3. Perform the following tasks for each reaction. i. Identify the functional group (FG) in the starting material with the most accurate name: alcohol, aldehyde, epoxide, ester, ether, or halohydrin. ii. Label the reagent over the arrow as a good nucleophile; a strong base; and/or a strong acid. (A reagent can have more than one label.) Draw the major organic product. (Hint: Remember to keep track of stereochemistry over the course of the reaction if given. It may be helpful to redraw the starting material in the conformation needed to close epoxide ring.) iii. i. Starting Material OH ii. Reagent iii. Product a. NaOH FG = b. Excess HBr FG = с. 1. Li(CH2);CH3 2. H3O" (Acidic workup for neutralizing charge) FG = d. ОН NaH FG = е. HBr FG =

3. Perform the following tasks for each reaction. i. Identify the functional group (FG) in the starting material with the most accurate name: alcohol, aldehyde, epoxide, ester, ether, or halohydrin. ii. Label the reagent over the arrow as a good nucleophile; a strong base; and/or a strong acid. (A reagent can have more than one label.) Draw the major organic product. (Hint: Remember to keep track of stereochemistry over the course of the reaction if given. It may be helpful to redraw the starting material in the conformation needed to close epoxide ring.) iii. i. Starting Material OH ii. Reagent iii. Product a. NaOH FG = b. Excess HBr FG = с. 1. Li(CH2);CH3 2. H3O" (Acidic workup for neutralizing charge) FG = d. ОН NaH FG = е. HBr FG =

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 13E

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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…