Notes in Organic Chemistry I

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Published	09/17/2023	Each element is distinguished by its atomic number ({{c1::Z}}), which {{c2::equals the number of protons in the nucleus}}.
Published	09/17/2023	{{c1::Isotopes}} are {{c2::atoms of the same element that have different atomic masses.}}
Published	09/17/2023	{{c1::Electronegativity}} is a measure of an atom's {{c2::attraction for electrons.}}
Published	09/17/2023	Electronegativity {{c1::increases}} left→right across the periodic table and {{c1::decreases}} top→bottom down the periodic table.
Published	09/17/2023	{{c1::Unshared electron pairs}} are also called {{c2::lone pairs.}}
Published	09/17/2023	Atoms of 2nd row elements can have no more than {{c1::8}} valence electrons {{c1::(an octet).}}
Published	09/17/2023	The octet rule {{c1::doesn't}} apply to elements in the 3rd row and beyond.
Published	09/17/2023	{{c1::Formal charge}} is {{c2::the charge assigned to an atom within a structure.}}
Published	09/17/2023	To calculate formal charge for an atom, subtract {{c1::the number of electrons an atom "owns"}} from {{c2::the atom's group number.}}
Published	09/17/2023	{{c1::Isomers}} are {{c2::different compounds with the same molecular formula.}}
Published	09/17/2023	{{c1::Constitutional isomers}} have the same molecular formula, but different connectivity.
Published	09/17/2023	Constitutional isomers have the same {{c1::molecular formula}}, but different {{c1::connectivity.}}
Published	09/17/2023	{{c1::Heteroatoms}} are {{c2::any atoms that are not carbon or hydrogen.}}
Published	09/17/2023	The letter '{{c1::X}}' is used to symbolize {{c2::a generic halogen.}}
Published	09/17/2023	Ions with a {{c1::positive or negative charge on a C atom}} are {{c2::unstable}}, but can be formed and are important because {{c3::they are highly re…
Published	09/17/2023	{{c1::Resonance structures}} have the same {{c2::placement of atoms}}, but a different arrangement of {{c2::electron and/or charge.}}
Published	09/17/2023	{{c1::Resonance hybrids}} are the true structure of molecules with multiple resonance structures, and behave as a composite of all forms.
Published	09/17/2023	{{c1::Delocalization}} adds {{c2::stability.}}
Published	09/17/2023	Never, ever, ever draw an {{c1::arrow}} from a {{c2::positive charge}}!
Published	09/17/2023	Positive charges can reflect a {{c1::deficiency of electron density}} that influences how nearby electrons behave.
Published	09/17/2023	The resonance structure that is {{c1::more stable}} is the {{c2::major contributor}} to the hybrid.
Published	09/17/2023	Resonance structures are stabilized by having {{c1::more bonds}}, {{c1::fewer charges}}, and/or {{c1::all octets filled}}. If all these features are e…
Published	09/17/2023	What's the formal charge of a carbon atom with three single bonds?
Published	09/17/2023	What's the formal charge of a nitrogen atom with four single bonds?
Published	09/17/2023	What's the formal charge of an oxygen atom with three bonds and one lone pair?
Published	09/17/2023	What's the formal charge of a halogen with two bonds and two lone pairs?
Published	09/17/2023	What's the formal charge of Boron with three bonds?
Published	09/17/2023	What's the formal charge of a carbon atom with four bonds?
Published	09/17/2023	What's the formal charge of nitrogen with three bonds and one lone pair?
Published	09/17/2023	What's the formal charge of oxygen with two bonds and two lone pairs?
Published	09/17/2023	What's the formal charge of a halogen with one bond?
Published	09/17/2023	What's the formal charge of boron with four bonds?
Published	09/17/2023	What's the formal charge of a carbon atom with three bonds and a lone pair?
Published	09/17/2023	What's the formal charge of nitrogen with two bonds and two lone pairs?
Published	09/17/2023	What's the formal charge of an oxygen atom with one bond and three lone pairs?
