons</p> Signup and view all the answers

Which among the following compounds cannot form ______ bond?

<p>hydrogen</p> Signup and view all the answers

Flashcards

Aufbau Principle

In the ground state of an atom or ion, electrons fill subshells of the lowest available energy first, then higher energy subshells.

Monovalent Atom

An atom that forms one chemical bond.

Covalent Bond (Carbon)

Carbon forms four covalent bonds.

Lone Pair

A pair of valence electrons that are not shared with another atom.

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Molecular Shape (no lone pairs)

The arrangement of atoms in a molecule, where lone pairs of electrons on the central atom are not considered.

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Tetrahedral

A molecular geometry with 4 bonding groups, arranged around a central atom at angles of approximately 109.5 degrees.

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Trigonal Planar

A molecular geometry with 3 bonding groups, arranged around a central atom at angles of approximately 120 degrees.

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Linear

A molecular geometry with 2 bonding groups, arranged in a straight line (180 degrees) around a central atom.

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Isomer

Different compounds with the same molecular formula but different structural arrangements.

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Structural Formula

A visual representation of the arrangement of atoms and bonds in a molecule.

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Resonance

A way to describe the delocalization of pi electrons in a molecule or ion, where bonding cannot be shown by a single structure.

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Primary Carbon (1°)

A carbon atom bonded to only one other carbon atom.

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Secondary Carbon (2°)

A carbon atom bonded to two other carbon atoms.

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Van der Waals Forces

Weak attractive forces between atoms and molecules.

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Dipole-Dipole Attraction

Attractive forces between the positive and negative ends of polar molecules.

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Hydrogen Bond

Strong dipole-dipole attraction between a hydrogen atom bonded to a highly electronegative atom (N, O, or F) and another electronegative atom.

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Reaction Arrow

Shows the change in a reaction, from reactants to products.

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Equilibrium Arrow

Represents a reversible reaction where products can revert to reactants and vice-versa.

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Resonance Arrow

Shows the movement of electrons within a molecule to form different resonance structures.

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Reactive Intermediate

Short-lived species formed during a reaction, but not a final product.

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Electrophile

Electron-deficient species attracted to electron-rich species.

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Nucleophile

Electron-rich species that donates electrons.

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Hybridization

Mixing of atomic orbitals to form new hybrid orbitals.

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sp3 hybridization

Mixing of one s and three p atomic orbitals to form four equivalent sp3 hybrid orbitals.

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sp3 hybridization Example

CH4(methane) is an example of sp3 hybridization. Four sigma bonds are created.

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Electrophile Example

A species with a positive charge or positive end of a polar bond that is attracted to electron-rich groups.

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Covalent Bond Stability

Compounds with strong covalent bonds are more stable than those with weaker bonds.

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Electronic Effects

Electron distribution at reaction sites (functional groups) significantly impacts reactions.

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Inductive Effect

A type of electronic effect related to electron shifting.

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Resonance Effect

Another type of electronic effect that depends on resonance structures.

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Steric Effects

Atoms' spatial arrangement; crowding creates unfavourable 'steric hindrance'.

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Steric Hindrance

The difficulty of reactions due to the spatial arrangement of atoms.

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Solvent Effects

The solvent can affect how reactions proceed.

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Reaction Mechanism

A detailed description of bond changes during a reaction.

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Full Head Arrow

In reaction mechanisms, a full head arrow shows a complete electron pair movement.

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Half Headed Arrow

In reaction mechanisms, a half-headed arrow shows a single electron movement.

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Homolysis

When a bond breaks, and each fragment gets one electron.

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Heterolysis

When a bond breaks, and both electrons go to one fragment.

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Electron Rich Species

A species that has a high concentration of electrons

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Reaction

A process in which one or more substances are changed into different substances.

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SP2 Hybridization (C2H4)

Ethylene's carbon atoms use three hybrid orbitals (sp2) to form bonds, while the remaining unhybridized p-orbital forms a pi bond.

