DESERT - Substitution Thinking Q's

Use it with caution

Notes about the island

Notebook

Adventures on

A desert island

Backpack

Tiririri-ri!

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

Answer the following substitution questions to escape from the island!

Introduction

Click on each section to proceed!

Missions

Shelter tent

Boat

Forest

Shrubbery

Plane

Backpack

Backpack

Mission

Suitcases

Plane

See how solvent impacts the reaction

Solvent

Backpack

mmm

C. Stays the same

B. Decreases

A. Increases

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

Backpack

Let's go!

C. Stays the same

B. Decrease

A. Increase

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

Backpack

Woow!!

You've got food and cooking tools

Yeah!

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

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Missions

Backpack

Shelter tent

Boat

Forest

Shrubbery

Plane

Backpack

Mission

We will explore how electrophiles impact which reaction occurs

Electrophile

Forest

Logs

Backpack

Primary only do SN2 Resonance stabilized primary and secondary do SN1 or SN2 Tertiary only can do SN1

Electrophiles for substitution reactions

Backpack

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B.

Which electrophile would be better for an SN1 reaction?

A.

Which electrophile would be better for an SN2 reaction?

Backpack

B.

A.

Backpack

Awesome!!

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

Yeah!

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

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Missions

Shelter tent

Boat

Forest

Shrubbery

Plane

Backpack

Mission

Better leaving groups lead to faster reactions!

Leaving Group

Shrubbery

Food

Backpack

Backpack

Here we go!!

Which leaving group would lead to a faster reaction?

Backpack

Almost there!!

Which leaving group would lead to a faster reaction?

Backpack

keep it up!!

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

Yeah!

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

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Missions

Shelter tent

Boat

Forest

Shrubbery

Plane

Backpack

Mission

Let's see how nucleophiles impact reaction rate

Nucleophile

Fabrics

Shelter tent

Backpack

Backpack

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

C. Stay the same

B. Decrease

A. Increase

Backpack

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

C. Stays the same

B. Decrease

A. Increase

Backpack

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

C. Stays the same

B. Decrease

A. Increase

Backpack

Oh yeah!!

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

Yeah!

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

Almost there!

Missions

Shelter tent

Boat

Forest

Shrubbery

Plane

Backpack

Keep searching

Keep searching

Keep searching

Code: 1234

Keep searching

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.

Wait, take a look in your backpack

Enter the complete code you have obtained to access the last mission

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.

Find your Backpack!

Shrubbery

Shelter tent

Mountains

Plane

Forest

Desert island map

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

Wow, you got it!

Play again!

Congratulations!

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

Ouch!

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

Keep trying!

Ouch!

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

Keep trying!

Ouch!

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

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

Keep trying!

Ouch!

Better nucleophiles have more electron density and are less hindered!

Think about the nucleophile structure!

Keep trying!

Clue

Primary only do SN2 Resonance stabilized primary and secondary do SN1 or SN2 Tertiary only can do SN1

Mission

Determine how solvents impact reaction rate

SN2 reactions prefer aprotic solvents - makes nucleophiles more nucleophilic SN1 reactions prefer protic solvents - stabilize the carbocation intermediate

Clue

Primary only do SN2 Resonance stabilized primary and secondary do SN1 or SN2 Tertiary only can do SN1

Clue

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

Clue

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

Clue

Acetone is an aprotic solvent Methanol is a protic solvent

Mission

Determining reaction rate based on solvent

SN2 reactions prefer aprotic solvents - makes nucleophiles more nucleophilic SN1 reactions prefer protic solvents - stabilize the carbocation intermediate

Clue

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

Clue

Acetone is an aprotic solvent Methanol is a protic solvent

Clue

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

Mission

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• Consectetur adipiscing elit.
• Sed do eiusmod tempor incididunt ut.