Chapter 18

Question 1

Addn of Hydride to Aldehydes and Ketones

Answer 1

Reagents: NaBH4 (can be mixed with CH3OH), LAH (LiAlH4) stronger
-H protonates O
-O- attacks H to get and OH

Question 2

Imine Reaction (c double bond N)

Answer 2

-reduced to an amine
-can use NaBH4 or LAH

Question 3

Nitrile Reaction (C triple bond N)

Answer 3

-reduced to an Amine
-Can ONLY use LAH or will not work

Question 4

Addn of Organometallic Reagents

Answer 4

(R-Li or R-MgBr)

Question 5

Aldehyde/Ketone Organometallic

Answer 5

R group attacks C–O making new bond and O-
-H+ protonates the O-

Question 6

Nitrile Organometallic

Answer 6

-R group attacks the C double O
-Spilts bond into an o- and the R group
-H protonates OH creating Carboxylic acid

Question 7

Compatibility of R- and H when other functional groups are present

Answer 7

If r-OH, an epoxide, or an organohalide is present
-wanted reaction will NOT occur

Question 8

Conjugate Addition (Michael Addn)

Answer 8

-alpha-beta unsaturated C–O
-Weaker Nu (CN, R-O, X-, Enolate, Gilman Reagent (rzCuLi)
-Lose C–C bone and R- bonded to the beta carbon

Question 9

Direct Addn

Answer 9

Super strong Nu
(H-, R-, NaBH4, LAH, R-MHBR)
-Nu attacks C–O

Question 10

The Wittig RXN

Answer 10

-Converts an Aldehyde or Ketone to an Alkene
-PPH3
-so C–O turns into C–C and rest of chain is added on