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SP Hybridization (C2H2)

Acetylene's carbon atoms form two sp hybrid orbitals for sigma bonds and two unhybridized p-orbitals for pi bonds.

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Ionic Bond

Bond formed by electrostatic attraction between oppositely charged ions.

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Covalent Bond

Bond formed by sharing electrons between atoms.

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Fluorine Electronic Configuration

Fluorine (atomic no. 9) has 2 electrons in the first shell and 7 in the second shell.

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Magnesium Oxide Bonding

Magnesium Oxide has an ionic bond

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Electrophile

A species that accepts an electron pair.

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Trivalent Atom

An atom that can form three bonds.

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Hydrogen Bond Donor

A molecule with a hydrogen atom bonded to a highly electronegative atom (N, O, or F).

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Alkyne Geometry

180° bond angle, linear. It forms triple bonds.

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Carbon Bonds

Carbon typically forms 4 covalent bonds.

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Intermolecular forces in dimethyl ether

Dipole-dipole interactions are the dominant intermolecular forces in dimethyl ether.

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Hydrogen bond formation

Hydrogen bonds form between molecules containing a hydrogen atom bonded to a highly electronegative atom (e.g., oxygen, nitrogen) and another electronegative atom in a separate molecule.

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Solubility in water

Organic compounds with polar groups (able to form hydrogen bonds) are more soluble in water; nonpolar compounds (no hydrogen bonding capability) are generally insoluble.

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Hydrophilic moiety

The polar, hydrogen-bonding part of a molecule, which interacts favorably with water.

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Hydrophobic moiety

The nonpolar, non-hydrogen-bonding part of a molecule, which tends to avoid interaction with water.

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Chemical Reaction

A process where reactants transform into different products.

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Reactant

The substance undergoing change in a chemical reaction.

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Product

The resulting substance after a chemical reaction.

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Reaction Conditions

Environmental factors affecting the rate and outcome of a chemical reaction (e.g., temperature, pressure, catalysts, solvent).

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Catalyst

A substance that speeds up a chemical reaction without being consumed in the process.

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Addition Reaction

A reaction where the number of sigma bonds increases, usually by the conversion of a pi bond to sigma bonds.

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Elimination Reaction

A reaction where the number of sigma bonds decreases, often creating a new pi bond.

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Substitution Reaction

A reaction where one atom or group is replaced by another.

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Rearrangement Reaction

A reaction that produces an isomer by rearranging atoms or groups within the molecule.

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Oxidation

A reaction where a carbon atom loses hydrogen atoms or gains bonds to more electronegative atoms.

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Reduction

A reaction where a carbon atom gains hydrogen atoms or loses bonds to more electronegative atoms.

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Study Notes

Pharmaceutical Organic Chemistry I PC101 - Introduction

  • Course name: Pharmaceutical Organic Chemistry I PC101
  • Instructor: Mona S. El-Zoghbi, Ph.D. Pharm. Sc.
  • Contact: [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 and their IUPAC names,
  • Students will be able to explain alkanes, alkenes, alkynes, and alkyl halides including nomenclature, physical and chemical properties, and reactions.
  • Students will be able to classify different reaction mechanisms.
  • Students will be able to describe fundamental principles and applications of stereochemistry, stereo-dynamics, hydroxyl, and carbonyl compounds.
  • Students will be able to recognize principles of aromaticity and benzenoid compounds.

Quiz Questions

  • The Pauli Exclusion rule states electrons fill subshells of lowest available energy, then higher energy.
  • Fluorine is a monovalent atom.
  • Carbon forms four covalent bonds.

Lone Pairs

  • Lone pairs are pairs of valence electrons not shared with another atom.
  • They are found in the outermost electron shell of atoms.

Molecular Shapes

  • Molecular shape/configuration is an important property.

