Worksheet 4b

Question 1

What do these reagents do?

Answer 1

Brominates the allylic position

DO NOT CLEAVE THE CARBON

Question 2

What does this reagent do?

Answer 2

Elimination.

LG leaves and double bond adds in the most stable position.

Question 3

What do these reagents do?

Answer 3

Jone’s reagent

When benzylic hydrogen is present, ALL of them will be oxidized into carboxylic acid.

Question 4

Why is this NR?

Answer 4

There are no benzylic hydrogens to oxidize.

Question 5

How can I give a molecule a LG?

Answer 5

NBS, hv

Question 6

How can I substitute a LG with OH?

Answer 6

NaOH

Question 7

What is this structure called?

How do I add it to an R group

Answer 7

Aldehyde

You can add it to an R group using PCC as a reagent

Question 8

How many steps are in this synthesis?

What are the steps + reagent?

Answer 8

2 steps

1: Elimination, add a double bond using NaOEt
2: Hydroboration/Oxidation, at OH to the end.

Use 1. BH₃, THF 2. H₂O₂, NaOH, H₂O

Question 9

How many steps are in this synthesis?

What are the steps + reagent?

Answer 9

3 Steps

1: Give the allylic position a good LG using NBS, hv
2: Hydrate the allylic position with NaOH
3: Oxidize the allylic position with PCC

Question 10

What is the difference between anti-aromatic and non-aromatic?

Answer 10

Anti-aromatic means it satisfied rules 1-3 but pi electrons = 4N

Non-aromatic can mean non-cyclic, SP3 hybridization, non-planar,.