Chem 250 Writing Assignment Lab 4 – Personal Care Product 10/10/14 one page summary of primary article due 10/24/14 annotated bibliography due 11/14/14 final project due

Q: How do you detect chirality ? A: Polarimetry ! Chem Act 12A Model 3 Q: How do you detect chirality ? A: Polarimetry ! Chem Act 12A Model 3

2 Stereogenic Centers and a plane of symmetry

Chemistry 250-02 Organic Chemistry I Fall, 2014 Day 13 10/1/14 Chemistry 250-02 Organic Chemistry I Fall, 2014 Day 13 10/1/14 Chapter 6 An Overview of Organic Reactions What Kind of Reactions Are There? Why do Reactions Happen? How do Reactions Happen? What Factors Control Reactions?

Functional Groups

Functional Groups & Polarity

Functional Groups C-FG or R-FG

Reaction Mechanisms Answer the question in detail: How do we get from reactants to products? Include all steps in a multistep reaction Indicate bond-making and bond-breaking by using curved reaction arrows Follow the electron flow so arrow becomes a new 2 electron bond ( - ) or a lone pair ( : ) Electrophile Nucleophile

How Are Bonds Broken and Made ? homolytic heterolytic Elec Nuc

Some Types of Organic Reactions

Some Types of Organic Reactions Addition Elimination Substitution hydrolysis - reaction with H2O condensation - formation of H2O Rearrangement

Garoutte ChemAct 33 p. 133-134

Garoutte ChemAct 33 p. 133-134 Oxidation Reduction Substitution Hydrolysis Elimination (reverse is Addition) Acid-Base Oxidation - 3 types Add Oxygen Lose Hydrogen Loss of Electrons Substitution Condensation Addition (reverse is Elimination)

How do we classify these reactions How do we classify these reactions? Addition, Elimination, Substitution, Rearrangement

How do we classify these reactions How do we classify these reactions? Addition, Elimination, Substitution, Rearrangement Substitution Nucleophilic Polar-Ionic H+ Elimination Addition Δ Substitution Radical hν

Reaction Types

What Kinds of Organic Reactions Are There What Kinds of Organic Reactions Are There ? How Can We Describe These Reactions ? Problem 6.1

What Kinds of Organic Reactions Are There What Kinds of Organic Reactions Are There ? How Can We Describe These Reactions ? Problem 6.1 elimination addition substitution rearrangement

What Kinds of Reactions Are These?

Polar Reactions Recall polarity These reactions involve a nucleophile (e- - rich) and an electrophile (e- - poor) What kind of reaction is this ?

Nucleophiles attack Electrophiles

Reaction Types

What kind of reaction is the transformation shown below? an elimination reaction a rearrangement reaction a substitution reaction an addition reaction none of these

In the reaction shown below which is the electrophile ? propene the H of HCl the Cl of HCl propane none of these all of these

In the reaction shown below which is the nucleophile ? propene the H of HCl the Cl of HCl propane none of these all of these

Free Energy Diagrams What Does the TS (‡) Look Like ?

Which statement best describes the energetics of the reaction shown below? C2H4 + H2 → C2H6 exothermic with positive activation energy exothermic with negative activation energy endothermic with positive activation energy endothermic with negative activation energy cannot be determined without knowing BDE’s

On the reaction energy profile shown below which species has the highest energy ? II III IV V

On the reaction energy profile shown below which is the highest energy intermediate? II III IV V

On the reaction energy profile shown below which represents the slowest step? I to II II to III III to IV IV to V All steps proceed at the same rate

On the reaction energy profile shown below which represents the energy of the reaction? The energy difference between: I and II I and III II and III III and IV III and V I and V

Organic Rxns and Biological Rxns

Which of the following represents a correctly drawn reaction mechanism?

Electrophilic Addition to Alkenes

Electrophilic Addition to Alkenes

Problems 5.6 and 5.7

Where are the electrophilic sites? Where are the nucleophilic sites?

Follow the arrows to the products

Two Reactions of Radicals R-H → R-H →

Radical Substitution The Mechanism

Radical Addition in Prostaglandin Synthesis

Polar Bonds and Polar Reactivity

Some Nucleophiles and Electrophiles

Nucleophiles and Electrophiles React !

C-H bond breaking in alkanes

How Can Bonds Be Broken and Made ?

Polar Reactions

Nucleophiles and Electrophiles

Problem 5.4 and 5.8