SP21 234 R10 Organometallics Key PDF

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics 1. Perform a retrosynthetic analysis on the following molecule (work backwards) from the given commercially available starting material.

CHO O Br

1.

8.

5.

2.

6.

3.

7.

4.

Br

1

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics 2. For the following transition metal complex, assign the total number of valence electrons and the oxidation state of the metal.

Cl

Total Number of Electrons:

Cl

Oxidation State of Zr:

Zr

CO OC

Total Number of Electrons:

CO Cr

CO

OC

Oxidation State of Cr:

CO

Total Number of Electrons:

Cl Ir N

Ph3P

Oxidation State of Ir:

Ph

H

Total Number of Electrons:

Rh Ph3P

Cl

Oxidation State of Rh:

Total Number of Electrons: Fe Oxidation State of Fe:

2

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics 3. Predict the product for the following transformation.

Me

benzene

Me

(1 mol %) H2 CH2Cl2

Me

Br

(Ph3P)4Pd (1 mol %)

O O

CF3

1

MeO

2. Mg(0), THF 3. Pd(PPh3)4 (1 mol %) CF3

3

Br

Ph

, THF

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics

1. Br2, FeBr3

CF3

2.

)4 (1 mol %)

(HO

CF3

OH 3. PCC, CH2Cl2

1. P

4

H)2

NO2

F

Ph

Br

2. NaBH4, MeOH

O

4

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics 4. Provide the necessary reagents to accomplish the desired organic reactions. Please number the steps and note that some reactions will require more than one step.

O e

2

CF3

t

Br NH2

5

CO

t

CF

Ph NH2

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics

Me Me Me

Me

MeO

Me Me B(OH)2

O O

6

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics 5. Provide a retrosynthesis for the following transformations.

Me SiMe3

Br Me

OTf 1. 4. 2.

3.

7

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CHEM 234 • Organic Chemistry II Review 10 • Organometallics CF3

Me

O Me

NO2 1.

4.

2.

3.

8

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