chapter 28 synthesis

Question 1

how to increase carbon chain length (nitrile) ?

aliphatic

Answer 1

• Haloalkanes or carbonyls
• carbonyl + NaCN + H2SO4 (rather than HCN due to it being safer + increased rate) - nucleophillic addition
• Haloalkane + NACN + ethanol - nucleophilic substititution

Question 2

how to increase carbon chain length (benzene)

aromatic

Answer 2

• alkylation - alkyl group from haloalkane to benzene ring, AlCl3 catalyst needed
• acyation - benzene reacts with acyl chloride with AlCl3 catalyst to form a ketone

Question 3

how to get from alkane to haloalkane ?

conditions + reagents

Answer 3

• halogen + UV

Question 4

how to get from alkene to alkane ?

conditions + reagents

Answer 4

• H2 + Ni catalysst

Question 5

how to get from alkene to haloalkane ?

conditions + reagents

Answer 5

• Hydrogen halide

Question 6

how to get from alkene to alcohol ?

conditions + reagents

Answer 6

• H2O (steam) + H3PO4 catalyst

Question 7

how to get from alcohol to alkene ?

conditions + reagents

Answer 7

• H3PO4 OR H2SO4 under reflux

Question 8

how to get from primary alcohol to aldehyde ?

conditions + reagents

Answer 8

• K2Cr2O7 with H2SO4 catalyst while distilling product
• forms aldehyde and H2O

Question 9

how to get from primary alcohol to Carboxylic acid ?

conditions + reagents

Answer 9

• K2Cr2O7 with H2SO4 catalyst under reflux
• forms CA and H2O

Question 10

how to get from secondary alcohol to Ketone ?

conditions + reagents

Answer 10

• K2Cr2O7 with H2SO4 catalyst under reflux

Question 11

how to get from alcohol to ester ?

conditions + reagents

Answer 11

• carboxylic acid / acid anhydride + conc H2SO4 catalyst

Question 12

how to get from alcohol to Haloalkane ?

conditions + reagents

Answer 12

• sodium halide + H2SO4 catalyst

Question 13

how to get from Haloalkane to alcohol ?

conditions + reagents

Answer 13

• NaOH (aq)

Question 14

how to get from Haloalkane to Nitrile ?

conditions + reagents

Answer 14

• CN- + ethanol

Question 15

how to get from Haloalkane to amine ?

conditions + reagents

Answer 15

• NH3 + ethanol

Question 16

how to get from nitrile to amine ?

conditions + reagents

Answer 16

• H2 + Ni catalyst

Question 17

how to get from nitrile to carboxylic acid ?

conditions + reagents

Answer 17

• H2O + HCl + heat under reflux

Question 18

how to get from ketone to hydroxynitrile ?

conditions + reagents

Answer 18

• NaCN(aq) under acid conditions

Question 19

how to get from aldehyde to hydroxynitrile ?

conditions + reagents

Answer 19

• NaCN(aq) under acid conditions

Question 20

how to get from carboxylic acid to ester ?

conditions + reagents

Answer 20

• alcohol + conc H2SO4

Question 21

how to get from carboxylic acid to Acyl chloride ?

conditions + reagents

Answer 21

• SOCl2

Question 22

how to get from ester to carboxylate ?

conditions + reagents

Answer 22

• OH- + heat reflux

Question 23

how to get from acyl chloride to amide ?

conditions + reagents

Answer 23

• NH3 / Primary amide / secondary amide

Question 24

how to get from benzene to nitrobenzene ?

conditions + reagents

Answer 24

• conc HNO3 + conc H2S04

Question 25

how to get from **benzene to alkylbenzene** ? | conditions + reagents

Answer 25

* chloroalalkane + AlCl3

Question 26

how to get from **benzene to aromartic ketone** ? | conditions + reagents

Answer 26

* acyl chloride + AlCl3

Question 27

how to get from **aromatic ketone to secondary alcohol** ? | conditions + reagents

Answer 27

* NaBH4

Question 28

how to get from **nitrobenzne to phenyl amine** ? | conditions + reagents

Answer 28

* Sn + conc HCl

Question 29

Which reactions require **heating under reflux** ?

Answer 29

* CA from primary alcohol * ketones from secondary alcohol * dehydration of alcohols * substitution of alcohols

Question 30

What are the **components of quick fit apparatus** ?

Answer 30

1. round bottom / pear shaped flask 2. receiver 3. Screw-tap adaptor 4. Condenser 5. Still head

Question 31

What do you need **for heating under reflux** ?

Answer 31

* round bottom / pear shaped flask * condenser * rubber tubing * stand and clamp * heat source * anti-bumping granules

Question 32

What is **distillation used for** ?

Answer 32

**purifying a pure liquid from its impurities** * involved in making aldehydes, cracking alkenes

Question 33

What do you need **for distillation** ?

Answer 33

Question 34

How to **purify organic products** (separating funnel) ?

Answer 34

1. Pour organic mixture in separating funnel, ensure tap is closed 2. Inverted to mix and allow layers to settle 3. Use conical flask to empty the contents 4. Wash organic product with water 5. Add drying agent - anhydrous CaSO4 6. Obtain dry organic product

Question 35

what is **recrystalisation** ?

Answer 35

* when the solid product isnt pure and impurities need to be removed * a **hot solvent is used to dissolve both the organic solid and the impurities, as the soluution cools the colid crystalises out and leaves inpuurities in soluution** * minimum ammount of solvent to dissolve the solid * crystals can be removed by filtration

Question 36

how does **recrystalisation work** ?

Answer 36