Quiz 2

Question 1

What are the reagents used for a grignard reaction and how is it formed

Answer 1

RMgBr; formed by combining RBr and Mg using ether

Question 2

What are the reagents for an organolithium reaction and how is it formed

Answer 2

RLi and LiBr; formed with RBR via Li and ether

Question 3

What are the reagents for a Gilman reaction and how are they formed

Answer 3

R2CuLi; formed with RLi and CuI via ether

Question 4

What happens when water reacts with organometallics

Answer 4

The grignard will react in an acid-base reaction to make a conjugate acid of the grignard and a hydroxide ion of the reagent

Question 5

What is the mechanism for an epoxide ring opening via grignard reagents

Answer 5

R attacks less substituted C onto O creating RO- connected to MgBr. C closest to MgBr attacks H onto Cl creating ROH

Question 6

What is the mechanism for an epoxide iring opening via gilman reagents

Answer 6

R2CuLi attacks least substituted carbon onto O. O attacks H onto Cl creating R-CH(OH)CH2CH=CH2

Question 7

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)

Answer 7

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

Question 8

How do you name an aldehyde and what is it

Answer 8

Carbonyl group bonded to hydrogen and carbon; add “-al” in place “-e”

Question 9

How do you name a ketone and what is it

Answer 9

Carbonyl group bonded to two carbons; add “one” in place of “e”

Question 10

What is the mechanism for a nucleophilic acyl addition

Answer 10

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

Question 11

What does formaldehyde and a C-Nuc form

Answer 11

Primary alcohol

Question 12

What does an aldehyde and a C-Nuc form

Answer 12

A secondary alcohol

Question 13

What does an ketone and a C-Nuc form

Answer 13

tertiary alcohol

Question 14

What is the mechanism for adding an organolithium compound to a carbonyl group

Answer 14

Li attacks C onto O making covalent bond between O and Li. O attacks H of H3O turning it into an alcohol

Question 15

What is an acetylide anion

Answer 15

CH triple bonded to C covalently bonded to Na

Question 16

What is the mechanism fro adding acetylide anions to a carbonyl group

Answer 16

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

Question 17

What is the mechanism for adding cyanide to a carbonyl group

Answer 17

C lone pair attacks C onto O. O attacks H of another cyanide onto the C making a cyanohydrin

Question 18

What is the mechanism for the formation of a wittig reagent

Answer 18

Ph3P attack CH3I onto I which covalently bonds to Ph3P. Butylithium attacks H of CH3 onto Carbon forming butane, a phosphonium ylide, and LiI

Question 19

What is the mechanism of a Wittig reaction

Answer 19

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

Question 20

What does the addition of water to a carbonyl make

Answer 20

Hydrate (C bonded to two hydroxyls)

Question 21

What is the mechanism for adding an alcohol to a carbonyl group

Answer 21

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

Question 22

What is the mechanism for using acetal as a protecting group of a carbonyl

Answer 22

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

Question 23

What is the mechanism for the addition of ammonia to a carbonyl group

Answer 23

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

Question 24

What is the mechanism for adding NaBH3 to a carbonyl group

Answer 24

H attacks C onto O. O attacks H forming alcohol