DESERT - Substitution Thinking Q's

Adventures on

Notebook

A desert island

Notes about the island

Use it with caution

Backpack

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

Tiririri-ri!

Introduction

Answer the following substitution questions to escape from the island!

Backpack

Missions

Boat

Click on each section to proceed!

Shrubbery

Plane

Shelter tent

Forest

Backpack

Mission

Plane

Solvent

See how solvent impacts the reaction

Suitcases

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?

mmm

A. Increases

B. Decreases

C. Stays the same

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?

Let's go!

A. Increase

B. Decrease

C. Stays the same

Backpack

Woow!!

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

Backpack

Missions

Boat

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Shrubbery

Plane

Shelter tent

Forest

Backpack

Mission

Forest

Electrophile

We will explore how electrophiles impact which reaction occurs

Logs

Backpack

Electrophiles for substitution reactions

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

Backpack

Which electrophile would be better for an SN1 reaction?

B.

A.

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Backpack

Which electrophile would be better for an SN2 reaction?

B.

A.

Backpack

Awesome!!

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

Backpack

Missions

Boat

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Shrubbery

Plane

Shelter tent

Forest

Backpack

Mission

Shrubbery

Leaving Group

Better leaving groups lead to faster reactions!

Food

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!!

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

Backpack

Missions

Boat

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Shrubbery

Plane

Shelter tent

Forest

Backpack

Mission

Fabrics

Nucleophile

Let's see how nucleophiles impact reaction rate

Shelter tent

Backpack

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

A. Increase

B. Decrease

C. Stay the same

Backpack

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

A. Increase

B. Decrease

C. Stays the same

Backpack

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

A. Increase

B. Decrease

C. Stays the same

Backpack

Oh yeah!!

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

Backpack

Missions

Boat

Almost there!

Shrubbery

Plane

Shelter tent

Forest

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

Keep searching

Keep searching

Code: 1234

Keep searching

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

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.

Forest

Mountains

Plane

Shrubbery

Shelter tent

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.

Congratulations!

Wow, you got it!

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

Play again!

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

Keep trying!

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

Ouch!

Better nucleophiles have more electron density and are less hindered!

Keep trying!

Think about the nucleophile structure!

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.
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