Published	09/17/2023	An atom with {{c1::two groups}} will have {{c2::linear}} geometry and a bond angle of {{c2::180°}}.
Published	09/17/2023	An atom with {{c1::three groups}} will have {{c2::trigonal planar}} geometry and a bond angle of {{c2::120°}}.
Published	09/17/2023	An atom with {{c1::four groups}} will have {{c2::tetrahedral}} geometry and a bond angle of {{c2::109.5°}}.
Published	09/17/2023	In NH3, one of the "groups" on N is a lone pair. The atoms, therefore, form a {{c1::trigonal pyramid}}.
Published	09/17/2023	In H2O, two of the four "groups" on the O are lone pairs. The atoms of H2O appear in a {{c1::bent}} shape.
Published	09/17/2023	{{c2::s}}-orbital: a {{c3::sphere}} of electron density; {{c1::lower}} in energy than other orbitals of the same level
Published	09/17/2023	{{c1::p}}-orbital: has a {{c2::dumbbell}} shape; contains a node of electron density at the nucleus; {{c3::higher}} in energy than an {{c1::s}}-orbita…
Published	09/17/2023	An orbital can only hold up to {{c1::2}} electrons.
Published	09/17/2023	An atomic orbital gets involved in bonding by {{c1::overlapping with an orbital from a neighboring atom}} to form {{c2::molecular orbitals}}.
Published	09/17/2023	When two atomic orbitals mix, we get two new orbitals: a {{c1::bonding}} molecular orbital and an {{c1::antibonding}} molecular orbital.
Published	09/17/2023	Aside from the 1s orbital, each element in the 2nd row has {{c1::four}} other orbitals available to accept electrons: {{c1::one}} 2s and {{c1::three}}…
Published	09/17/2023	Atoms like carbon do not use {{c1::pure s and pure p orbitals}} in forming single bonds. Instead, they {{c2::reorganize/mix their orbitals to form hyb…
Published	09/17/2023	{{c1::Hybridization}} is {{c2::the mathematical combination of two or more different atomic orbitals}} to form {{c2::the same number of hybrid orbital…
Published	09/17/2023	Mixing an atom's 2s and 2p orbitals produces {{c1::four sp3 orbitals}} {{c1::(one part s, three parts p).}}
Published	09/17/2023	The mathematical shape of an sp3 orbital involves {{c1::one large lobe}} and {{c1::one small lobe}}.
Published	09/17/2023	Four sp3 orbitals allow atoms to form {{c1::four equivalent sigma bonds}} in a {{c2::tetrahedral shape}}.
Published	09/17/2023	One 2s orbital and two 2p orbitals could mix to form {{c1::three sp2 hybrid orbitals}} {{c1::(leaving one 2p orbital unhybridized)}}.
Published	09/17/2023	One 2s orbital and one 2p orbital could mix to form {{c1::two sp hybrid orbitals}} {{c1::(leaving two 2p orbitals unhybridized)}}.
Published	09/17/2023	The hybridization of an atom in a molecule depends on {{c1::the number of "groups" around it.}}
Published	09/17/2023	If there are {{c1::two groups}} around an atom, there will be {{c2::two sp hybrid}} orbitals.
Published	09/17/2023	If there are {{c1::three groups(orbitals)}} around an atom, there will be {{c2::three sp2 hybrid}} orbitals.
Published	09/17/2023	If there are {{c1::four groups(orbitals)}} around an atom, there will be {{c2::four sp3 hybrid}} orbitals.
Published	09/17/2023	Unhybridized 2p orbitals overlap to form {{c1::a pi bond.}}
Published	09/17/2023	A carbon atom will hybridize {{c1::sp2}} instead of {{c2::sp3}} when there are {{c3::only three groups around it.}}
Published	09/17/2023	A carbon atom will hybridize {{c1::sp}} instead of {{c2::sp3}} when there are {{c3::only two groups around it.}}
Published	09/17/2023	Triple bonds are composed of {{c1::one}} {{c2::sigma bond}} and {{c1::two}} {{c2::pi bonds}}.
