ORGO exam 2 (alkene, A-B rxn)

What goes at the end of an alkene IUPAC nomenclature?

-en- (most likely ene)

how does the IUPAC nomenclature of a alkene change when there is two double bonds in a molecule?

the end will change to -adiene instead

how does the IUPAC nomenclature of a alkene change when there is three double bonds in a molecule?

the ending will change to -atriene instead

what is an alkene

molecule has a double bond, 120 degree bond angle, CnH2n

nucleophile

species that have high abundance of electrons, will donate electrons (Lewis bases)

electrophile

species that have low abundance of electrons and will receive electrons (Lewis acid)

common name for CH2=

methylene

common name for CH2=CH-

vinyl

common name for CH2=CHCH2-

allyl

which isomers are more stable, cis or trans

trans isomers are more stable

the lower the pKa…

the stronger the acid

sulfuric acid pKa (H2SO4)

-10

hydroiodic acid (HI) pKa

-10

hydrobromic acid (HBr) pKa

-9

hydrochloric acid (HCl) pKa

-6

benzenesulfonic acid pKa

-3

Protonated oxygen pKa

-2

hydrofluoric acid (HF) pKa

3

carboxylic acid pKa

5

protonated amines (NH4+) pKa

9

hydrogen cyanide (HCN) pKa

9

thiols (H2S) pKa

9

dicarbonyls pKa

10-13

water pKa

16

alcohol pKa

17

ketone and aldehyde pKa

19

nitrile pKa

25

alkyne pKa

25

sulfoxide pKa

30

amine (NH3) pKa

35

hydrogen pKa

35

alkene pKa

45

alkane pKa

50

what are the requirements for an aromatic structure

planar, cyclic, Huckel’s rule, fully conjugated

Huckel’s rule

4n+2= (answer should be 2,6,10,14,18…)

name the addition reaction

hydrochlorination (hydrohalogenation)

name the addition reaction

hydration

name the addition reaction

bromination (halogenation)

name the addition reaction

bromo(halo)hydrin formation

name the addition reaction

oxymercuration

name the addition reaction

hydroboration

name the addition reaction

diol formation (oxidation)

name the addition reaction

hydrogenation (reduction)

BDE equation

change of H= BDE of reaction - BDE of product

Markovnikov’s Rule

in addition to HX, H2O, ROH to alkene, the H adds to the carbon (of the double bond) with the greater number of hydrogen

how to find the most substituted carbon?

the carbon that is connected to the most substituents (tertiary is greater than primary)

how to find the most stable carbocation?

the most substituted carbon is most stable

carbonation

the molecule’s ability to have rearrangement

IUPAC (E)

molecule that has substituents on opposite sides of the double bond

the stronger the acid…

the weaker the conjugate base

IUPAC (Z)

molecule that has substituents on the same side of the double bond

how to find the major product

the product that follows Markovnikov’s rule is the major product

higher pKa means…

more stable molecule

racemic mixture

enantiomer (one dash, one wedge)

hydrohalogenation

HX

Acid-Catalyzed

H2O, H2SO4

Halogenation

X2

Halohydrin formation

X2, H2O

oxymercuation (reduction)

1. Hg(OH)2, H2O

2. NaBH4

Hydroboration (oxidation)

1. BH3

2. H2O2m NaOH

Syn Dihydroxylation

1. OsO4

2. NaHSO3, H2O

or

1. OsO4

2. tBuOOH

Catalytic Reduction

H2, Pd/C

Ozonolysis

1. Os

2. (CH3)2S