Carbonyls (Ch 13-16) Flashcards
Aldehydes undergo Nucleophilic _______ reactions.
Addition
Ketones undergo Nucleophilic ______ reactions.
Addition
Carbonyl Compounds with LGs undergo Nucleophilic ________ Reactions
Substitution
A Nucleophilic Substitution Reaction is composed of which 2 types of reactions?
Addition then Elimination
Which is more reactive: Aldehydes or Ketones?
Why?
Aldehydes
Because aldehydes are less crowded and less stable than ketones.
Two Main Steps of Nucleophilic Addition
- Nucleophilic Attack of the carbonyl carbon
- Protonation of the -O to form -OH
Nucleophilic Addition of Aldehydes and Ketones forms _____.
Alcohols
What are the 2 Steps of Nucleophilic Substitution Mechanism?
- Nucleophilic Attack of the Carbonyl C
(Moved the Double Bond e- onto the O) - the pi bond is reformed and Z comes off as a LG
Which Carboxylic Acid has the best LG?
Acid Chlorides
Carboxylic Acid Derivative with Worst LG
Amides
Which 2 compounds have LG of similar Basicity?
Esters
Carboxylic Acids
2 Ways to ID Oxidation Reaction
Increase in # of C-Z bonds
Decrease in # of C-H bonds
2 ways to ID reduction rxns
Decrease in # of C-Z bonds
Increase in # of C-H bonds
Why are Carbolxylic Acid Derivatives Called Carboxylic Acid Derivatives?
A hydrolysis rxn results in a carboxylic acid
2-ethylpentanal is what type of molecule?
aldehyde
-al suffix
C1 is the CHO carbon
When naming an ester, which side is the alkyl group and which side is the acetyl group?
The chain connected directly to the O is the alkyl.
The chain with the carbonyl carbon is the acyl group.
How to Name an Ester
1) Name the Alkyl Group
2) Name the Acyl Group
3) Suffix -oate
Alcohol + Carboxylic Acic –>
Ester
What type of molecule is propyl 3-methylbutanoate?
Ester
-OCH3
methoxy group
What type of molecule is 3-methoxy-N-methylbutanamide?
Amide
Namingng an Amide
Specify which C or N substituents are attached to. C1 is the Carbonyl Carbon.
Suffix -amide
2, 2-dimethylcyclopentanone is what type of molecule?
Ketone
suffix -one designates a _____
Ketone
-al designates a _______
Aldehyde
-oate designates a ____.
Ester
-oic acid designates a _____.
Carboxylic Acid
-oyl chloride designates a ______.
Acid Chloride
Designates an Aldehyde
-al
Designates and Ester
-oate
Designates a Carboxylic Acid
-oic acid
Designates an Acid Chloride
-oyl chloride
Designates a Ketone
-one
Acetal
2 Ethers on the Same Carbon
(2 -OR groups on same carbon)
Hemiacetal
An Alcohol and an Ether Group attached to the same Carbon
(-OH and -OR group on same carbon)
Hemiketal AKA
Hemiacetal
Ketal AKA
Acetal
NaBH4
acid or base
strong or weak
weak base
LiAlH4
acid or base
strong or weak
strong base
alkene –> alkane
reducing reagent
H2/Pt
Ketone –> Alcohol
reducing reagent
H2/Pd-C
H2/Pd-C will reduce a _____ before ______.
H2/Pd-C will reduce an alkene to alkane before reducing =O (ketone) to -OH (alcohol)
2 Reagents that can be used to reduce Aldehydes to Alcohols
NaBH4
LiAlH4
Reagent used to Reduce Ketones to Alcohols
NaBH4
Reagent used to Reduce Acid Chloride to Alcohol
LiAlH4
*Notes: Goes through a aldehyde intermediate
Reagent used to
Reduce Acid
Chloride to Aldehyde
LiAl-tritertbutoxy
Reagent used to Reduce Ester to Alcohol
LiAlH4
Reagent used to Reduce Ester to Aldehyde
DIBAL-H
