DISCUSSION 4 ORGANIC 2 RESPONSE

Your Name:

1. Determine if each compound below is aromatic, anti-aromatic, or neither (only one option per structure). Then, discuss why you believe this option to be true for each case.

(a)

(b)

Komero, Rosecinna

"cyclic

b)

n0 - anti-ar omatic

7te

(assume planar)

aromatic cules

C ant-aromatic

" conu9ation ol the way aroun d ring (NO Sps)

pi-e: 2, l6, lo, 14,18... planar

planar

pie- (re) =4

make it anti -aromatic

cyclic conyugation v 8 pi e X

fotlouw most rules So its anti-oromatic

(c)

(d) H

non arom att C

(Neither)

ONot cy clic = not aromatc

- Nerther

aromatic

dcycic/ eonyugation lil ley

Planar �

aromatie

2. (a) Starting from benzene. propose a viable synthesis for the para-product below. For cach step. show all nccessary rcagents/conditions and draw the major product expected after cach step in your proposed synthesis.

steps

Aicls

mayor product

para-product (major)

HCI

(b) Discuss why minimal ortho product is observed in this synthesis.

This has to do with steric crowding steric h indrance effect.

Or interaet

CH 3 CI

Aic's

or rather tne

This effect the shape Cconfor mation) and how the molecules act.Cbond uwith each other)

(c) Show how you could modify your synthetic proposal so that the ortho product formed below is the only product observed. You can fill in the missing reagents in the correct step order above or below the arrow. (Hint: Sulfonation is a reversible reaction).

Cons

HgC

AlCl3

A

HSO3

cH3

(o signals

Al Cl3

(d) Discuss how 'H NMR would allow a synthetic chemist to differentiate between the ortho and para products shown above. Be specific. Your discussions should talk about number of signals expected, splitting patterns, integrations and important chemical shift regions that would be significant in differentiating these two constitutional isomers.

para e aromati

A Singlet 2 B Doublet 3eDoublet 4o Dovblet

5E Muliplet

Hc

HS03

o F Doublet

A Doublet

E Doblet

ortho-product (only product observed)

trplet H Triplet

Olute H2 SO4

0ttho

8 signa's

Your Name:

1. Determine if each compound below is aromatic, anti-aromatic, or neither (only one option per structure). Then, discuss why you believe this option to be true for each case.

(a)

(b)

Komero, Rosecinna

"cyclic

b)

n0 - anti-ar omatic

7te

(assume planar)

aromatic cules

C ant-aromatic

" conu9ation ol the way aroun d ring (NO Sps)

pi-e: 2, l6, lo, 14,18... planar

planar

pie- (re) =4

make it anti -aromatic

cyclic conyugation v 8 pi e X

fotlouw most rules So its anti-oromatic

(c)

(d) H

non arom att C

(Neither)

ONot cy clic = not aromatc

- Nerther

aromatic

dcycic/ eonyugation lil ley

Planar �

aromatie

2. (a) Starting from benzene. propose a viable synthesis for the para-product below. For cach step. show all nccessary rcagents/conditions and draw the major product expected after cach step in your proposed synthesis.

steps

Aicls

mayor product

para-product (major)

HCI

(b) Discuss why minimal ortho product is observed in this synthesis.

This has to do with steric crowding steric h indrance effect.

Or interaet

CH 3 CI

Aic's

or rather tne

This effect the shape Cconfor mation) and how the molecules act.Cbond uwith each other)

(c) Show how you could modify your synthetic proposal so that the ortho product formed below is the only product observed. You can fill in the missing reagents in the correct step order above or below the arrow. (Hint: Sulfonation is a reversible reaction).

Cons

HgC

AlCl3

A

HSO3

cH3

(o signals

Al Cl3

(d) Discuss how 'H NMR would allow a synthetic chemist to differentiate between the ortho and para products shown above. Be specific. Your discussions should talk about number of signals expected, splitting patterns, integrations and important chemical shift regions that would be significant in differentiating these two constitutional isomers.

para e aromati

A Singlet 2 B Doublet 3eDoublet 4o Dovblet

5E Muliplet

Hc

HS03

o F Doublet

A Doublet

E Doblet

ortho-product (only product observed)

trplet H Triplet

Olute H2 SO4

0ttho

8 signa's