Quiz 2 Flashcards
What are the reagents used for a grignard reaction and how is it formed
RMgBr; formed by combining RBr and Mg using ether
What are the reagents for an organolithium reaction and how is it formed
RLi and LiBr; formed with RBR via Li and ether
What are the reagents for a Gilman reaction and how are they formed
R2CuLi; formed with RLi and CuI via ether
What happens when water reacts with organometallics
The grignard will react in an acid-base reaction to make a conjugate acid of the grignard and a hydroxide ion of the reagent
What is the mechanism for an epoxide ring opening via grignard reagents
R attacks less substituted C onto O creating RO- connected to MgBr. C closest to MgBr attacks H onto Cl creating ROH
What is the mechanism for an epoxide iring opening via gilman reagents
R2CuLi attacks least substituted carbon onto O. O attacks H onto Cl creating R-CH(OH)CH2CH=CH2
What is the outcome and reagents of a Simmons-Smith reaction with alkenes (ring with double bond on the right and double bond O on the top)
CH2I2 is added to the group which is reacted via Zn(Cu) and ether; this created a ring that is cyclicly bonded to CH2 with O double bonded to the top and its enantiomer along with ZnI2
How do you name an aldehyde and what is it
Carbonyl group bonded to hydrogen and carbon; add “-al” in place “-e”
How do you name a ketone and what is it
Carbonyl group bonded to two carbons; add “one” in place of “e”
What is the mechanism for a nucleophilic acyl addition
O of carbonyl attacks H creating an alcohol which through resonance makes the Carbon positive by moving double bond to O. Nucleophile attacks carbon to add it to the molecule
What does formaldehyde and a C-Nuc form
Primary alcohol
What does an aldehyde and a C-Nuc form
A secondary alcohol
What does an ketone and a C-Nuc form
tertiary alcohol
What is the mechanism for adding an organolithium compound to a carbonyl group
Li attacks C onto O making covalent bond between O and Li. O attacks H of H3O turning it into an alcohol
What is an acetylide anion
CH triple bonded to C covalently bonded to Na
What is the mechanism fro adding acetylide anions to a carbonyl group
covalent bond attacks C onto O adding it to the attacked carbon and forming a covalent bond between O and Na. O attacks H of H3O turning into an alcohol
What is the mechanism for adding cyanide to a carbonyl group
C lone pair attacks C onto O. O attacks H of another cyanide onto the C making a cyanohydrin
What is the mechanism for the formation of a wittig reagent
Ph3P attack CH3I onto I which covalently bonds to Ph3P. Butylithium attacks H of CH3 onto Carbon forming butane, a phosphonium ylide, and LiI
What is the mechanism of a Wittig reaction
Phosphonium ylide attacks c onto O forming betaine. Proximity of O and Ph3P with their charges creates a bond betweent them. Bonds between O and C and Ph3P and CH2 are broken to go to existing bonds. This creates Triphenylphosphine oxide and an alkene
What does the addition of water to a carbonyl make
Hydrate (C bonded to two hydroxyls)
What is the mechanism for adding an alcohol to a carbonyl group
O attacks acid/base forming an alcohol. Nucleophile attacks C onto O adding itself to the molecule. CB attacks H of newly added hydroxyl onto O. Other OH attacks H which is then protonated. This creates a resonance structure where O can donate one of its lone pairs to make neutral carbon. EtOH attacks C adding itseld to the molecule. CB attacks newly added H onto O forming an acetal
What is the mechanism for using acetal as a protecting group of a carbonyl
O of carbonyl attack H forming an alcohol. OH of acetal attacks C onto O attacking it to the C. CB attacks H onto O directly attached to C. Opposite OH attacks H forming a hemiacetal. Protonation happens. OH of acetal attacks C. CB attacks H onto O forming a cyclic acetal
What is the mechanism for the addition of ammonia to a carbonyl group
NH3 attacks C onto O. O attacks H of N onto N. O attacks H of NH4 onto N. O attacks H of another NH4 onto N. Water protonates itself. NH3 attacks H onto N forming imine CR2=NH
What is the mechanism for adding NaBH3 to a carbonyl group
H attacks C onto O. O attacks H forming alcohol
