orgo exam 2 (edited)

Alkyl halide

A compound where a halogen (F, Cl, Br, I) is bonded to an sp3 carbon

Alcohol

A compound with an —OH group attached to an alkyl carbon

Thiol

A compound with an —SH (sulfhydryl) group attached to carbon

Phenol

A compound where —OH is bonded to an aromatic ring

Enol

A compound where —OH is attached to a double-bonded carbon

Ether

A compound with an oxygen bonded to two carbon groups (R–O–R)

Sulfide (thioether)

A compound with sulfur bonded to two carbon groups (R–S–R)

Alpha carbon

The carbon bonded directly to a functional group like halogen or OH

Primary (1°) carbon

A carbon attached to one other carbon

Secondary (2°) carbon

A carbon attached to two other carbons

Tertiary (3°) carbon

A carbon attached to three other carbons

Common naming (alkyl halides)

Name alkyl group + halide (e.g., methyl chloride)

IUPAC naming (alkyl halides)

Halogens treated as substituents (fluoro-, chloro-, bromo-, iodo-)

Common naming (alcohols)

Name alkyl group + "alcohol"

Principal functional group

The group that determines the suffix in IUPAC naming

Principal chain

The longest chain containing the principal functional group

Alkoxy group

An ether substituent (RO–)

Alkylthio group

A sulfide substituent (RS–)

Diol

A compound with two OH groups

Triol

A compound with three OH groups

Heterocyclic compound

A ring containing atoms other than carbon

Epoxide

A three-membered cyclic ether (oxirane)

sp3 hybridization

Tetrahedral geometry (~109.5° bond angle)

Noncovalent interactions

Attractions between molecules that do not involve covalent bonds

Intermolecular attraction

Attractive force between different molecules

Boiling point

Temperature where vapor pressure equals atmospheric pressure

Van der Waals forces

Weak attractions from temporary dipoles (dispersion forces)

Dispersion forces

Attraction from induced dipoles in molecules

Polarizability

How easily an electron cloud can be distorted

Dipole-dipole interactions

Attractions between molecules with permanent dipoles

Hydrogen bonding

Attraction between H bonded to O/N/F and lone pair on another atom

Hydrogen bond donor

Molecule providing hydrogen (O–H, N–H)

Hydrogen bond acceptor

Molecule with lone pairs that accepts hydrogen bond

Boiling point trend

Increases with molecular size and surface area

Branching effect

More branching lowers boiling point

Alcohol boiling points

High due to hydrogen bonding

Melting point

Temperature where solid becomes liquid

Symmetry effect

Higher symmetry → higher melting point

Solute

Substance being dissolved

Solvent

Substance doing the dissolving

Solution

Homogeneous mixture of solute and solvent

Entropy of mixing

Increase in disorder when substances mix

Free energy of solution (ΔGs)

Determines if solution formation is favorable

Favorable solution

ΔGs < 0

Unfavorable solution

ΔGs > 0

Protic solvent

Solvent that can donate hydrogen bonds (water, alcohols)

Aprotic solvent

Solvent that cannot donate hydrogen bonds

Polar solvent

Solvent with large dipole moment

Nonpolar solvent

Solvent with little or no dipole moment

Dielectric constant

Measure of solvent’s ability to separate charges

"Like dissolves like" rule

Polar dissolves polar; nonpolar dissolves nonpolar

Miscible liquids

Liquids that mix in all proportions

Hydrophobic interaction

Nonpolar molecules cluster together in water

Solvation shell

Layer of solvent molecules surrounding solute

Ion pair

Two oppositely charged ions associated in solution

Dissociated ions

Ions fully separated and surrounded by solvent

Charge-dipole interaction

Attraction between ion and polar molecule

Xenobiotic

Foreign substance in a biological system

Amphipathic molecule

Molecule with both polar and nonpolar regions

Phospholipid

Molecule with polar head and nonpolar tails forming membranes

Phospholipid bilayer

Double layer forming cell membranes

Hydrophilic

Water-attracting (polar)

Hydrophobic

Water-repelling (nonpolar)

Ionophore

Molecule that binds and transports ions

Crown ether

Cyclic compound that binds metal cations

Ion channel

Protein that allows ions to pass through membranes

What happens when DMS is added to this alkene during ozonolysis?

Becomes a ketone

What happens when hydrogen peroxide and water (H₂O₂/H₂O) are added to this alkene during ozonolysis?

Also becomes a ketone

What happens when DMS is added to this alkene during ozonolysis?

Forms an aldehyde

What happens to when hydrogen peroxide and water (H₂O₂/H₂O) are added to this alkene during ozonolysis?

Forms carboxylic acid

What happens when DMS is added to this alkene during ozonolysis?

Forms formaldehyde

What happens when hydrogen peroxide and water (H₂O₂/H₂O) are added to this alkene during ozonolysis?

Forms formic acid

What happens during HBr, HCl and HI addition to an alkene?

Halogen goes to the more substituted C

What happens during acid-catalyzed hydration to an alkene?

OH goes to more substituted C

Addition of Cl or Br and OH-OH does what to an alkene?

Goes to the more substituted C if it has two alkyl substituents

Oxymercuration-reduction to an alkene

No rearrangements; adds H and OH; OH goes to the more substituted C

Hydroboration-oxidation to an alkene

Adds H and OH; Anti-markovnikov (H goes to the MORE substituted C while OH goes to the LESS substituted C)

Ozonolysis in an alkene

Cycloaddition to double bond forms ozonide (C-C double bond is broken)

Catalytic hydrogenation to an alkene

adds H₂

HBr, HCl, and HI addition to an alkyne

can occur once or twice to give vinylic halide or geminal dihalide

Hg²⁺ catalyzed hydration in an alkyne?

Adds H and OH; OH goes to the more substituted C; resulting enols convert to ketones

Hydroboration-oxidation in alkynes

Adds H and OH; Anti-Markovnikov (OH is added to the LESS substituted C); resulting enols convert to aldehydes/ketones

Catalytic hydrogenation to an alkyne

H added to each C if poisoned catalyst (Lindlar’s) is used; two H’s to each if no poison present

Achiral

congruent mirror images

Chiral

enantiomers and noncongruent mirror images

Asymmetric carbon

A carbon that has 4 different groups attaches. CHIRAL DOES NOT MEAN ASYMMETRIC CARBON!

What happens if a sample rotates a plane of polarized light clockwise?

Sample is considered dextrorotatory (+) [not related to R/S]

What happens if a sample rotates a plane of polarized light counterclockwise?

Sample is considered levorotatory (-) [not related to R/S]

What can be said about a substance that rotates a plane of polarized light?

The substance is optically active and chiral

Biot’s law

a = [a]cl (optical rotation = specific rotation*concentration*path length)

Racemic mixture

Type of enantiomer mixture that s 50:50; 0 specific rotation; NOT optically active; NOT ACHIRAL

Enantiomeric ratio (ER)

moles of major enantiomer/moles of minor enantiomer

Enantiomeric Excess (EE)

% of the major enantiomer - % of the minor enantiomer

Specific rotation [a] of mixture used to calculate EE

100% x ([a] mixture/[a] pure)

Stereochemical correlation example

Ozonolysis does not break any bonds (absolute configuration is retained); therefore the absolute configuration can be assumed because they have the same relative positions

Diastereomers

Molecule has two or more asymmetric carbons; not mirror images; differ in all physical properties; do not have identical physical properties

Isomers

Have the same molecular formula

Constitutional isomers

different atomic connectivities

Stereoisomers

have identical atomic connectivities

enantiomer properties

noncongruent mirror images