Published	09/17/2023	Bond length {{c1::increases}} down a column of the periodic table as {{c2::the size of an atom increases}}.
Published	09/17/2023	Significantly longer bonds tend to be {{c1::somewhat weaker}}.
Published	09/17/2023	Bonds between two electrongetative atoms tend to be {{c1::somewhat weaker}}.
Published	09/17/2023	Pi(π) bonds are {{c1::weaker}} than sigma(σ) bonds.
Published	09/17/2023	As the percentage of {{c1::s-character increases}}, a hybrid orbital holds its electrons closer to the nucleus on average and a bond involving the orb…
Published	09/17/2023	{{c2::Hydrocarbons}} contain {{c1::only hydrogen and carbon atoms}}.
Published	09/17/2023	{{c1::Alkanes}} are hydrocarbons with {{c2::single bonds only}}.
Published	09/17/2023	{{c1::Alkanes}} are very {{c2::unreactive}} and are not considered to contain any functional groups.
Published	09/17/2023	{{c1::Alkanes}} use the suffix {{c2::-ane}}.
Published	09/17/2023	{{c1::Alkenes}} are hydrocarbons with at least one {{c2::C=C double bond}}.
Published	09/17/2023	{{c1::Alkynes}} are hydrocarbons with at least one {{c2::C≡C triple bond}}.
Published	09/17/2023	{{c2::Alkenes}} use the suffix {{c1::-ene}}.
Published	09/17/2023	{{c2::Alkynes}} use the suffix {{c1::-yne}}.
Published	09/17/2023	{{c1::Aromatic hydrocarbons}} contain a cyclic array of alternating pi bonds. The most common example is {{c2::benzene}}.
Published	09/17/2023	{{c1::Heteroatoms}} are {{c2::atoms other than C or H.}}
Published	09/17/2023	Oxygen, nitrogen, and halogens have {{c1::lone pairs of electrons}}, but can also create {{c2::electron deficient sites on attached carbons or hydroge…
Published	09/17/2023	Pi(π) bonds are sites of {{c1::accessible electron density}}. These areas can be attacked by {{c2::highly electron-deficient species}} and {{c2::broke…
Published	09/17/2023	{{c1::Aromatic compounds}} are called {{c2::aryl groups}}.
Published	09/17/2023	The letter {{c1::R}} is used to represent {{c2::a general, unspecified alkyl group}}.
Published	09/17/2023	When a {{c1::benzene ring}} is bonded to something to form a larger molecule, it comprises a functional group called a {{c2::phenyl group}}.
Published	09/17/2023	When a benzene ring is attached specifically to a {{c1::CH2}}, it is called a {{c2::benzyl group}}.
Published	09/17/2023	What is an alkyl halide?
Published	09/17/2023	What is a halo group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	{{c1::Alkyl halides}} contain a {{c2::halogen atom}} bonded to an {{c2::sp3 -hybridized carbon}} of an alkyl group.
Published	09/17/2023	A {{c1::primary (1°)}} alkyl halide has {{c2::1}} R-group attached to the carbon that holds the halogen.
Published	09/17/2023	A {{c1::secondary (2°)}} alkyl halide has {{c2::2}} R-groups attached to the carbon that holds the halogen.
Published	09/17/2023	A {{c1::tertiary (3°)}} alkyl halide has {{c2::3}} R-groups attached to the carbon that holds the halogen.
Published	09/17/2023	Is this alkyl halide primary, secondary, or tertiary?
Published	09/17/2023	Is this alkyl halide primary, secondary, or tertiary?
Published	09/17/2023	Is this alkyl halide primary, secondary, or tertiary?
Published	09/17/2023	{{c2::Vinyl}} halides have a halogen bonded to a {{c1::C=C}}.