Shapes of Molecules Without Lone Pairs

  • Tetrahedral: 4 bonding groups, 109.5° bond angles
  • Trigonal: 3 bonding groups, 120° bond angles
  • Linear: 2 bonding groups, 180° bond angle

Isomers

  • Isomers are different compounds with the same molecular formula.
  • Example isomers of C5H12 are: pentane, 2-methylbutane, 2,2-dimethylpropane.

Structural Formulas for C4H10O Isomers

  • Various structural formulas are shown for C4H10O.

Resonance

  • Describes delocalized pi electrons in molecules or polyatomic ions where bonding cannot be represented by a single structure.
  • The double-headed arrow represents resonance.

Different Groups of Carbon Atoms

  • Primary (1°): bonded to 1 other carbon.
  • Secondary (2°): bonded to 2 other carbons.
  • Tertiary (3°): bonded to 3 other carbons.
  • Quaternary (4°): bonded to 4 other carbons.

Intermolecular Forces

  • Atoms/molecules are weakly attracted to each other.
  • Weak forces called van der Waals attraction forces exist.
  • Without them, all matter would be gaseous.

Dipole-Dipole Attraction

  • Attracive forces between the positive end of a polar molecule to the negative end of another polar molecule.

Hydrogen Bonding

  • Electrostatic attraction between a hydrogen (H) and electronegative atoms (N, O, F) and another adjacent atom bearing a lone pair of electrons.
  • Hydrogen bonding is stronger than dipole-dipole forces but weaker than covalent bonding.

Hydrogen Bonding Accounts

  • Ethyl alcohol has a much higher boiling point (78.5°C) than dimethyl ether (24.9°C) due to hydrogen bonding.

Solubility of Organic Compounds in Water

  • Many organic compounds (alkane etc) are nearly insoluble in water
  • Organic compounds that are water-soluble such as ethanol and acetone usually contain hydrogen bond acceptors or donors

Chemical Reactions

  • A transformation of reactants into reaction products
  • A reactant is an organic compound undergoing change.
  • A product is the final result of the chemical reaction
  • Reaction conditions (temperature, pressure, catalysts, solvent) optimize the reaction.
  • Catalysts accelerate the reaction rate without being consumed.

Classes of Organic Chemical Reactions

  • Addition: the number of σ-bonds increases, usually at the expense of Ï€-bonds.
  • Elimination: the number of σ-bonds decreases, and new Ï€-bonds are created.
  • Substitution: one atom or group is replaced by another.
  • Rearrangement: generates an isomer; the number of bonds does not change.

Mechanism of Organic Reactions

  • Detailed description of structural/bonding changes.
  • Involve curved arrows for understanding bond breaking/formation.
  • Full head arrow indicates electron pair movement.
  • Half head arrow indicates single electron movement.

Homolysis vs Heterolysis

  • Homolysis: a covalent bond breaks, each fragment receives one electron.
  • Heterolysis: a covalent bond breaks, both electrons stay with one fragment.

Reaction Mechanism - General Overview

  • Curved arrows are used in drawing mechanisms.

Reactive Intermediates

  • Charged: Carbocation, Carbanion
  • Uncharged: Radical, Carbene

Electrophiles and Nucleophiles

  • Electrphile: Electron-deficient atom/molecule attracted to electron-rich species.
  • Nucleophile: Electron-rich atom/molecule attracted to electron-deficient species.

Hybridization

  • Combining atomic orbitals to create hybrid orbitals.
  • SP3 hybridization: Found in CHâ‚„, tetrahedral geometry.
  • SP2 hybridization: Found in Câ‚‚Hâ‚„, planar geometry; double bonds are formed from sideway overlapping of unhybridized orbitals.
  • SP hybridization: Found in Câ‚‚Hâ‚‚; linear geometry; triple bonds are formed from sideway overlapping of unhybridized orbitals.

Practice Exercises

  • Various exercises and quiz questions that appear throughout, are included.

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