kami hull ochem II mechanisms

What happens during an Acid chloride hydrolysis reaction?

the Cl gets replaced with OH

What’s the mechanism for an Acid chloride hydrolysis reaction?

1. H₂O (nucleophile) attacks carbonyl carbon (electrophile) of the acid chloride

2. pi bond goes to Oxygen and forms a tetrahedral intermediate

3. since oxygen wants 2 bonds to be neutral, the negative ex-carbonyl Oxygen uses its new lone pair to form the double bond again

4. this kicks off the Cl

5. the added water still has a positive Oxygen, so another H₂O molecule (or lowk u can use pyridine) is added to grab a proton (H+) to remove the positive charge

6. you’re left with a neutral -OH group, making a carboxylic acid!

~ Minor Products Formed: H₃O+ and Cl-

What happens during an Acid-catalyzed ester hydrolysis reaction?

the -OR group gets replaced with -OH and also creates a HOR’ byproduct

(aka ester + acid (typically H₃O+) & heat = carboxylic acid)

What’s the mechanism for an Acid-catalyzed ester hydrolysis reaction?

1. the carbonyl Oxygen gets protonated using the H₃O⁺

2. now that Oxygen is positive, so you can use water as a (weak) nucleophile!

3. that water attacks the carbonyl carbon, forcing the pi bond up to the O⁺

4. uhhhh

What happens during a Base-promoted ester hydrolysis (Saponification) reaction?

What’s the mechanism for a Base-promoted ester hydrolysis (Saponification) reaction?

1. poop

2. pee

3. doodooooo

What happens during an Acid-promoted amide hydrolysis reaction?

What’s the mechanism for an Acid-promoted amide hydrolysis reaction?

1. ?

2. ??

3. ???

What happens during a Base-promoted amide hydrolysis reaction?

What’s the mechanism for a Base-promoted amide hydrolysis reaction?

1. ?

2. ??

3. ???

What happens during an Acid-promoted nitrile hydrolysis reaction?

What’s the mechanism for an Acid-promoted nitrile hydrolysis reaction?

What happens during a Base-promoted nitrile hydrolysis reaction?

What’s the mechanism for a Base-promoted nitrile hydrolysis reaction?

What happens during an Acid chloride + amine reaction?

What’s the mechanism for an Acid chloride + amine reaction?

1. ?

2. ??

3. ???

What happens during an Ester + Grignard reagent reaction?

What’s the mechanism for an Ester + Grignard reagent reaction?

1. ?

2. ??

3. ???

What happens during an Ester reduction with Lithium Aluminum Hydride?

What’s the mechanism for an Ester reduction with Lithium Aluminum Hydride?

What happens during an Amide reduction with Lithium Aluminum Hydride?

What’s the mechanism for an Amide reduction with Lithium Aluminum Hydride?

What happens during Base-catalyzed Aldol Condensation reactions?

What’s the mechanism for Base-catalyzed Aldol Condensation reactions?

What happens during the Acidic Dehydration of an aldol product?

What’s the mechanism for the Acidic Dehydration of an aldol product?

What happens during Claisen Condensation reactions?

What’s the mechanism for Claisen Condensation reactions?

What happens during DIBAL-H reductions?

What’s the mechanism for DIBAL-H reductions?

Explain Selective cross-aldol reactions

Michael additions/selectivity and 1,2- vs. 1,4-addition

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Review acetoacetic ester synthesis and alkylation

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Dieckmann mechanisms

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What happens during Fisher Esterification reactions?

What’s the mechanism for Fisher Esterification reactions?