synthesis questions

for revision
organic 1 functional groups and families
These families are discussed under their own chapter headings,
lecture 5-10.

5. haloalkanes
6a. alcohols
6b. ethers
acid chlorides
7. Aldehydes and ketones
anhydrides
8. carboxylic acid derivatives
esters
9. amines
amides
10 and 11. aromatic compounds
organic 1 functional groups and families
These families have been discussed under other topic headings,
as follows:
nitriles R-C≡N
9. haloalkanes (SN2 reactions)
11. aldehydes and ketones (cyanohydrins)
12. carboxylic acid derivatives (hydrolysis to amides & carboxylic acids)
13. amines (reduction to 1° amines)
16. arenediazonium salts (with CuCN - conversion to arenenitriles)
imines R2C=N-R
aldehydes and ketones (oximes, DNP)
aldehydes and ketones (Wolff-Kishner reduction)
amines (reduction to 1°, 2° or 3° amines)
sulfonic acid derivatives
14. benzenesulfonic acids (sulfonation of benzenes)
10. sulfonate esters - alcohols (SN1 and SN2 reactions of tosylates)
13. sulfonamides - amines (Hinsberg test)
reagents and reactions
acids: bases:
HCl NaOH, KOH
HBr NaOR, KOH in ethanol
HI NaNH2
H2SO4 RMgX
HNO3 pyridine
reactions forming C-C bonds: inorganic sources of 1 carbon units:
Wurtz (Na + RX) CO2
Organocopper (R2CuLi + RX) CN- or HCN
nitrile (KCN + RX, >C=O or >C=NH)
Simmons-Smith (CH2I2/Zn,Cu+ >C=C<)
Grignard (RMgX + >C=O, CO2 or ethylene oxide)
Friedel-Crafts alkylation (ArH + R+)
Friedel-Crafts acylation (ArH + RC≡O+)
 reagents and reactions
oxidants: reductants:
Mn(VII): KMnO4 H2 / Pt, Pd
Cr(VI): K2Cr2O7 CrO3 PCC H2 / Pd, BaSO4 (Lindlar)
Cl2 , Br2 , I2 NaBH4
LiAlH4
H3PO2 (hypophosphorous acid)
(Na)
others: (Mg)
H 2 O / H+
H2O / OH−
SOCl2 ; PBr3 ; P / I2
p-toluenesulfonyl chloride
benzenesulfonyl chloride
ammonia
hydroxylamine, DNP
organic synthesis
You have as possible starting materials:
ethanol, benzene, 1-bromobutane
Any necessary inorganic reagents can be used.
Write a reaction sequence* to show how you would prepare:

3. ethanal 6

* Write two or more alternatives sequences if you can.

organic synthesis
You have as possible starting materials:
ethanol, benzene, 1-bromobutane
Any necessary inorganic reagents can be used.
Write a reaction sequence* to show how you would prepare:

4. bromoethane 5

5. 1,2-dibromoethane 4

6. diethyl ether 6

* Write two or more alternatives sequences if you can.

organic synthesis
You have as possible starting materials:
ethanol, benzene, 1-bromobutane
Any necessary inorganic reagents can be used.
Write a reaction sequence* to show how you would prepare:

7. acetic acid 6

8. pentanoic acid 8

9. butyl acetate 8

* Write two or more alternatives sequences if you can.

organic synthesis
You have as possible starting materials:
ethanol, benzene, 1-bromobutane
Any necessary inorganic reagents can be used.
Write a reaction sequence* to show how you would prepare:

10. 1-butanamine 8

11. 1-pentanamine 8

12. N-ethylpropylamine 8

* Write two or more alternatives sequences if you can.

organic synthesis
You have as possible starting materials:
ethanol, benzene, 1-bromobutane
Any necessary inorganic reagents can be used.
Write a reaction sequence* to show how you would prepare:

13. ethylbenzene10 and 11

15. benzoic acid 10 & 11

16. p-ethylbenzoic acid 10& 11

* Write two or more alternatives sequences if you can.

organic synthesis
Hints 6-20:

chapters of the lecture notes in which to look for useful reactions

For more practice, find more compounds that can be prepared from
these starting materials in no more than 2 steps?
You have as possible starting materials:
ethanol, benzene, 1-bromobutane
Any necessary inorganic reagents can be used.