U3-3-2 - Haloalkanes Flashcards by Miss Peciulyte | Brainscape

Q

What is this type of molecule called?

A

Haloalkane

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Q

What feature of haloalkanes allows nucleophiles to attack them?

A

Carbon-halogen bond is polar.

(Nucleophile can attack C)

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Q

A

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Q

Why is this type of reaction significant in chemistry?

A

Increases length of carbon chain

(which is normally hard to do!)

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Q

A

This is shorthand for acid hydrolysis

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Q

Name this type of reaction

A

Acid (catalysed) hydrolysis

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Q

A

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Q

Carbocation

A

A species with a positively charged carbon atom.

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Q

Which type of carbocations are the least stable?

A

Primary

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Q

Why are tertiary carbocations the most stable?

A

Due to the inductive effect.

Alkyl groups push e⁻ density towards the positively charged C atom, which stabilises the charge.

(steric hindrance is a 2nd reason)

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Q

What do the numbers refer to in S_N1 and S_N2?

A

Number of particles in RDS

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Q

Step 1 of S_N1

A

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Q

Step 1 of S_N1 - draw in curly arrow(s)

A

Q

S_N1 step 2 - draw in curly arrow(s)

A

Q

Which step is the slow (RDS) step in S_N1?

Step 1 - Carbocation formation

Step 2 - Substitution

A

Step 1 - Carbocation formation

Q

S_N2 - draw in curly arrow(s)

A

Q

S_N2

A

Q

What is missing in this transition state?

A

Must have square brackets and negative charge!

Q

Which mechanism forms an inverted product:

S_N1 or S_N2?

i.e. inverted stereochemistry at chiral centre

A

S_N2

(Attacking group is always opposite to where the leaving group was.)

Q

Which mechanism forms a racemic mixture:

S_N1 or S_N2?

A

S_N1

(Attacking group can attach to either side of carbocation.)

Q

When is S_N1 preferred over S_N2?

A

When a stable carbocation (tertiary) is formed

(or in case of steric hindrance)

Q

When is S_N2 preferred over S_N1?

A

When a less stable carbocation (primary) is formed