Organic exam answer

Final Exam Ian R. Gould

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H He

Li Be B C N O F Ne

Na Mg Al Si P S Cl Ar

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr

Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe

Cs Ba Lu Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn

CHEM 234, Spring 2008

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H/H ~1.0

Eclipsing

H/Me ~1.4

Me/Me ~2.6

Me/Me ~0.9

Et/Me ~0.95

i-Pr/Me ~1.1

t-Bu/Me ~2.7

Gauche

Me/Et ~2.9

Interaction Energies, kcal/mol

ASU ID or Posting ID

Person on your RIGHT (or Aisle)

1__________/18 .......................9__________/72.........................

2__________/14.........................10__________/22.........................

3__________/10.........................11__________/20.........................

4__________/12.........................12__________/40.........................

5__________/12 .......................13__________/25.........................

6__________/12........................14__________/50.........................

7__________/20........................15__________/40.........................

8__________/18........................

Extra Credit_____/5 Total (incl Extra)________/385+5

C NR2

RC CRR2C CR2

Aromatic

CR OH

O

C X

R NH2R OH

amine

alcohol

3Y > 2Y > 1Y

020406080100120140160180200220

H2C X

H2C NR2

OCH2

01234567891011

C CHC H

O

CR OH

O

Aromatic Ar H

Alkylmainly 8 - 6.5C CH2

C CH3

O

3Y > 2Y > 1YAlkylOCH2

C

O

(!, ppm)

variable and condition dependent, ca. 2 - 6 !

R C N

O H C N

C

N

C

CH

C ON H

C H

C N

O

HC

OC

H

C CH

COR

O

N H

C H

C

OO H

C O H

O

CNR2

O

30003100

28502960

3300

broad ~3300

broad with spikes ~3300

2200

broad ~30001710

2200

1650

272028202 peaks

1735

16001660

1680

range of values

broad peak

small range usuallystrong

1600

C

H

C

H

C C

HH

C

H

C

H

C

H

C

H

H

H

H

H

Approximate Coupling

Constants, J (Hz), for 1H NMR Spectra

~7

~10

~2

~15

~2

~8

Infrared Correlation Chart

NMR Correlation Charts

3000 200025003500 1500(cm-1)

nomen

acidity 1

acidity 2

basicity

reactivity

basicity 2

malonics

Stork

reactions

synthons

pericyclic

mxns 1

mxns 2

synth 1

synth 2

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CHM 234, Spring 2008, FINAL EXAM - 2 - NAME

Question 1 (18 pts.) Provide IUPAC names for the following structures, do not forget to use E/Z and R/S as appropriate.

O

O

A

the anion in A is destabilized by the O of the ester, which acts as a resonance donating group to the enolate anion, the oxygen in B acts as a weak inductive withdrawing group to the enolate

(2S),5-dimethyloct-(5E)-enoic acid

O

O

ethyl propanoate

a)

b)

CO2H

O

O

B

O

C

H H H