Published	09/17/2023	{{c2::Aryl}} halides have a halogen bonded to a {{c1::benzene ring}}.
Published	09/17/2023	{{c2::Allylic}} halides have a halogen bonded to a {{c1::carbon atom adjacent to a C=C}}.
Published	09/17/2023	{{c2::Benzylic}} halides have a halogen bonded to a {{c1::carbon atom adjacent to a benzene ring}}.
Published	09/17/2023	Five patterns to recognize for resonance structures:{{c1::1. A lone pair next to a pi bond.}}{{c2::2. A lone pair next to C+.}}{{c2::3. A pi bond next…
Published	09/17/2023	Why are there different classes of halides?
Published	09/17/2023	Alcohols are analogous to {{c1::water}}, but {{c2::have one H replaced by an R}}.
Published	09/17/2023	Is this a primary, secondary, or tertiary alcohol?
Published	09/17/2023	Is this a primary, secondary, or tertiary alcohol?
Published	09/17/2023	Is this a primary, secondary, or tertiary alcohol?
Published	09/17/2023	{{c1::Phenols}} are like {{c2::alcohols}}, but with {{c3::the OH}} directly connected to {{c3::a benzene ring}}.
Published	09/17/2023	The properties of phenols are different from alcohols because of the {{c1::adjacent pi-bond system (resonance)}}.
Published	09/17/2023	{{c1::Ethers}} are analogous to {{c2::alcohols}}, except that {{c3::both H's of H2O}} are replaced by {{c3::R groups}}.
Published	09/17/2023	Here we have a(n) {{c1::acyclic ether.}}
Published	09/17/2023	Here we have a(n) {{c1::cyclic ether.}}
Published	09/17/2023	The lack of {{c1::OH}} has a major impact on the chemistry of {{c2::ethers}}.
Published	09/17/2023	For {{c2::amines,}} the 1°/2°/3° classification is based on the number of R groups {{c1::directly attached to the N}}.
Published	09/17/2023	Amines may be {{c1::cyclic}} or {{c1::aromatic}}.
Published	09/17/2023	A {{c1::C=O}} unit is called a {{c2::carbonyl group}}. {{c2::Carbonyl groups}} are found within a set of functional groups (are not an "offi…
Published	09/17/2023	A C=O unit is {{c1::polar}}- the carbonyl C is {{c2::electrophilic}}, and the lone pairs on O are {{c2::nucleophilic}}.
Published	09/17/2023	The C=O group contains a {{c1::π bond}} that is more easily broken than the C-O σ bond.
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's the functional group?
Published	09/17/2023	What's this functional group?
Published	09/17/2023	{{c1::Biomolecules}} are {{c2::organic compounds found in biological systems}}. Most types contain multiple functional groups.
Published	09/17/2023	Polar bonds are created by {{c1::a substantial difference in electronegativity between two covalently bonded atoms}}.
Published	09/17/2023	{{c1::Electron-rich}} reagents may attack{{c2:: 𝛿+ sites}} in a polar bond.
Published	09/17/2023	{{c1::Electron-deficient}} reagents may attack {{c2::𝛿-}} sites in a polar bond.
Published	09/17/2023	{{c1::Ionic compounds}} are much stronger than {{c2::intermolecular forces}} that occur between covalent molecules.
Published	09/17/2023	Dispersion forces are caused by {{c1::temporary dipoles}} in a molecule, which are created by {{c2::a molecule's electron density being shifted around…
Published	09/17/2023	{{c1::Dispersion forces}} are the only type of attractive forces displayed by {{c2::nonpolar compounds}} (such as hydrocarbons).
Published	09/17/2023	All compounds experience {{c1::dispersion}} forces.
Published	09/17/2023	{{c1::Polarizability}} is a measure of {{c2::how easily the electron cloud around an atom or molecule responds to changes in its environment}}.
Published	09/17/2023	Larger atoms/molecules are {{c1::more}} polarizable than smaller atoms/molecules.
