Ch 10 Reactions

Question 1

Alkyl Halide –> Alcohol

Answer 1

SN2 reaction

Question 2

Alkene –> Least substituted alcohol

Answer 2

1) BH3*THF 2) HOOH, NaOH

Question 3

Alkene –> Most substituted alcohol

Answer 3

1) Hg(OAc)2, H20 2) NaBH4

Question 4

Alkene –> cis-Diol

Answer 4

OsO4 or cold, dilute KMnO4, NaOH, H2O

Question 5

Alkene –> trans-Diol

Answer 5

Peroxyacid in H2O

Question 6

Terminal alkyne –> Primary alcohol

Answer 6

1) Generate acetylide 2) React with formaldehyde

Question 7

Terminal alkyne –> Secondary alcohol

Answer 7

1) Generate acetylide 2) React with aldehyde

Question 8

Terminal alkyne –> Tertiary alcohol

Answer 8

1) Generate acetylide 2) React with ketone

Question 9

Formaldehyde –> Primary alcohol (2 reagents)

Answer 9

1) Grignard or organolithium 2) aqueous wkup

Question 10

Aldehyde –> Secondary alcohol (2 reagents)

Answer 10

1) Grignard or organolithium 2) aqueous wkup

Question 11

Ketone –> Tertiary alcohol (2 reagents)

Answer 11

1) Grignard or organolithium 2) aqueous wkup

Question 12

Ester or Acid Halide –> Tertiary alcohol (2 reagents)

Answer 12

1) Grignard or organolithium 2) aqueous wkup

Question 13

Epoxide –> Alcohol (most substituted carbon of the epoxide)

Answer 13

Acid-catalyzed opening

Question 14

Epoxide –> Alcohol (least substituted carbon of the epoxide)

Answer 14

Base-catalyzed opening

Question 15

Aldehyde –> Primary alcohol

Answer 15

LAH or NaBH4, aqueous wkup

Question 16

Ketone –> Secondary alcohol

Answer 16

LAH or NaBH4, aqueous wkup

Question 17

Ester –> Primary alcohol

Answer 17

2eq LAH, aqueous wkup

Question 18

Carboxylic acid –> Primary alcohol

Answer 18

3 eq LAH, aqueous wkup

Question 19

Alkyl halide –> Lithium dialkyl cuprate

Answer 19

2 eq RLi + CuI

Question 20

Coupling of two aklyl groups

Answer 20

1) Create R2CuLi 2) React with alkyl halide