What happens when representations fail to represent

What happens when representations fail to represent? Graduate students’ mental models of organic chemistry diagrams Amanda M. Strickland, Adam Kraft and Gautam Bhattacharyya Supplementary data Task 3 A. Br

Ag+

+

Br

Br N CH 3

N CH 3

Ag Br

Ag+

Br

Br

Br+ Br

H

N N CH 3 CH 3

Br

N CH 3

B. NBS THF/H2O (3:1) 0 oC HO

O

O

N Br

HO

O

OH

O

O

O

Br

OH

O

HO

OH

O+

Br

-H+

O

O

O

-H+

OH

O+

OH

O O O

C. NHBoc

O

HN

HCOOH

O HN

OH O

HN

O

O

HN

O

O

HCOO-

-H+

NH2

NH2 H2 N HO

+OH

O

H 2O +

O

HN +

HN

HN

O

H2O H

O-

OH

D. OH

OMe

BBr 3

Me

Br2 B

O+

OMe

Br -

Br2B O

OH

H 2O

BBr 3

From Work-up

-

-Br

E. Me O

Base CO2H

O

H

H

O

O

O

O-

B: Me

Me

CO2H

CO2H H

F. OTBS

OTBS HO

O

O

O O

r.t.

NTs

O

O

SnCl4, CH2Cl2

O

O NTs

O

OTBS

OTBS Cl

SnCl3

O

O

Cl3Sn +

O

O O

O

O NTs

O

O NTs

O

OTBS Cl3Sn

Cl-

Cl3Sn

O

O

O

H

O

O

OTBS

O

+H2O

O

O NTs

O NTs

O OTBS HO

O

O

O

O NTs

G.

OH

1.) MsCl/Et3N 2.) Heat H

OH

O

H OH OH

MsCl

O OMs

 -H+ H

O

H. HO

OH

Ag+

HO

OH

O

O

HO

Ag

OH

H

+

O+

OH

Ag Ag

-Ag+ -H+

O

OH

Repeat

O

O