Organic Synthesis and Qualitative Analysis

What 3 things are required to know in order to determine a multi-step synthesis?

1. chemistry of functional groups

2. how to choose reagents that will accomplish functional group interconversion (proper regiochemistry and/or stereochemistry

3. How to use protecting groups to prevent function groups from undergoing a reaction while another functional group is being transformed

NaNH₂ is a good reagent for what process?

Deprotonation

Which reagent reduces an alkyne to an alkane?

Pd or Pt

Which reagent reduces an alkyne to an alkene?

Deactivated/poisoned catalysts (Lindlar)

what happens to an aldehyde when reacted with alcohol in acidic solvent?

Acetal production

What happens to an acetal in hot aqueous acid?

Reverts to original carbonyl

Acetal groups are resistant to oxidation by

alkaline oxidizers

Identify the mechanism

Grignard reaction with esters

Identify the mechanism

alcoxymercuration-demercuration of alkenes

How does a ketone react with NH₃ and H₂, Pt?

creates imine, reduces to amine faster than reduction to alcohol

identify the mechanism

Gabriel amine synthesis

identify the mechanism

acyl chloride to amide

what makes tertiary alkyl halide undergo eliminations rather than Sn2 with nucleophiles?

steric hindrance to backside attack

Identify the mechanism

Hoffman rearrangement

What does enolate alkylation do?

Replaces an alpha hydrogen with an alkyl group (forms new C-C)

Identify the mechanism

Malonic ester synthesis

Identify the mechanism

Acetoacetic ester synthesis

What does H₂ and Pt do to a NO₂ group?

reduces to primary amine

Identify the mechanism

Sandmeyer replacementWha

What are the key reagents so a Sandmeyer replacement?

NO₂ ion (bound to H or metal), and acidic cold solvent

What reagents can reduce an alkyne to an enol or ketone?

H₂O and H₂SO₄ in HgSO₄

What solvent is needed to form a gignard reagent

ether