orgo 1 - exam 1

organic chemistry

involves chemistry of carbon-containing compounds

2nd row elements

organic chemistry more broadly is the chemistry of what elements

can build very complex structures

why is carbon the building block of life

unstable to stable

everything is usually driven by energy shifts from

more stable

atoms engage in bonds when they are _ in molecules rather than as a free atom

covalent bonding

bonding interaction where electron pairs are shared in molecular orbital between atoms

molecular orbital

new orbital formed between atoms in covalent bonding

ionic bond

results from complementary electrostatic interacions

stealing electrons

ionic bonds involve what

differing electronegativity

ionic bonds are usually between two atoms of

steals electron

stronger electronegative atom in an ionic bond

loses electron

weaker electronegative atom in an ionic bond

atomic orbitals

describes the energy of an electron and the region of space it occupies

wavelike

electrons have _ properties

constructive interference

destructive interference

1s v 2s orbital

2p orbital

orbital mixing/bond rotation/bond stretching or compressing

atoms and molecules can interact to become stable in these ways

better covalent bond

the more closely matched atoms are in energy:

conserved

\#atomic orbitals=#molecular orbitals

total number of orbitals in hybridization must be

anti-bonding

second molecular orbital that is destabiliznig

bonding

first molecular orbital that stabilizes interactions between atoms

stabilizes molecule

electrons in the bonding orbital does what to the molecule

weakens molecule

electrons in the anti-bonding orbital does what to the molecule

bond polarity

covalent bonds are not always equal between atoms of differing electronegativity

formal charge

charge from electron count in the structure

resonance structure

stable bonding arrangements can have several arrangements

linear

sp hybridization

trigonal planar

sp2 hybridization

tetrahedral

sp3 hybridization

trigonal bypyramidal

sp3d hybridization

octahedral

sp3d2 hybridization

109\.5

bond angle for tetrahedral hybridization

120

bond angle for trigonal planar hybridization

180

bond angle for linear hybridization

hybrid orbitals

formed when atoms cannot achieve the most stable bonding configuration using their starting set of atomic orbitals, orbitals combine to create new orbitals having characteristics of each contributing orbital

25% s 75%p

sp3 hybrid components

33% s 67%p

sp2 hybrid components

50%s 50%p

sp hybrid components

hybrid orbitals

in organic molecules, the most stable bonding configurations are usually achieved using

sigma bonds

what does not change between resonance structures

localized

designated “area” for electron

delocalized

equal electron sharing throughout molecule

arrows

represent electron movement between resonance structures

double headed arrow

movement of two electrons

hook arrow, single sided arrow

movement of one electron

resonance hybrid

each resonance structure is a contributor of the global picture of how the electrons are actually distributed

stabilizing by delocalization

resonance forms demonstrate that electrons can be further delocalized across multiple atoms in a molecule and reduce the repulsion between electrons

stable (lower energy)

reactions at equilibrium will favor which side

weaker the conjugate base

the stronger the acid, the

stronger acid

the smaller the pKa

exothermic/endothermic

deltaG gives no direct information on how fast the reaction is, rather characterizes the reaction as

reaction rate

the activation barrier/transition state dictates the

activation barrier

the energy of the collision between molecules required to make a reaction

unfavorable equilibrium

deltaG greater than zero

endothermic characterization

favorable equilibrium

deltaG less than zero

small rapid equilibrium from activation energy

exothermic characterization

reaction mechanism

how the electrons move to make and break bonds in a reaction

functional groups

atoms or parts of a molecule that define the properties/reactivity of the overall model

alkanes

molecules composed exclusively of C-C and C-H bonds aka hydrocarbons

C-C and C-H bond stability

why are alkanes inert?

functional groups

because of their stability, alkanes are said to lack

“r”

alkanes can be labeled as this, usually abbreviated as this because they are non reactive and unimportant to the molecule

straight chain/branched

alkane structure types

straight chain

all carbons are apart of the same linear chain, “normal”

branched alkanes

smaller alkyl groups or chains branching off of the larger alkyl carbon chain, tree analogy

isomer

molecules with the same molecular formula but different structural characteristics

constitutional isomer

atoms connected/bonded differently

alkanes

complete molecules of C and H

alkyl groups

alkane parts of larger molecules

normal

n prefix

isomer

i prefix

secondary

s prefix

tertiary

t prefix

alcohols

characterized by a tetrahedral carbon bonded to a hydroxyl group

\-OH

hydroxyl

\-CH3

methyl

methane

ethane

propane

butane

isobutane

alcohols

primary secondary and tertiary denoted by number of carbons attached to the carbon bearing the functional group in

ether

oxygen with two alkyl groups

sp3

hybridization of oxygen in ethers

diethyl ether

unsymmetrical ether

ether with different alkyl groups on either sides

symmetrical ether

ether with same alkyl group on both sides

ethyl methyl ether

amine

nitrogen attached to 1-3 alkyl groupss

sp3

hybridization of nitrogen in amines

amines

primary secondary and tertiary denoted by number of alkyl groups attached to the nitrogen in

carbonyl

carbon-oxygen double bond, components of many functional groups

no

is carbonyl a functional group alone?

aldehyde

ketone

carboxylic acid

conformation

shape or structure

conformer

molecular shape or structure achieved by rotation or partial rotation about one or more bonds

small

energetic barrier in sigma bonds