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SP 2006 Final Examination Organic II 200pts (Weighted As 300)

This document is an organic chemistry exam covering various topics including: 1) Identifying functional groups in molecules 2) Drawing Lewis structures of different classes of compounds 3) Determining which molecule has the lowest pH 4) Naming organic reactions 5) Defining common organic chemistry terms 6) Questions involving resonance structures, aromaticity, reaction mechanisms, and more. The exam contains 17 questions testing knowledge of functional groups, organic reactions, naming conventions, and more. It provides 200 points for the main exam questions and allows up to 4 bonus points for identifying Dr. Roche's influential mentors.

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Ummi Khairani Urfa
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57 views

SP 2006 Final Examination Organic II 200pts (Weighted As 300)

This document is an organic chemistry exam covering various topics including: 1) Identifying functional groups in molecules 2) Drawing Lewis structures of different classes of compounds 3) Determining which molecule has the lowest pH 4) Naming organic reactions 5) Defining common organic chemistry terms 6) Questions involving resonance structures, aromaticity, reaction mechanisms, and more. The exam contains 17 questions testing knowledge of functional groups, organic reactions, naming conventions, and more. It provides 200 points for the main exam questions and allows up to 4 bonus points for identifying Dr. Roche's influential mentors.

Uploaded by

Ummi Khairani Urfa
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Sp 2006 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).
R C NH2 O R O H R O O R O

R C H O

R C R O

R C Cl O

R C O-R O

2) Draw Lewis structures (lone pairs not required) for the following classes of compound. (12pts)

Ether

Carboxylic Acid

Peroxy Acid

Cyclopropane

Isocyanate

Xanthate

Alkyl Azide

Aryl Diazonium Ion

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)

(a) NH2 O (b) R OH R R' (c) R O C R R C C O OR R' R O (d)

(e) Br Mg-Br

(f)

N2 +

Br

O (g) R NH2 H O (h) C C H R NH2 O

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5) Define the following terms (15pts). PROTECTING GROUP

AROMATICITY

PERICYCLIC REACTION

KINETIC PRODUCT

CONJUGATED DOUBLE BONDS

6) Give one use of Molecular Orbital theory, and also state a disadvantage of MO theory. (4pts).

7) Draw all the resonance structures for the below species (dont need curly arrows) (6pts).
H N +

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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)
CH3 P N Mg-Br H H N+

O O +

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)
O O H 1) HOCH2CH2CH2OH; H3O+ 2) NaBH4 3) H3O+ Excess HI Ph O O heat H CF3

NO2 CH3Cl, AlCl3

NO2 1) Zn, HCl 2) NaNO2, HCl 3) CuCl, HCl

Br2, uv light

Br

OH

1) NaOH 2) CH3OCH2CH2-Br

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

OH OH (in exactly a 1:1 ratio)

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)


NO2

Br O 2N CO2H

CO2H

CHO

O H

O OH

NO2

Cl O O Ph-N H O H

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


H N O Ph O NH H N NH2 CCl3 NH2 CN

F3C

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


(a) CH3 CO2H CH3CH2-O-H CH3CH2-O-O-H

(b)

CH3OH

NH3

CH4

F (c) O

F CO2H Cl Cl O Cl CO2H Cl O CO2H

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 4 points) During the last week of class, Dr. Roche showed photographs of his two most influential mentors. One was from England, and the other from the US. Name those two mentors, and name the universities at which Dr. Roche was fortunate enough to learn from these world experts.

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