Synthesis
Convert a primary alcohol into a grignard reagent
PBr3 followed by Mg2+
Draw the reaction including LiALH4
Hydride attacks the carbonyl carbon forming a C-H bond
Reagent that oxidizes a primary alcohol to a carboxylic acid
Chromic Acid
Which compound is most reactive toward nucleophilic acyl substitution?
A. Amide
B. Ester
C. Acid chloride
D. Carboxylate
C: Cl- is the best leaving group
This bond results from side-on orbital overlap.
pi bond
Starting from cyclohexene, synthesize trans-1,2-dibromocyclohexane
Add Br2/CCl4 to cyclohexene
Draw the mechanism of an organocuprate reaction
draw
Reagent that oxidizes secondary alcohol to ketone
PCC OR Chromic acid
What is the product when an acid chloride reacts with methanol (CH₃OH)?
A. Ketone
B. Ester
C. Amide
D. Carboxylic acid
B- ester
These reagents add OH in a Markovnikov fashion without rearrangements.
Hg(OAc)₂, H₂O; then NaBH₄
Starting from a secondary alcohol, synthesize a tertiary alcohol with one additional carbon, without over-oxidation at any step
Oxidation to a ketone, Grignard addition, acidic work up
Draw the mechanism of a Wittig reaction
square intermediate
This reagent takes an ester to an alcohol
LiAlH4
Amides are less reactive toward nucleophilic substitution because:
A. Nitrogen is electronegative
B. Resonance stabilizes the C–N bond
C. The carbonyl is less polarized
D. Amides are sterically hindered
B- the lone pair on N delocalizes into the carbonyl
These reagents add OH anti-Markovnikov with syn addition
BH₃·THF; then H₂O₂, OH⁻
Convert a ketone into an alkene, then convert that alkene into an alcohol at the less substituted carbon
Wittig reaction followed by hydroboration-oxidation
Draw the mechanism of an epoxide reacting in basic vs. acidic conditions
Acidic: favor attack of more substituted carbon (OH on less)
Basic: favor attack of less substituted (OH on more)
Reaction that converts ketones to esters and aldehydes to carboxylic acids
Baeyer-Villiger Reaction
Draw mechanism of ketone reacting for extra points
A molecule contains both an ester and a ketone. It is treated with 1 equivalent of CH₃MgBr followed by aqueous workup.
What is the most likely outcome?
A. Both carbonyls react once
B. Only the ester reacts
C. Only the ketone reacts
D. The ester reacts twice
C- just one equivalent
Products of imine hydrolysis
Carbonyl compound and an amine
Synthesize this Product
On slides
Acid catalyzed mechanism of primary amine condensing with ketohyde to form imine
In the first stage of the mechanism, acid-catalyzed nucleophilic addition yields a carbinolamine intermediate. In the second stage of the mechanism, acid-catalyzed beta-elimination yields the imine and a molecule of water via an iminium ion intermediate
Rank the following compounds by reactivity to reduction: ester, alcohol, ketone, aldehyde, carboxylic acid.
Aldehyde, ketone, ester, carboxylic acid, alcohol
In nucleophilic acyl substitution, the rate-determining step is typically:
A. Nucleophile attack on carbonyl
B. Formation of tetrahedral intermediate
C. Collapse of tetrahedral intermediate
D. Proton transfer
B- formation of the tetrahedral intermediate usually has the highest energy barrier
Predict this Product
On slides