CHEM 302 - Dr. Hartel
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CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 2
1. Nomenclature Give the proper systematic name for each of the following structures on the lines. Cl
NO2 CH2CH2CH3 Br NO2
Br OH F 1,2-dibromo3-nitrobenzene 4-chloro-3-propylphenol 2-cyclopropyl-4-fluoro-1-nitrobenzene
2. Concepts Label each of the following compounds as AROMATIC, NONAROMATIC or ANTIAROMATIC on the lines provided.
S O NH N O N Aromatic Aromatic Aromatic Aromatic Aromatic
HN NH N N
N H non-Aromatic non-Aromatic non-Aromatic Aromatic non-Aromatic
3. Reactions
1 CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 2
Draw the major product or products of each of reaction in the boxes provided. If multiple organic products are equally likely, show each. For stereoselective reactions, be certain that your structures clearly indicate stereochemistry.
CH2CH3 CH2CH3 Cl2, FeCl3
Cl
NH2 Br NH2 NaNH 2 + NH3 (liq) NO NO2 2 NO2
CH3 CH3 NaNO2, HCl 0 oC NH2 N2 Cl
Br OCH3 - CH3O
NO2 NO2
HO CN HO CN HNO3, H2SO4
NO2
2 CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 2
CO2H Na2Cr2O7
H2SO4, H2O
- H2NNH2, HO O
Br Br Br2, FeBr3
Br
2-butanol, H2SO4
OH
OH phenyldiazonium chloride N N
3 CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 2
Br Br CuCN
N N CN Cl
O O OH HNO , H SO O2N 3 2 4 OH
Br
H2SO4, Heat HO3S Br
Zn(Hg), HCl
O
O O O O 1) , AlCl Cl 3 O 2) H O 2 O
4. Mechanisms Draw a complete arrow pushing mechanism for the following reaction. Include all resonance forms for your intermediates.
4 CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 2 a. CH3 O CH3 CH3 CH3 O O O
O
S O H
O O S O O S O O S O
O O O
H H H
CH3 CH3 O O
Base H O S O O S O
O O
H H
b.
O O O O H N N N O O O HO HO
F F F
O O O N N N O O HO O HO F HO F F 5. Synthesis Propose a selective multi-step synthesis of each target molecule starting with the compound provided. Show the necessary reagents and products for each step.
5 CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 2 a. O
OH
O2N NO2
CH CH3 3 HNO , H SO CH3Br, AcCl3 3 2 4 (x2) O2N NO2 O
OH Na2Cr2O7 H2SO4, H2O O2N NO2
b. CN
Br
Br NH2 NaNO , HCl Br2, FeBr3 NaNH2 2 0 oC NH3 (liq)
N CN N CN CuCN Br2, FeBr3 Cl
Br
6. Application of Concepts a. The following hydrocarbon is actually a polar compound. Why is it polar, and which direction is the dipole oriented? Thoroughly explain your rationale (structures will be helpful).
6 CHEM 302 - Dr. Hartel Winthrop University Self Evaluation 2
When other resonance structures are drawn, one can see that there is a major contribution from the contributor in green. In this drawing, both rings are now aromatic, meaning this is a MAJOR contributor to the structure overall. Thus the left side is partially negative and the right side partially positive.
b. Rank the following hydrocarbons in order of increasing acidity (1 most acidic to 3 least acidic). Thoroughly explain your rationale (structures will be helpful).
Removal of the most acidic proton from each hydrocarbon gives the conjugate bases below. The leftmost structure is aromatic and thus very stable, meaning the conjugate acid is rather strong. The rightmost structure is antiaromatic and thus very unstable, meaning the conjugate acid is rather weak. The center structure is unaffected by resonance, and thus its conjugate acid strength lies somewhere in between.
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