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Name If you object to your graded final being placed in a box outside my office then check here 1) Identify the class of compounds that the following molecules belong to (12pts).
O R C O-R O R C H O R C R O R C Cl
O R O O R O R C NH2 R O H
2) Draw Lewis structures (lone pairs not required) for the following classes of compound. (12pts).
Carboxylic Acid
Peroxy Acid
Ether
Isocyanate
Aldehyde Hydrate
Alkyl Azide
Cyclobutane
4) The following reactions are named after their inventors - give the names of the following reactions (16pts)
H O (a) C C H O (b) R OH R
O OR
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AROMATICITY
KINETIC CONTROL
THERMODYNAMIC PRODUCT
6) Give one use of Molecular Orbital theory, and draw a species whose bonding is not accurately described by a Lewis structure. (4pts).
7) Draw all the resonance structures for the below species (dont need curly arrows) (6pts).
+ Br CH3 H
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8) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (15pts)
H H N+ N
O +
CH3 N O OH
9) Pick one of the above aromatic molecules, and use the polygon rule to demonstrate its aromaticity. (8pts)
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10) Give the products in six of the following reactions, paying attention to regio/stereochemistry where applicable. (18pts)
heat H NO2 1) Zn, HCl 2) NaNO2, HCl 3) CuCl, HCl NO2 CH3Cl, AlCl3 NO2 H 1) HOCH2CH2CH2OH; H3O+ 2) NaBH4 3) H3O+ CF3
O O
Br2, uv light
Excess HI Ph O O
Br
OH
1) NaOH 2) CH3OCH2CH2-Br
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Cl
12) Write the mechanism for the electrophilic aromatic substitution reaction below. (8pts)
NO2 NO2
+
HSO4
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CO2H O H
CHO O OH
NO2
Br NO2 Br
Br
Br
O 2N CO2H
O O Ph-N H
O H
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(a)
CH3CH2-O-O-H
CH3 CO2H
CH3CH2-O-H
(b)
CH3OH
NH3
CH4
F (c) O
F O OH Cl Cl O Cl
O OH Cl
F O Cl Cl
O H3C Br F3C
O O
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17) Fill in the blanks for two of the following reactions. (6pts)
(a)
O H H Ph
NH2 Ph
Ph
H2SO4, CH3OH
(b)
O
(c)
H H Ph
Ph
NaOCH3, CH3OH
18) When one equivalent of hydrogen chloride is added to the following conjugated diene, a mixture of two products is formed.
H-Cl
i) Draw the two products. ii) Provide the step-by-step mechanism which explains the generation of both products. iii) One of the products contains a chiral center. Asterix (*) that chiral carbon. (9pts)
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19) Give the mechanism for two of the below conversions. (16pts)
CH3OH, NaOH (a) O O HO O NH2 NaNO2, HCl + N N ClO-CH3
(b)
(c) H3C
O Ph
HOCH2CH2OH H2SO4
O H3C
O Ph
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*Bonus question* (up to 2 points) Name two countries that share borders with ENGLAND.
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