What prefix do methanoic acid and methanal share?
- Methanoic acid = formic acid
- Methanal = formaldehyde
Two carbon unit with one carbon in carbonyl
Equation for specific rotation
- c = concentration
- l = path length (in decimeters!)
Larger substituents are more stable as axial or equatorial?
Maximum number of stereoisomers a compound can have?
Effect of Sn2 on stereochemistry
Inversion - Must attack backside
Rate of Sn2 is dependent on ______
Both substrate and nucleophile
Oxidizing primary alcohols (using _____) leads to _____
Oxidizing secondary alcohols => ______
1˙ OH + PCC => aldehyde
- Stronger oxidizing agent => COOH
2˙ OH => ketone
Aldehydes can be oxidized => _____
Aldehyde => COOH
Aldehydes, ketones, and carboxylic acids can be reduced to ______ using ______
Reduced to OH using LiAlH4
Amides can be reduced to amines using _____
Esters can be reduced to _______ using ______
Esters + LiAlH4 => pair of OH
Effect of protic solvents
Protonate nucleophile or H bond => inhibit nucleophilicity
Effect of CrO3 or potassium dichromate on primary OH?
Oxidize it all the way to COOH
Can you use nonpolar solvents in nucleophile-electrophile reactions?
No b/c reactants are polar
Rank carboxylic acid derivatives from most reactive to least
Anhydride > COOH + Esters > Amides - Derivatives of higher reactivity can form derivatives of lower reactivity (but not vice versa) - Anhydride can form ester but ester cannot form anhdyride
What make good LGs?
Weak bases Conjugate bases of strong acids Resonance/induction - Weak bases are more stable in solution
Alkyl (carbon) groups are EDG or EWG?
C = EDG
Why are aldehydes more reactive than ketones?
Less steric hindrance
Function of acetals/ketals
2 OH + carbonyl - C with 2 OR, R, and an H
Phenol + oxidizing agent => _____
Quinone (ketones instead of OH) - Does not have to have aromatic ring
Convert acetal back to ______ and _____ using ______
Carbonyl and two OHs using catalytic acid
OH are made into better LG/protected using _____
Mesylates (-SO3CH3) and tosylates (SO3C6H4CH3) - Protection is removed using strong acid
Jones oxidation components - What does it do?
CrO3, dilute sulfuric acid, acetone - Oxidizes 1˙ OH to COOH and 2˙ OH to ketone
Oxidation of quinones => ______
React one OH w/ carbonyl => _____
HCN + carbonyl => ______
- C attached to OH, R, R, and C triple bonded to N
Imines tautomerize to form ______
How are geminal diols formed?
Hydration reaction (H2O attacks carbonyl)
KMnO4 (potassium permanganate) is a strong _____
Carbonyl carbanion/oxanion that lost H bond (has 3 bonds and one LP)
- Can perform resonance
- Formed due to base deprotonating alpha carbon from carbonyl compound => carbanion => protonated to form enol
Carbanion attacks another carbonyl compound w/ a double bond
- Attacks double bond
Both aldehyde and OH
- Aldehyde/ketone enolate (due to deprotonation from base) attacks keto form
- Usually gets dehydrated (lose OH) in strong base and high temperature
Retro-aldol reaction = catalyzed by ______
Heat and base
LDA (lithium diisopropylamide)
High temperatures and weak base favor which enolate (thermodynamic/kinetic)?
Thermodynamic - Proceeds slowly b/c of weak base => kinetic enolate has time to interconvert to thermodynamic
Most basic ketone (H3C - C=O - CH3)