Test 2 Flashcards by Gwyn DeFeo

Hydrocarbons

Composed of hydrogen and carbon

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Saturated hydrocarbons

No pi bonds, alkanes

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IUPAC step 1

Identify the parent chain

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IUPAC step 2

Name the parent chain

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1 carbon

Methane, meth-

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2 carbon

Ethane, eth-

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3 carbons

Propane, prop-

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4 carbons

Butane, but-

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5 carbons

Pentane, pent-

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6 carbons

Hexane, hex-

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7 carbons

Heptane, hept-

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8 carbons

Octane, oct-

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9 carbons

Nonane, non-

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10 carbons

Decane, dec-

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Cyclie alkanes

And cyclo- to beginning of name based off number of carbons.

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IUPAC step 3

Identify side chains, branches. Use -yl instead of -ane for ending

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IUPAC step 4

Identify where branch or side chain is coming off of parent chain. Number from end with first branch.

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IUPAC step 5

List numbered substitutes before the parent name alphabetically (ignore the prefixes)

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Naming bicyclic compounds

count the total carbons in the fused rings
bicyclo- prefix
bracketed numbers

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Constitutional isomers

Same structure that differ in connectivity

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More stable

Give off less energy

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Staggered confirmation

Lowest energy, spread out, most stable

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Eclipsed confirmation

Highest energy , over lapping, least stable

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Anti conformation

Staggered, methyl groups are farthest apart

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Gauche configuration

Staggered, methyl groups experience being next to each other so less stable.

Cyclohexane

- zero ring strain - lowest energy confirmation “chair” - no torsional strain (H staggered)

Axial atoms

Point up straight

Equatorial atoms

Slightly up or down atoms

Chair flips

The result of C-C single bonds rotate

Día I al interactions

Like a gauche interaction

Cis isomers

Two groups on the same side of the ring

Trans isomers

Two groups are on opposite side of a ring

stereoisomers

same molecular formula and constitution but different spatial arrangement of atoms

chiral atoms

bonded to 4 different groups of atoms

enantiomers

Two molecules that are mirror images but are non-identical and non-superimposable.

clockwise

counterclockwise

dash

lowest priority group

fisher projections horizontal lines

forward, wedge

fisher projections vertical lines

back, dash

diastereomers

stereoisomers that are not mirror images.

Going different ways from the double bond, walk like an Egyptian.

going same directions from double bond, zame zide.

breaking a bond

cost energy

creating a bond

releases energy

+ΔH

- endothermic reaction - must take energy from the environment - surroundings cool off

-ΔH

- exothermic reaction - gives energy off - surroundings heat up

entropy

Δs, disorder, randomness, or freedom

spontaneous favors

the forward direction

if ΔStot is positive

the process is spontaneous

ΔG=

ΔHsys-TΔSsys

-ΔG

is a spontaneous reaction

exergonic process

- -ΔG - spontaneous favors products

endergonic process

- +ΔG - nonspontaneous favors the reactants

reaction rate depends on

- reactant concentration - activation energy - temperature - geometry & sterics - any catalyst present

activation energy

energy needed to reach the transition state, want higher energy state

catalyst lower

activation energy

Transition states

peaks

intermediates

vallies

nucleophiles

an atom carrying a formal or partial negative charge and have an available pair of electrons.

electrophiles

an atom carrying a formal or partial positive charge and can accept a pair of electrons.

nucleophilic attack

- the tail of the arrow stars on the electrons - head of the arrow ends on a nucleus

loss of a leaving group

a bond breaks and one atom takes both electrons

proton transfers

an electron pairs steals an H+, arrow points to H+.

carbocation rearrangment

moved over one step to become more stable. Can only occur from an adjacent carbon.

secondary carbocation

- H - R - R

tertiary carbocation

- R -R - R (most stable form)

hydride shift

H moves one step over and + moves.

methide shift

methyl group take one step over, positive charge moves.

rule 1 of arrow pushing

the arrow starts on a pair of electrons ( a bond or a lone pair)

rule 2 of arrow pushing

the arrow ends on a nucleus ( a lone pair forms) or between two nuclei ( a bond forms)

rule 3 of arrow pushing

never give C,N,O, or F more than 8 valence electrons

rule 4 of arrow pushing

draw arrows that follow the four key patterns we outlined.

nucleophilic attack case 1, have a good leaving group

reversible

nucleophilic attack case 2, has a poor leaving group

irreversible

loss of a leaving group

virtually always reversible

proton transfers

reversible

carbocation rearrangements

irreversible

chiral compounds

both chiral atoms are either R or S

Meso compounds

one chiral atom is S while one is R

enantiomers

everything flips

diastereomers

at least one flips but not all