9-Alcohols, Ethers, and Epoxides

Question 1

Increasing intermolecular forces

Answer 1

CH3CH2CH2CH3 > CH3OCH2CH3 > CH3CH3CH3OH

Question 2

Increasing ability to hydrogen bond (increases/decreases) boiling point

Answer 2

Increasing ability to hydrogen bond INCREASES boiling point

Question 3

Increasing intermolecular forces (increases/decreases) boiling point

Answer 3

Increasing intermolecular forces INCREASES boiling point

Question 4

When are alcohols, ethers, and epoxides water soluble?

Answer 4

When they have less than 5C’s per O atom

Question 5

When are alcohols, ethers, and epoxides water soluble?

Answer 5

When they have more than 5C’s per O atom

Question 6

Are alcohols, ethers and epoxides soluble in organic solvents?

Answer 6

yes

Question 7

Alcohols: Increasing rate of reaction with HX

Answer 7

More substituted alcohols react more rapidly

RCH2-OH < R2CH-OH < R3C-OH

Question 8

Alcohols: increasing reactivity of hydrogen halides

Answer 8

increases with acidity

H-CL < H-Br < H-I

Question 9

rxn: ROH -> RCL
reagent: HCL

Answer 9

• useful for all ROH
• 2* and 3*ROH -> Sn1 (racemic)
• CH3-OH and 1*ROH -> Sn2 (inversion)

Question 10

rxn: ROH -> RCL
reagent: SOCl2

Answer 10

• best for CH3OH and 1* and 2*ROH

- Sn2 (inversion)

Question 11

rxn: ROH -> RBr
reagent: HBr

Answer 11

• useful for all ROH
• 2* and 3*ROH -> Sn1 (racemic)
• CH3-OH and 1*ROH -> Sn2 (inversion)

Question 12

rxn: ROH -> RBr
reagent: PBr3

Answer 12

• best for CH3OH and 1* and 2*ROH

- Sn2 (inversion)

Question 13

rxn: ROH -> RI
reagent: HI

Answer 13

• useful for all ROH
• 2* and 3*ROH -> Sn1 (racemic)
• CH3-OH and 1*ROH -> Sn2 (inversion)