1. CHM247 Tutorial #4 http://assiduous-atom.tripod.com/ (slides can be accessed here)

2. Question 1 “Predict the major organic product(s) of benzyl magnesium bromide reacting with each of the following compounds, followed by addition of H 3 O +” a)pentanal b)CO 2 c)2-butanol d)propanone (acetone)  followed by H 3 O + and heat

3. Question 1 “Predict the major organic product(s) of benzyl magnesium bromide reacting with each of the following compounds, followed by addition of H 3 O +” a)pentanal b)CO 2 c)2-butanol d)propanone (acetone)  followed by H 3 O + and heat

4. Question 1 “Predict the major organic product(s) of benzyl magnesium bromide reacting with each of the following compounds, followed by addition of H 3 O +” a)pentanal b)CO 2 c)2-butanol d)propanone (acetone)  followed by H 3 O + and heat

5. Question 2 “Perform a retrosynthetic analysis followed by a proposed synthesis of the following molecule. The starting materials available to you are toluene (methylbenzene) and acetylene” Look for where the starting materials are going to end up in the product

6. Question 2 Making C-C bonds:  Carbon Nucleophile + Carbon Electrophile  C-C bond Carbon Nucleophiles: Grignard reagents, acetylide anions, enolate anions, cyanide anions Carbon Electrophiles: Aldehydes, ketones, alkyl halides possible approaches:

7. Question 2

8. Question 3 “An intermediate Y in the synthesis of cerulein, an important antibiotic, was prepared in the following manner. Fill in structural formulas for the missing compounds X, Y, and Z. (PCC is a reagent discussed in CHM138/151” Reduces alkynes to trans alkenes Oxidizes 1 o alcohols to aldehydes and 2 o alcohols to ketones Evidence for a carbonyl Reduces alkynes/alkenes to alkanes

9. Question 3