Further organics

Question 1

delocalised model of benzene

Answer 1

the p-orbital of the 6 C overlap to form a delocalised π system.

Question 2

Electron density

Answer 2

a representation of the probability of finding an electron at a specific point around an atom/ molecule.

Question 3

electron-donating groups

Answer 3

donate e- into ring when attached to C and are 2,4 directing

Question 4

define
electron withdrawing groups

Answer 4

groups which pull electron density away from ring, and 3 directing

Question 5

Halogen carrier

Answer 5

A lewis acid that can bind to a halogen molecule, weakening the halogen bond to form a electrophile

Question 6

What does phenol not react to?

Answer 6

Carbonates

Question 7

Kekule’s Benzene Model

Answer 7

model of benzene which contains C=C and C-C bonds

Question 8

3 evidence of the delocalised model

Answer 8

1. bond length
2. enthalpy change of hydrogenation
3. resistance to reaction

Question 9

3 steps to general electrophilic sub. of benzene

Answer 9

1. generation of electrophile
2. substitution
3. catalyst reformation

Question 10

Effect of addition reaction of benzene

Answer 10

1. aromaticity is lost
2. stability of the ring is lost

Question 11

electrophile for nitration of benzene

Answer 11

NO2 +

Question 12

Halogen carriers for halogenation of benzene

Answer 12

AlCl3
FeBr3

Question 13

4 types of electrophilic substitution of benzene

Answer 13

1. halogenation
2. nitration
3. Acylation (COCl)
4. alkylation (CH3)

Question 14

why is phenol more reactive than benzene

Answer 14

1. greater charge density
2. more suspetible to electrophile attack

Question 15

Directing points
of electron-donating groups

Answer 15

2,4,6

Question 16

Directing points of
electron-withdrawing groups

Answer 16

3

Question 17

3 E.g. of electron-donating group

Answer 17

CH3 , OH , NH3

Question 18

Eq. for
formation of Acyl chloride

Answer 18

Carboxylic acid +

Carboxylic acid +

Question 19

How to make ester with phenol

Answer 19

acyl chloride

NOT carboxylic acid

Question 20

What is acyl chloride more reactive than?

Answer 20

1. acid anhydride
2. COOH
3. OH

Question 21

4 reagents that reacts with
acyl chloride

state product as well …

Answer 21

+ Alcohol -> ester
+ water -> COOH
+ ammonia -> 1’ amine
+ 1’ amine -> amide

Question 22

what is the product when
acid anhydride + alcohol

Answer 22

carboxylic acid
+ ester

Question 23

Which is the most efficient way to produce
ester

+ why?

Answer 23

acid anhydride + alcohol

as it’s irreversible

Question 24

Define chiralty

Answer 24

An isomerism when C is bonded to 4 different groups

Question 25

How to form amide

Answer 25

acyl choride + amine

Question 26

How to name 2' amine/amide

Answer 26

Suffix - side attached to C=O Preffix - side attached to N-H (+ N- ) | preffix = stuff substituted on Nitrogen

Question 27

Name below

Answer 27

N-methly ethanamide

Question 28

Methods to extend backbone (aliphatic)

Answer 28

1. haloalkane + NaCN 2. carbonyls + NaCN + H+

Question 29

2 Reactions to eliminate nitrile group | name products

Answer 29

1. reduction -> Amine 2. hydrolysis -> Alcohol

Question 30

Extend backbone for aromatic

Answer 30

1. acylation 2. alkylation

Question 31

Eq for hydrolysis of nitrile

Answer 31

Question 32

Eq. for the reduction of nitrile

Answer 32

Question 33

5 steps for recrytallisation

Answer 33

1. dissolve in min. vol. of hot solvent 2. let it cool 3. filter with vaccum filtration 4. wash with cold solvent 5. let it dry

Question 34

2 steps for nitrobenzene -> phenyl amine

Answer 34

1. Sn + HCl (conc.) 2. NaOH

Question 35

# synthesis route reduction of carbonyls | reagent + condition

Answer 35

NaBH4 + H2O

Question 36

Eq. for formation of amine | from haloalkane

Answer 36

Haloalkane + ethanoic ammonia -> amine + HX

Question 37

reagent needed | nitrile -> amine

Answer 37

H2 + Ni

Question 38

Product for alkali hydrolysis | ester / amide

Answer 38

Carboxylate salt + Alcohol / amine

Question 39

Reagents for alkylation

Answer 39

Haloalkane + halogen carrier

Question 40

Reagent for aclylation

Answer 40

Acyl chloride + halogen carrier

Question 41

Test for carbonyls

Answer 41

1. Add 2,4 DNP positive = yellow/orange p.p.

Question 42

Test for aldehyde

Answer 42

1. tollen's reagent silver p.p.

Question 43

Test for haloalkane

Answer 43

1. AgNO3 + NH3 same color for p.p. in halogen tests

Question 44

Range for Rf value

Answer 44

0< Rf < 1

Question 45

4 functional groups that make molecule **polared **

Answer 45

1. OH 2. C=O 3. COOH 4. NH2

Question 46

what does retention time tell | In gas chromo

Answer 46

the time for sample to react detector Shorter time = more soluble in mobile phase = less soluble in liquid phase

Question 47

What are GC and TLC for

Answer 47

GC - volatile liquid / gases TLC - solids

Question 48

What is TMS | proton NMR

Answer 48

standard for chemical shifts measurements | proton NMR

Question 49

What is CDCl3 and its purpose?

Answer 49

1. deuterated solvents dissolve organic molecules without hydrogen

Question 50

3 things to consider when observing proton NMR spec

Answer 50

1. area under 2. shifts 3. coupling

Question 51

What does not couple | proton NMR

Answer 51

1. equivilent H 2. OH 3. NH2

Question 52

Purpose of proton exchange

Answer 52

removes OH and NH peaks

Question 53

How to do proton exchange ?

Answer 53

1. do normal NMR 2. add D2O 3. redo NMR [replaces H in OH/NH2 to OD/ND2]

Question 54

no. of peaks if 1/2/3 non-equivilent H next door

Answer 54

2 peaks (d, doublet) 3 peaks (t, triplet) 4 peaks (q, quartet)

Question 55

Define enantiomer

Answer 55

non-superimposable mirror image