Chapter 17

Question 1

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

Answer 1

Question 2

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

Answer 2

Question 3

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

(answer a-e)

Answer 3

Question 4

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

(answer f-h)

Answer 4

Question 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?

Answer 5

Question 6

What reagents transform:

Ketone → ROH

Answer 6

i) LiAlH4 in ether; ii) H3O+

or

NaBH4 in ethanol

Question 7

What reagents transform:

ROH → Ketone

Answer 7

Na₂Cr₂O₇ in H₂SO₄ (aq.)

or

PCC or DMP

Question 8

What reagents transform:

** Alkoxide Salt ** → ROH

(ie: RO^- Li⁺)

Answer 8

H3O+

Question 9

What reagents transform:

ROH → Alkoxide Salt

Answer 9

Na or NaH in an ether

Question 10

What reagents transform:

**ROH ** → **Alkene **

Answer 10

Concentrated H2SO4 or H3PO4, ∆

(tertiary only)

Question 11

What reagents transform:

** Alkene ** → ROH

Answer 11

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

or

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

Question 12

What reagents transform:

ROH → Alkyl Halide

Answer 12

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

Question 13

What reagents transform:

ROH → Alkane

Answer 13

(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+

Question 14

What reagents transform:

**Carboxylic Acid ** → ROH

Answer 14

i) LiAlH4 in ether; ii) H3O+

Question 15

What reagents transform:

Aldehyde** → **ROH

Answer 15

PCC or DMP

Question 16

What reagents transform:

ROH → Aldehyde

Answer 16

i) LiAlH4 in ether; ii) H3O+

or

NaBH4 in ethanol.

Question 17

What reagents transform:

ROH → Carboxylic Acid

Answer 17

Na₂Cr₂O₇ in H₂SO₄ (aq.)

Question 18

What reagents transform:

ROH → Sulfonate Ester

Answer 18

ArSO3Cl in pyridine (TOSYL!)

Question 19

What reagents transform:

ROH → Ether

Answer 19

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

Question 20

Give the product of the following reaction

Answer 20

Question 21

What is the product when

(CH₃)₃COH

is mixed with

Na₂Cr₂O₇ in H₂SO₄?

Answer 21

No Reaction!

Question 22

Synthesize:

cyclopentanol → trans-2-methylcyclopentanol

Answer 22