Chapter 11

Question 1

Define alcohol

Answer 1

An OH attached to a carbon

Question 2

Define benzyl alcohol

Answer 2

OH attached to a carbon that is attached to a benzene ring

Question 3

Define phenol

Answer 3

OH attached to a benzene ring

Question 4

Define enol

Answer 4

OH attached to a double bond

Question 5

Describe how to name alcohols

Answer 5

Select the longest chain with the OH, number from the end closest to the OH
A benzene ring without a H is a phenyl group

Question 6

Define ether

Answer 6

An oxygen single bonded to two carbons

Question 7

Describe the two ways to name ethers

Answer 7

Name the two alkyl groups, followed by the name ether
Alkyl groups are in alphabetical order
Ex: Isopropyl methyl ether

Name them as alkoxy alkanes
Name the ether as a substituent of the main chain
“Alkyl group attached to the O”oxy
Ex: 3-methoxypentane

Question 8

Describe how to name cyclic ethers

Answer 8

Start name with Oxa
Cyclopropane-> Oxacyclopropane
Ex: 1,4-dioxacyclohexane

Question 9

Define diol

Answer 9

A compound containing two OH groups

Question 10

Describe how to name diols

Answer 10

Remember to indicate cis/trans
Indicate the positions of the OH groups with numbers
Ending is diol (for the two OH groups)

Question 11

Describe acid-catalyzed hydration (review from chapter 8)

Answer 11

Alkene + H+/H2O -> Add H, Rearrange, Add OH

Question 12

Describe oxymercuration/demercuration (review from chapter 8)

Answer 12

Alkene + Hg(OAc)2/H2O/THF + NaBH4/Base -> Anti-addition of OH to most substituted side

Question 13

Describe hydroboration/oxidation (review from chapter 8)

Answer 13

Alkene + BH3/THF + H2O2/NaOH -> OH syn to least substituted

Question 14

What possible product(s) will be produced when you add HX to an alcohol? Include sterochemistry, if relevant.

Answer 14

ROH + HX -> RX + H2O, with inversion (methyl and 1* alcohols)

Add H to make OH into Water, remove water to form a carbocation, Rearrangements, Add X (2, 3, allyic, and benzylic alcohols)

Question 15

What possible product(s) will be produced when you add PBr3 to an alcohol? Include sterochemistry, if relevant.

Answer 15

3 ROH + PBr3 -> 3 RBr + H3PO3, with inversion

Only works with methyl, 1, and 2* alcohols

Question 16

What possible product(s) will be produced when you add SOCl2 to an alcohol? Include sterochemistry, if relevant.

Answer 16

ROH + SOCl2 -> RCl + SO2 + HCl, with inversion

Only works with methyl, 1, and 2* alcohols

Question 17

What possible product(s) will be produced when you add TsCl or MsCl to an alcohol? Include sterochemistry, if relevant.

Answer 17

ROH + TsCl -(Et3N or Pyridine)-> ROTs + Et3NHCl

This is done to convert OH to a good leaving group

Question 18

Describe how you synthesize symmetric ethers

Answer 18

ROH + ROH -(H+/heat)-> ROR + H2O

Question 19

Describe how you synthesize unsymmetric ethers

Answer 19

RONa + RX -(SN2)-> ROR + NaX

Works with methyl and 1* halides

Question 20

Describe how you synthesize tert-butyl ethers

Answer 20

RCH2-OH + CH2=C(CH3)CH3 (2-methyl-1-propene) -(H2SO4)-> (CH3)3C-O-CH2R
(A hydrogen changes the CH2 to a CH3 on 2-methyl-1-propene, creating a carbocation on the middle carbon. The oxygen on the RCH2-OH bonds to that carbocation, and then the Hydrogen leaves)

Question 21

Describe how you synthesize silyl ethers

Answer 21

ROH + ClSi(Me)3 -(base such as Et3N or pyridine)-> ROSiMe3 + Et3NHCl

Question 22

What possible product(s) will be produced when you add one equivalent of HX to a symmetric ether? Include sterochemistry, if relevant.

Answer 22

ROR + 1 HBr -(heat)-> HOR + RBr

Question 23

What possible product(s) will be produced when you add two equivalents of HX to a symmetric ether? Include sterochemistry, if relevant.

Answer 23

ROR + 2 HBr -(heat)-> 2RBr + H2O

*HOR from first equivalent reacts to form H2O and RBr

Question 24

What possible product(s) will be produced when you add HX to an unsymmetric ether? Include sterochemistry, if relevant.

Answer 24

One side is tertiary/benzylic/allylic -> that side will grab the X in an SN1,

If not it will go via SN2 (X on the least substituted carbon on the opposite side, produce alcohol and inverted alkyl halide)

Question 25

Describe how you synthesize epoxides

Answer 25

Alkene + Peracid (-CO3H) -> Add O across double bond (cis-alkene yields one meso product, trans-alkene yields enantiomers)

Question 26

What possible product(s) will be produced when you add a nucleophile to an epoxide? Include sterochemistry, if relevant.

Answer 26

Ring will open on the less substituted side, that side will accept the base, quench the reaction with H+ to add an H to the O

End up with base on less substituted side, and an H on the O
(Nucleophile will attack the least bulky side, bond between least bulky side and O will break, quenched with the addition of a H to the O)

Base and OH are anti

Question 27

What possible product(s) will be produced when you add acid to an epoxide? Include sterochemistry, if relevant.

Answer 27

Protonate O, H2O attacks most substituted carbon, another H2O grabs a H from the first

End up with conjugate base on more substituted side and an H on the O

(The H of the Acid is added to the O, the water will attack the most substituted side, the bond between the most substituted side and the O breaks, A H leaves the water, forming a trans molecule with two OH)

Conjugate base and OH are anti