Organic Chemistry Exam #1

pKa values, functional groups, branched alkanes

C_sp³-H pKa

55-60

C_sp²-H pKa

45

R₂N-H pKa

35

C_sp-H pKa

25

HO-H pKa

15.7

RO-H pKa

16

R₃N⁺-H pKa

10

RCOOH pKa

5

HCl pKa

-4

H₂SO₄ pKa

-5

alcohol

ROH

ether

ROR’

carboxylic acid

RCOOH

ester

RCOOR’

ketone

aldehyde

alkylhalide/haloalkane

RX (X=halogen)

amide

amine

RNR’R’’

alkene

C=C

alkyne

the more stable the base, the _______reactive

less

lower pKa indicates __________ acid

stronger

constitutional isomers

same formula and different connectivity of atoms

F (halogen branch name)

fluoro

Cl (halogen branch name)

chloro

Br (halogen branch name)

bromo

I (halogen branch name)

iodo

Hydrocarbons have _____(IMF)

london dispersion forces

Alcohols have ______(IMF)

hydrogen bonds, london dispersion forces, dipole-dipole

Alkylhalides have _____(IMF)

dipole dipole and london dispersion forces

larger halogen has __________ boiling point

higher

meth-

1

eth-

2

prop-

3

but-

4

pent-

5

hex-

6

hept-

7

oct-

8

non-

9

dec-

10

formal charge=

VE-bonds-lone e^-

With resonance, the negative charge is most stabilized when it is on the ____ electronegative atom

most

Do NOT exceed the octet on period ___ elements

2

2 effective electron pairs: EG? hybridization?

linear, sp

3 effective electron pairs: EG? hybridization?

trigonal planar, sp²

4 effective electron pairs: EG? hybridization?

tetrahedral, sp³

Bronsted-Lowry acid

any species that can donate a proton

Bronsted-Lowry base

any species that can accept a proton

conjugate acid

acid that results from protonation of a base

conjugate base

base that results from loss of a proton from an acid

Conjugate base of a strong acid must be a ____ base

weak

A more stable conjugate base=_______acid

stronger

a more electronegative element (inc from left→right on periodic table) gives a _______ acid

stronger

As you go down a column in the periodic table, the size increases which corresponds to a __________ acid

stronger

energy of gauche 60deg methyl-methyl interaction

3.8kJ/mol

energy of methyl eclipsing a methyl

11 kj/mol

energy of a methyl eclipsing a H

6 kj/mol

The most important resonance contributers have the greatest number of ___________

filled octets

The resonance structure with ________ formal charge is more important

fewer

When the pH of the environment is ____ than the pKa of the compound, the environment is considered acidic and the compound will exist predominately in its protonated form

less

Resonance structures with equally good Lewis structures are _______ and contribute ______ to hybrid

equivalent, equally

decalin

two fused rings

Where are arrows drawn with an acid base reaction?

One is drawn from the base and attacking the proton, the second arrow is drawn from the bond and going to the atom connected to the bond

cis 1,2 pattern

axial, equatorial

trans 1,2 pattern

axial, axial or equatorial, equatorial

cis 1,3 pattern

axial axial or equatorial equatorial

1,3 trans pattern

axial equatorial

1,4 cis pattern

axial equatorial

1,4 trans pattern

axial axial or equatorial equatorial