ROM Exam 4

Part of Unit 5 and all of Unit 6

Jones Oxidation on primary alcohol

Jones Oxidation on secondary alcohol

Jones oxidation is

Acidic, and full strong oxidation

KMnO4 oxidation is

basic conditions, full oxidation

Pyridinium chlorochromate (PCC) is

mild oxidation

KMnO4 oxidation with primary alcohol

PCC oxidation of primary alcohol

Why are carbonyls so reactive?

Due to it being sp2 carbon, flat, trigonal planar. It is very polar, and the partial positive charge on the carbon makes it very electrophilic.

Why is an aldehyde more reactive than a ketone?

Fewer sterics around the carbon. Less induction, so the partial positive charge is less stable

Reagents used to reduce carbonyls

NaBH4 or LiAlH4

What can generate carbon nucleophiles?

Organothium, Grignard, and Wittig pathway (the ylide)

Why are Grignard and organolithium so useful?

Creates carbon-carbon bonds

This is the same as…

(carbon nucleophile)

Are carbanions stronger or weaker nucleophiles than anionic oxygen nucleophiles?

More nucleophilic. Carbon is less electronegative, so it is less able to hold a negative charge

Strong oxygen nucleophiles

Are charged

weak oxygen nucleophiles

Are uncharged/neutral

What are acetals used for in synthesis

Used as protecting groups

what reaction does this represent?

Carbonyl reduction reaction

-none

ketone

-ol

alcohol

-al

aldehyde

whats the product?

What's the product?

whats the product

whats the product

whats the product

whats the product?

whats the product