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1

17.30d What Grignard reagent and what carbonyl compound might you start with to prepare the following alcohol?

2

17.30e) What Grignard reagent and what carbonyl compound might you start with
to prepare the following alcohols?

3

17.35 How would you prepare the following compounds from 2­phenylethanol?
More than one step may be required.

(answer a-e)

4

17.35 How would you prepare the following compounds from 2­-phenylethanol?
More than one step may be required.

(answer f-h)

5

17.33 d How would you synthesize the following alcohols,starting with benzene and other alcohols of six or fewer carbons as your only organic reagents?

6

What reagents transform:

Ketone → ROH

 

i) LiAlH4 in ether; ii) H3O+

or

NaBH4 in ethanol

7

What reagents transform:

ROH → Ketone

 

Na2Cr2O7 in H2SO4 (aq.)

or

 PCC or DMP

8

What reagents transform:

 Alkoxide Salt  → ROH

 

(ie: RO- Li+)

 H3O+

9

What reagents transform:

ROH → Alkoxide Salt

Na or NaH in an ether

10

What reagents transform:

ROH   → Alkene 

 Concentrated H2SO4 or H3PO4, ∆

(tertiary only)

11

What reagents transform:

 Alkene  → ROH

 i) B2H6 in ether; ii) H2O2, NaOH (aq.)

or

i) Hg(OAc)2 in H2O; ii) NaBH4 in ethanol. 

12

What reagents transform:

ROH → Alkyl Halide

HBr, HI, HCl+ZnCl2, SOCl2, PBr3 (1˚/2˚ only)

13

What reagents transform:

ROH → Alkane

(1˚ and 2˚ only)
  1. HBr, HI, HCl+ZnCl2, SOCl2, PBr3 
  2. Mg in ether
  3. H3O+

or

(1˚ only)

1. ArSO3Cl in pyridine (TOSYL!)
    [or HBr, HI, HCl+ZnCl2, SOCl2, PBr3]

2. i) LiAlH4 in ether; ii) H3O+

14

What reagents transform:

Carboxylic Acid  → ROH

i) LiAlH4 in ether; ii) H3O+

15

What reagents transform:

Aldehyde →  ROH

PCC or DMP

16

What reagents transform:

ROH → Aldehyde

i) LiAlH4 in ether; ii) H3O+

or

NaBH4 in ethanol.

17

What reagents transform:

ROH → Carboxylic Acid

Na2Cr2O7 in H2SO4 (aq.)

18

What reagents transform:

ROH → Sulfonate Ester

ArSO3Cl in pyridine (TOSYL!)

19

What reagents transform:

ROH → Ether

  • Na or NaH in an ether
  • 1°-alkyl halide or tosylate

20

Give the product of the following reaction

21

What is the product when 

(CH3)3COH 

is mixed with 

Na2Cr2O7 in H2SO4?

No Reaction!

22

Synthesize:

cyclopentanol → trans-2-methylcyclopentanol

23