DESERT - Substitution Thinking Q's

A desert island

Adventures on

Notebook

Notes about the island

Use it with caution

Introduction

Answer the following substitution questions to escape from the island!

Think about the different factors that impact substitution reactions as you answer these questions!

Tiririri-ri!

Backpack

Backpack

Plane

Shrubbery

Forest

Boat

Shelter tent

Missions

Click on each section to proceed!

Solvent

See how solvent impacts the reaction

1

Plane

Suitcases

Mission

Backpack

You are running a SN1 reaction in acetone as the solvent, what happens to the reaction rate if you change the solvent to methanol?

A. Increases

B. Decreases

C. Stays the same

mmm

Backpack

You are running a SN2 reaction in acetone as the solvent, what happens to the reaction rate if you change the solvent to methanol?

A. Increase

B. Decrease

C. Stays the same

Let's go!

Backpack

They will be added to your backpack.You will need them to be able to eat during the days you spend on the desert island

Yeah!

You've got food and cooking tools

Woow!!

Backpack

Plane

Shrubbery

Forest

Boat

Shelter tent

Backpack

Missions

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Logs

Forest

Electrophile

We will explore how electrophiles impact which reaction occurs

2

Mission

Backpack

Electrophiles for substitution reactions

Primary only do SN2Resonance stabilized primary and secondary do SN1 or SN2Tertiary only can do SN1

Backpack

A.

Which electrophile would be better for an SN1 reaction?

B.

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Backpack

A.

B.

Backpack

Which electrophile would be better for an SN2 reaction?

They will be added to your backpack.You will need them during the days you spend on the desert island

Yeah!

You've got a rope, maybe it will be useful

Awesome!!

Backpack

Backpack

Plane

Shrubbery

Forest

Boat

Shelter tent

Missions

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Backpack

Food

Shrubbery

Leaving Group

Better leaving groups lead to faster reactions!

3

Mission

Which leaving group would lead to a faster reaction?

Here we go!!

Backpack

Which leaving group would lead to a faster reaction?

Almost there!!

Backpack

They will be added to your backpack.You will need them during the days you spend on the desert island

Yeah!

You've got an axe, maybe it will be useful

keep it up!!

Backpack

Backpack

Plane

Shrubbery

Forest

Boat

Shelter tent

Missions

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Backpack

Shelter tent

Fabrics

Nucleophile

Let's see how nucleophiles impact reaction rate

4

Mission

A. Increase

B. Decrease

C. Stay the same

Would the reaction rate increase, decrease, or stay the same if we switched the nucleophile from water to NaOH?

Backpack

A. Increase

B. Decrease

C. Stays the same

Would the reaction rate increase, decrease, or stay the same if we switched the nucleophile from NaOCH3 to CH3OH?

Backpack

A. Increase

B. Decrease

C. Stays the same

Would the reaction rate increase, decrease, or stay the same if we switched the nucleophile from NaOCH3 to KOtBu?

Backpack

They will be added to your backpack.You will need them during the days you spend on the desert island

Yeah!

You've got a lantern, maybe it will be useful

Oh yeah!!

Backpack

Backpack

Plane

Shrubbery

Forest

Boat

Shelter tent

Missions

Almost there!

Wait, take a look in your backpack

Check items in your backpack and use the flashlight to look for the code to access the last mission that will allow you to leave the desert island.

Keep searching

Code:1234

Keep searching

Keep searching

Keep searching

1st code: 1

2nd code: 2

3rd code: 3

Boat

Planks

Build a raft!

Take all the tools you've learned to answer predict the product and thinking questions!

5

Mission

Forest

Plane

Mountains

Shelter tent

Shrubbery

Find your Backpack!

You have already traveled the whole island, you have managed to build a raft, but now you do not remember where you left your backpack and you will need it before you can leave here. On the map you can see the places where your backpack could be.

Drag the parts of the map to find where you have left your backpack and be able to flee from the desert island.

Desert island map

Great job on identifying how different trends impact the different reactions that we've learned about

Congratulations!

Play again!

Wow, you got it!

Keep trying!

Think about what protic or aprotic solvents do for the reaction!

Ouch!

Keep trying!

Think about the structure and determine if it is primary, secondary or tertiary

Ouch!

Keep trying!

Use pKas to help you - negative pKas indicate that the leaving group is a good one!

Leaving groups that are more stable in the conjugate base form lead to faster reaction rates

Ouch!

Keep trying!

Think about the nucleophile structure!

Better nucleophiles have more electron density and are less hindered!

Ouch!

Primary only do SN2Resonance stabilized primary and secondary do SN1 or SN2Tertiary only can do SN1

Clue

SN2 reactions prefer aprotic solvents - makes nucleophiles more nucleophilicSN1 reactions prefer protic solvents - stabilize the carbocation intermediate

Determine how solvents impact reaction rate

Mission

Primary only do SN2Resonance stabilized primary and secondary do SN1 or SN2Tertiary only can do SN1

Clue

Nucleophiles impact SN2 reaction ratesrate = k[elec][nuc]Nucleophiles don't impact SN1 reaction ratesrate = k[elec]

Clue

Nucleophiles impact SN2 reaction ratesrate = k[elec][nuc]Nucleophiles don't impact SN1 reaction ratesrate = k[elec]

Clue

Acetone is an aprotic solventMethanol is a protic solvent

Clue

SN2 reactions prefer aprotic solvents - makes nucleophiles more nucleophilicSN1 reactions prefer protic solvents - stabilize the carbocation intermediate

Determining reaction rate based on solvent

Mission

Nucleophiles impact SN2 reaction ratesrate = k[elec][nuc]Nucleophiles don't impact SN1 reaction ratesrate = k[elec]

Clue

Acetone is an aprotic solventMethanol is a protic solvent

Clue

Better leaving groups are more stable when removed from the moleculeThings that make conjugate bases stable also make leaving groups stable

Clue

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Clue

Better leaving groups are more stable when removed from the moleculeThings that make conjugate bases stable also make leaving groups stable

Clue

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• Sed do eiusmod tempor incididunt ut.

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Mission