Exam 3

Question 1

Grignard (R-MgX) and 1.CO2, 2.H2O

Answer 1

Makes a carboxylic acid by first adding Mg to the existing R group on the molecule such as a phenyl ring with Br. Then Mg attacks C and creates carboxylic acid where Mg was.

Question 2

Cuprates 1.(R2CuLi) 2. H2O

Answer 2

Adds only one R group except it adds it to the beta position which is the second carbon away from the carbonyl. This is only when there is a carbonyl and double bond. Prefers C=C. If there is no other double bond then changes carbonyl to OH and R group.

Question 3

Grignards 1.(R-MgCl) 2.H2O

Answer 3

Grignards don’t care about alpha and beta. They only react with the carbonyl, changing it to an OH and an R group.

Question 4

Hydrogenation 1.NaBH4 2.H2O

Answer 4

Changes carbonyl to OH and H. Not chemoselective

Question 5

H2(1 equiv), Pd/C

Answer 5

Pd is chemoselective for C=C so ignores carbonyl and adds an H to each side of double bond

Question 6

H2(excess), Pd/C

Answer 6

Causes a total reduction but C=C goes first. So adds one H to each side of double bond then changes carbonyl to OH and H.

Question 7

Radical Halogenation (Br2, 🔺)

Answer 7

All Alkanes must start with this! Adds a Br

Question 8

DBU or DBN or KotBu

Answer 8

Elimination. Turns Br into Double bond inside the ring

Question 9

Hydration (H2SO4, H2O)

Answer 9

Changes Alkene into Alkane with OH

Question 10

K2Cr4O7 or PCC or CrO3,H2SO4, H2O

Answer 10

Changes OH into carbonyl

Question 11

1.CH3MgBr 2. H2O

Answer 11

Changes carbonyl into OH and CH3

Can make grignard from HOCH3 and PBr3. Then you get BrCH3 then you add Mg•

Question 12

H2SO4, H2O or POCl3

Answer 12

Causes elimination of the OH but not the R group

Question 13

ToSCl and pyridine

Answer 13

Changes OH to OTs

Question 14

HBr, HCl or PBr3, SOCl2

Answer 14

Changes OH into X

Question 15

PCC or Cr3O3, H2SO4, H2O
Or K2Cr4O7
Or Na2Cr4O7

Answer 15

Changes OH into carbonyl

Question 16

H2SO4, H2O or POCl3

Answer 16

Eliminates OH changing alkane to alkene

Question 17

1. NaBH4 2. H2O or
2. LiAlH4 2. H2O
   with a aldehyde or ketone

Answer 17

Becomes primary alcohol (R connected to OH) if SM is aldehyde
Becomes secondary alcohol (Two Rs and an OH) if SM is a ketone

Question 18

Organometallic (Li-CH3 or Li-R or Na-C triple bond C-R

Answer 18

Changes carbonyl to OH and whatever the “R” group is connected to the metal.

Question 19

NaCN, HCN

Answer 19

Changes carbonyl into cyanohydrin. (OH group and CN) (keep existing groups from carbonyl always for everything)

Question 20

H2O, H+(generic acid) or H2O,OH- (generic base)

reacting with a cyanohydrin (something with CN)

Answer 20

Adds a carboxylic acid to the C in the C triple bond N. N disappears

Question 21

Wittig Reaction (Ph3P=R)

Answer 21

Gets rid of O on starting material, adds C instead and rest of R group attached to the Ph3P.
(Replaces carbonyl with its own double bond and junk) creates a biproduct of O=Ph3P
When doing retrosynthesis, want to put Ph3P on one with fewer R groups
Add O to one with most R group to make carbonyl and add PPh3 to other one

Question 22

Primary amine and “mild acid”, or H+, H3O+, or HA

Answer 22

Primary amine has one C directly attached to it.
Causes a imine and (H2O) (two H goes into the H2O)
Imine is one that looks like a carbonyl just with an N instead of an O. N acts as glue for the two pieces.

Question 23

Secondary amine and “mild acid”, or H+, or H3O+, or HA

Answer 23

N replaces O on carbonyl and act like glue to hold all the pieces together. Creates enamine, weird side alkene. (Bi product is still H2O) creates from H2 leaving N and O leaving carbonyl.)

Question 24

Hydrolysis of imines.

Imine and H2O, H+

Answer 24

Turns imine into both original parts. Adds O to double bond where N was and takes off N and R group in a chunk then add H2 to N

Question 25

H2O excess

Answer 25

Changes carbonyl into two OH groups ( keeps original bottom groups)

Question 26

H3COH excess, H+ ( usually TsOH)

Answer 26

Turns carbonyl into two OCH3 groups

Question 27

OHROH, H+ with carbonyl

Answer 27

Makes cyclic acetal by splitting carbonyl into two Os and adding however many carbons are in the R group to make ring

Question 28

Acetals hydrolysis (H2O, H2SO4)

Answer 28

Turns two Os or OCH3 groups to come together into carbonyl. If H is present turns into aldehyde if not turns into ketone.

Question 29

Cyclic hemiacetals (H+)

Answer 29

OH group turns into just an O, carbonyl turns into OH and you count the number of spots for ring. Don’t count the H at the end. Then form ring.

Question 30

Any leaving group with a Nu

Answer 30

Carbonyl kicks leaving group and replaces it with Nu. Keeps Carbonyl.