PART 2 - Resonance 1. Construct a reaction diagram including 2-methylpenta-1,3-diene and H- Br as the reactants. Include all lone pairs of electrons. 2. Identify the nucleophile and the electrophile in the drawing above. 3. Draw a double headed arrow beginning at the nucleophilic pi electrons of the double bond in the 3 position of 2-methylpenta-1,3-diene and ending on the electrophilic hydrogen. Make sure to push the electrons in the bond between the H and Br onto the Br, with a double headed arrow, so that the octet rule (actually the duet rule for H) is obeyed. 4. Draw all of the possible intermediate(s) that can result from this attack. Try to draw these with the correct bond angles and shapes. 5. Identify the one that is most stable by circling it. 6. Using a double headed arrow show the nucleophilic electrons on Br attacking the most stable intermediate drawn above. 7. Draw the product(s) that is/are formed. Include any stereochemistry involved. 8. Name the product(s). 9. Repeat the steps above using the nucleophilic pi electrons of the double bond in the 1 position of 2-methylpenta-1,3-diene.

PART 2 - Resonance 1. Construct a reaction diagram including 2-methylpenta-1,3-diene and H- Br as the reactants. Include all lone pairs of electrons. 2. Identify the nucleophile and the electrophile in the drawing above. 3. Draw a double headed arrow beginning at the nucleophilic pi electrons of the double bond in the 3 position of 2-methylpenta-1,3-diene and ending on the electrophilic hydrogen. Make sure to push the electrons in the bond between the H and Br onto the Br, with a double headed arrow, so that the octet rule (actually the duet rule for H) is obeyed. 4. Draw all of the possible intermediate(s) that can result from this attack. Try to draw these with the correct bond angles and shapes. 5. Identify the one that is most stable by circling it. 6. Using a double headed arrow show the nucleophilic electrons on Br attacking the most stable intermediate drawn above. 7. Draw the product(s) that is/are formed. Include any stereochemistry involved. 8. Name the product(s). 9. Repeat the steps above using the nucleophilic pi electrons of the double bond in the 1 position of 2-methylpenta-1,3-diene.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter15: Radical Reactions

Section: Chapter Questions

Problem 13E

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Consider this nucleophilic substitution reaction. 1. Highlight the electrophilic carbon in red, and highlight the leaving group in blue. Highlight the atom in the nucleophile that will attack the electrophilic center in green. Only atoms need to be highlighted and not the lone pairs or formal charges. 2. Draw the product(s) of the reaction. Include all lone pairs.
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8,9,10
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11
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