Sp 2007 Final Examination Organic II

200pts (Weighted as 300)

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

Aryl Diazonium Ion

Cyclobutane

3) Circle the molecule in question (2) with the lowest pH (3pts).

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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

(c) N 2+ O (d) R NH2 R NH2 Br

(e) Br R' O (f) R C R R C C R R' Mg-Br

(g) NH2 O (h)

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5) Define the following terms (15pts). CONDENSATION REACTION

AROMATICITY

KINETIC CONTROL

THERMODYNAMIC PRODUCT

CONJUGATED DOUBLE BONDS

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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11) Design a synthetic scheme for the below transformation (5pts)

CH2CH3

Cl

12) Write the mechanism for the electrophilic aromatic substitution reaction below. (8pts)
NO2 NO2
+

HSO4

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13) Provide reagents to accomplish five of the following transformations. (15pts)

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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14) Circle the most basic nitrogen in each molecule. (9pts)

NH CN NH2 N H 2N NH2 Cl3C H N O Br O H N CF3

15) Circle the strongest acid in the following threesomes. (9pts)

(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

16) Name the following compounds in IUPAC form (14pts).

O H3C Br F3C

O O

CH3 CH3 O HO O NH2

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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)

1) excess CH3-Br 2) Ag2O, H2O, heat

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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