organic exam answer
DESCRIPTION
final exam answer.TRANSCRIPT
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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
PRINTED LAST NAME
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