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Organic Chemistry: Synthesizing Compounds

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Please answer the following questions. Draw the synthesizing of the compounds.

1. Starting with toluene, prepare 2-bromo-4-nitrotoluene.
2. Starting with toluene, prepare 2,4,6-trinitrobenzoic acid.
3. Starting from benzene, prepare p=chlorostyrene.
4. p-Bromotoluene reacts with potassium amide to give a mixture of m- and p- methyl aniline. Explain how these products are produced by showing the mechanism involved. (draw).

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This solution provides detailed drawings of synthesizing compounds.

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Organic Chemistry Synthesis Reactions and Stereochemistry

Please see the attached file for the complete problems.

1. Predict the product of the reaction below. Be sure to indicate stereochemistry when appropriate.

2. Provide proper IUPAC names for each compound below.

3. The compound below has been isolated from the safflower plant. Consider its structure to
answer the following questions.

4. What is the molecular formula for this natural product?

5. What is the degree of unsaturation for this compound?

6. Assign E or Z configuration to each of the double bonds in the compound.

7. Consider an unknown with the molecular formula C4H6. How many degrees of unsaturation are present?

8. Select the best reagent or sequence of reagents from the list provided which would best
accomplish each transformation below. Place the letter corresponding to the reagent(s) in the
blank to the left of each reaction. Each transformation requires only one answer.
a) H2SO4, H2O, HgSO4
b) H2, Lindlar
c) 1. BH3, THF
2. H2O2
d) 1. NaNH2, NH3
2. CH3CH2I
e) 1. Br2, CCl4
2. 2 NaNH2, NH3
f) 1. HCl
2. NaNH2, NH3
g) Li/NH3
h) 1. NaNH2, NH3
2. CH3CH2CH2I

9. The intermediate in the first step of this reaction sequence is called a

a. carbocation
b. cyclonium ion
c. mercurinium ion
d. mercapto species.

10. In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label "Compound A: ." Compound A reacts with 1 mol equiv of hydrogen and, after treatment with acidic , gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled "Compound B (isomer of A)." Compound B also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone after treatment with acidic .

How many degrees of Unsaturation does compound A possess?

Suggest structures for A and B.

What was the other product formed in the KmnO4 oxidation of B?

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