Published	09/17/2023	Molecules with more surface area experience {{c1::more}} dispersion forces.
Published	09/17/2023	{{c1::Dipole-dipole}} interactions are {{c2::attractive forces between the permanent dipoles of two polar molecules}}.
Published	09/17/2023	Dipole-dipole forces are {{c1::stronger}} than dispersion forces.
Published	09/17/2023	{{c1::Hydrogen bonding}} occurs when an H atom directly bonded to an O, N, or F is electrostatically attracted to a lone pair on an O, N, or F atom in…
Published	09/17/2023	Hydrogen bonding is so strong because the H bears {{c1::a significant 𝛿+ charge}} and can {{c1::get very close to the N, O, or F atom}} on the ot…
Published	09/17/2023	Strength of intermolecular forces:{{c1::dispersion}} < {{c1::dipole-dipole}} < {{c1::ion-dipole}} < {{c1::hydrogen bonding}}
Published	09/17/2023	Covalent bonds are about {{c1::20}} times stronger than H- bond intermolecular forces.
Published	09/17/2023	The stronger the intermolecular forces, the {{c1::higher}} the boiling point and melting point of a molecule.
Published	09/17/2023	The larger the {{c1::surface area}} and {{c1::more polarizable}} the atoms, the {{c2::higher}} the boiling point.
Published	09/17/2023	Given the same class of compound, the {{c1::more compact}} and {{c1::symmetrical}} the compound, the {{c2::higher}} the melting point.
Published	09/17/2023	Compactness and symmetry are more relevant to melting point than boiling point, because {{c1::they impact how well the molecules fit together in a cry…
Published	09/17/2023	The melting point for covalent molecules are influenced by {{c1::functional groups present}}.
Published	09/17/2023	Solubility is the extent to which a compound (a {{c2::solute}}) {{c3::dissolves in a liquid}} (a {{c1::solvent}}).
Published	09/17/2023	Compounds dissolve in solvents that display similar kinds of {{c2::intermolecular forces}}→"{{c1::like}} dissolves like"
Published	09/17/2023	Many organic solvents are {{c1::nonpolar}} or {{c1::weakly polar}}.
Published	09/17/2023	Most ionic compounds are soluble in {{c1::water}}, but insoluble in {{c1::organic solvents}}.
Published	09/17/2023	An organic compound will be significantly H2O-soluble only if it contains {{c1::one functional group capable of H-bonding with H2O for every five C at…
Published	09/17/2023	Would you predict butane to be soluble in CCl4 and/or H2O?
Published	09/17/2023	Would you predict acetone to be soluble in CCl4 and/or H2O?
Published	09/17/2023	Solubility does not necessarily mean {{c1::miscibility}}. For example, n-butanol (CH3CH2CH2CH2OH) dissolves in H2O, {{c2::but only to a limited extent…
Published	09/17/2023	To dissolve an ionic compound, the strong ion-ion interactions must be replaced by {{c1::many weaker ion-dipole interactions}}.
Published	09/17/2023	The {{c1::nonpolar}} part of a molecule {{c1::that is not attracted to H2O}} is said to be {{c2::hydrophobic}}.
Published	09/17/2023	The {{c1::polar}} part of a molecule that {{c1::can hydrogen bond to H2O}} is said to be {{c2::hydrophilic}}.
Published	09/17/2023	Would you expect cholesterol to be water soluble?
Published	09/17/2023	Electron-{{c2::deficient}} sites are referred to as {{c1::electrophilic}}.
Published	09/17/2023	Electron-{{c2::rich}} sites are referred to as {{c1::nucleophilic}}.
Published	09/17/2023	A {{c1::lone pair}} on a heteroatom makes it somewhat electron-rich, and therefore somewhat {{c2::nucleophilic}} and {{c2::basic}}.
Published	09/17/2023	𝝅-bonds are electron rich and therefore somewhat {{c1::nucleophilic}}, and are more {{c2::easily broken}} than σ-bonds.
