Quiz 4 Orgo II Lab

Zaitzev’s rule

Zaitzev’s rule

an elimination reaction the major product is the more stable alkene with the more highly substituted double bond

Markovnikov’s rule

When HZ is added to unsymmetrical alkene, the hydrogen will add to the carbon with the most number of hydrogens

E1 mechanism

E2 mechanism

Evelyn effect

the product composition changes during the course of the reaction

Its hypothesized that the reason is because of the starting mixture of cis- and trans- isomers

What equipment is used in fractional distillation?

Vigreux column

SN1 reactions

-Unimolecular

-polar protic solvents

-carbocation

-tertiary and secondary halides

-AgNO3 in ethanol

SN2 reactions

-Bimolecular

- polar aprotic solvents

-primary and secondary halides

-NaI in acetone

why wont bromobenzene be reactive?

the molecule wants to keep its aromaticity

IR Single Bonds

appear below 1500 cm-1

IR Double bonds

appear between 1600-1850 cm-1

IR Triple Bonds

appear between 2100-2300 cm-1

X-H (O-H, N-H, C-H) bonds

appear between 2700-4000 cm-1

Carboxylic acid IR

Alkene

• note the peaks between 1600-1850

• to conform a C=C-H bond, there should be a small peak at 3100

Alkyne

• note peaks around 2100-2300

• C(triple)C-H will have peak at 3300

Alcohol

Board band around 3200-3600

Primary Amine

two short peaks after 3000

Secondary Amine

one peak after 3000

Conjugation ==

lower wavenumber

example: 1750 to 1680

Effect of Resonance

Resonance decreases the wavenumber

Woodward Fieser rules: base line

217 nm

Woodward Fieser rules: each extra double bond

add 30 for each

Woodward Fieser rules: auxochromic alkyl group

add 5 for each

Woodward Fieser rules: each exocyclic double bond

add 5 for each

(An exocyclic double bone is when one vinylic position is part of a ring and the other vinylic position is not part of the ring)

Woodward Fieser rules: homoannular diene

add 39

Which of the following is the least soluble in water?

A. Alcohols

B. Secondary Amines

C. Primary Amines

D. Carboxylic acids

B. Secondary Amines

Dehydration of cyclohexanol follows:

A. Markovnikov’s Rule

B. Zaitsev’s Rule

C. Evelyn Effect

D. Hallalov Rule

B. Zaitsev’s Rule

In the dehydration mechanism, the first step is:

A. Formation of the carbocation

B. Protonation of the “OH” group

C. Loss of a proton

D. Rearrangement

Protonation of the “OH” group

Dehydration reaction is done in a distillation apparatus:

A. The alkene is toxic

B. To push the equilibrium to the right

C. To push the equilibrium to the left

D. To condense the reactants back

B. To push the equilibrium to the right

Draw the product of the dehydration reaction of