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Synthesis Questions For Revision

This document provides synthesis questions to help with revision of organic functional groups and families. It lists various functional groups and compounds and asks the reader to provide reaction sequences to synthesize compounds from given starting materials, including ethanol, benzene, and 1-bromobutane. Hints reference relevant chapters in lecture notes containing useful reactions. Additional practice is suggested by finding other compounds that can be made in no more than two steps from the given starting materials.

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Stella Chea
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54 views11 pages

Synthesis Questions For Revision

This document provides synthesis questions to help with revision of organic functional groups and families. It lists various functional groups and compounds and asks the reader to provide reaction sequences to synthesize compounds from given starting materials, including ethanol, benzene, and 1-bromobutane. Hints reference relevant chapters in lecture notes containing useful reactions. Additional practice is suggested by finding other compounds that can be made in no more than two steps from the given starting materials.

Uploaded by

Stella Chea
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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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.

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