OChem, WSU CHEM 345

Erm, Whatever

Alkane

pKa 50

Alkene

pKa 45

Alkyne

pKa 25

Amine

pKa

Alyls

pKa 45

Nitrile

pKa 25

Imine

pKa

Aniline

pKa 30

Ammonia

pKa 35

Water

pKa 15

Alcohol

pKa 15

Cyclopentadiene

pKa 15

Ether

pKa

Epoxide

pKa

Haloalkane

pKa

Phenol

pKa

Bicarbonate

pKa 10

Thiol

pKa 10

β-Keto Carbonyls

pKa 10

Aldehyde

pKa 20

Ketone

pKa 20

Amide

pKa 15

Carboxylic Acid

pKa 5

Benzene Ring

pKa

Carbonic Acid

pKa 5

Alphatic Ammonium Ions

pKa 10

Aromatic Ammonium Ions (Anilinium & Pyridinium Ions)

pKa 5

Ester

pKa 25

Acyl Halide

pKa

Acid Anhydride

pKa

Aromatic Hydrocarbon

pKa

Aromatic Alcohol

pKa

Aromatic Amine

pKa

Haloarene

pKa

Aromatic Carboxylic Acid

pKa

Aromatic Aldehyde

pKa

Aromatic Ketones

pKa

Nitrobenzene

pKa

Hydrohalic Acids

pKa ≤0

Nitric Acid

pKa ≤0

Sulfuric Acid

pKa ≤0

Phosphoric Acid

pKa ≤0

Structural formula

Hella detailed

Parent names based on carbons, 1-10 (end in “ane, ene, or yne”):

meth, eth, prop, but, pent, hex, hept, oct, non, & dec

Suffixes after parent name based on bond type:

ane (single), ene (double), & yne (triple)

Butyl

ethyl

Tert-butyl

Propyl

methyl

sec-butyl

Isobutyl

Relationship between pKa, Ka, and strength

Strength grows as pKa gets lower and Ka get higher. pKa = -log(Ka)

H-H equation

pH = pKa + log(conj base/acid)

Periodic table trends

Acid-base equilibrium favor

Depends on weakest acid, if weak acid can be made (base stronger that acid) than the reaction will occur

Hydrocyanic acid

pka 10

pi () v sigma () bond

Along the length v head to head

Formula to get number of H’s relative to carbon to represent an alkane

2(number of C) + 2

Draw trans-1-2-dichlomocyclohexane

Draw Cis-1,3-dichlomocyclohexane, equatorial are more stable bc axial strain

A twist switches axial and equatorial but not up or down

Statistics but stfu. Calculate Z score

(Value minus average) over standard deviation

Stats but shhhhh: Describe a cofounder

A variable related to both treatment and outcom

Allyl

Vinyl

Electrophile v nucleophile

The more positive one that wants the (-) v the more negative one that wants the (+)

Syn-dihydroxylation) v Chlor/Halo/Bromination

KMnO4/PH₈ →, cis addition of 2OH^- v X₂ →, trans addition of 2X^-

Epoxidation

mCPBA →, Use an O to give a party hat in a cis way

Hydrohalogenation

HX→, Adding H⁺ and a halogen^-

Hydration of alkenes

H₂O →, (Add OH^- and H⁺)

Hydrogenation

H₂/(Pd/C) →, adds 2H⁺ or two (visible) D⁺ to remove double and triple bonds. In a cis way

Tortional v steri v ring strain

Forcing e- clouds to be closer to each (usually when eclipsing), alleviated with rings and puckered configuration; v grows with larger groups moving closer to main body of molecule; v forced to be close to each other bc of being in a ring, grows if all on same plane

Benzene pre-fix names based on sub placements

Ortho (1 & 2), meta (1 & 3), para (1 & 4)

Groups that activate ring towards substitution (activating)

Have no double or triple bonds. Ortho, para-directing. Wins if conflicted with a withdraw e- groups because it speeds up the reaction and makes more of itself faster.

Groups that withdraw e- through resonance (deactivating)

Have double and/or triple bonds. Meta directing

Ortho, para-directing groups

Atom next to the ring has lone pairs (also methyl and carbon groups???)

KMnO4/H₃O →, in reactions of benzene with a substitute

Adds a carboxylic acid or turns isopropyl into carboxylic acid??? (R-(C=O)-OH)

Ortho

Meta

Para

Chiral/chirality centers v achiral

4 dif groups on C as to be nonsuperimposable with its mirror image v does have perfect symmetry in some way

Benzene as a substitute

aka phenyl when it’s on a chain of 7C or more

When naming a ring with its own name

Start numbering at the substitute that gives its name then only number the others

Benzyl group

Benzyl ‘name of ‘R‘

Toluene

Phenol

Anisole

Aniline

Benzoic acid

Benzaldehyde

Acetophenone

Styrene

Sulfonation of benzene

SO₃/H₂SO₄→

Nitration of benzene

HNO₃/H₂SO₄→

Friedal-Crafts Alkylation

Adding a carbon group using a halide as glue

Friedal-Crafts Acylation

Adding an acyl group using a halide as glue

Deactivating but ortho, para-directing

Halogens

Bromination (EAS) of benzene

Br₂/FeBe₃→

Chlorination (EAS) of benzene

Cl₂/AlCl₃→