Published	09/17/2023	Electron-deficient carbons tend to react with {{c1::nucleophiles (:Nu-).}}
Published	09/17/2023	Electron-rich carbons tend to react with {{c1::electrophiles (E+).}}
Published	09/17/2023	Are alkenes expected to be nucleophilic or electrophilic?
Published	09/17/2023	Are alkyl halides expected to be nucleophilic or electrophilic?
Published	09/17/2023	Because they are {{c2::nucleophilic}}, alkenes do not react with {{c1::electron-rich species}} such as OH- or Br-.
Published	09/17/2023	{{c1::Wavelength (λ)}} is {{c2::the distance from one point on a wave to the analagous point on the next wave}}.
Published	09/17/2023	{{c1::Frequency (ν)}} is {{c2::the number of waves passing per unit time.}}
Published	09/17/2023	Frequency is reported in {{c1::cycles per second (s-1)}}, aka {{c1::hertz (Hz)}}.
Published	09/17/2023	The energy (E) of a photon is proportional to its {{c1::frequency (ν)}}. E = {{c2::hν}}, where {{c2::h}} = Planck's constant.
Published	09/17/2023	Energy (E) and wavelength  (λ) are {{c1::inversely}} proportional.
Published	09/17/2023	Frequency (v) and wavelength (λ) are {{c1::inversely}} proportional.
Published	09/17/2023	For absorption of electromagnetic radiation to occur, the energy must {{c1::match the energy difference between two energy states in the molecule}}.
Published	09/17/2023	Ultraviolet (UV)-visible light causes {{c1::electronic}} excitation.
Published	09/17/2023	Infrared (IR)-visible light causes {{c1::vibrational}} excitation.
Published	09/17/2023	Different kinds of {{c2::bonds}} vibrate at different frequencies, which occur in the {{c1::IR range}} of the spectrum.
Published	09/17/2023	An {{c1::IR spectrum}} is a plot of the {{c2::percent of transmitted light}} vs {{c2::frequency}}.
Published	09/17/2023	In IR spectra, frequency is given in {{c1::wavenumbers (cm-1)}}.
Published	09/17/2023	Wavenumber is not the same as {{c1::wavelength}}- it is a {{c1::frequency}} term (inverse of wavelength).
Published	09/17/2023	{{c2::Stronger}} bonds (i.e. triple > double > single) vibrate at a {{c1::higher}} frequency ({{c1::higher}} wavenumbers).
Published	09/17/2023	Bonds with lighter atoms vibrate at {{c1::higher}} frequency ({{c1::higher}} wavenumbers).
Published	09/17/2023	The {{c1::fingerprint region}} is the part of an IR spectrum associated with {{c2::single bonds}}. It's a mess, so we don't care about this range.
Published	09/17/2023	{{c1::O-H}} bonds absorb wavenumbers in the {{c2::3600-3200 cm-1}} range with strong/broad intensity.
Published	09/17/2023	{{c1::N-H}} bonds absorb wavenumbers in the {{c2::3500-3200 cm-1}} range with medium intensity.
Published	09/17/2023	{{c1::Csp-H}} bonds absorb wavenumbers in the {{c2::3300 cm-1}} range with medium intensity.
Published	09/17/2023	{{c1::C≡C}} bonds absorb wavenumbers in the {{c2::2250}} cm-1 range with medium intensity.
Published	09/17/2023	{{c1::C≡N}} bonds absorb wavenumbers in the {{c2::2250}} cm-1 range with medium intensity.
Published	09/17/2023	{{c1::C=O}} bonds absorb wavenumbers in the {{c2::1800-1650 (often ~1700)}} cm-1 range with strong intensity.
Published	09/17/2023	{{c1::C=C}} bonds absorb wavenumbers in the {{c2::1650}} cm-1 range with medium intensity.
Published	09/17/2023	{{c1::Benzene rings}} absorb wavenumbers in the {{c2::1600, 1500}} cm-1 range with medium intensity.
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