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Chemistry > Further organics > Flashcards

Further organics Flashcards

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1
Q

delocalised model of benzene

A

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

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2
Q

Electron density

A

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

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3
Q

electron-donating groups

A

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

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4
Q

define
electron withdrawing groups

A

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

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5
Q

Halogen carrier

A

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

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6
Q

What does phenol not react to?

A

Carbonates

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7
Q

Kekule’s Benzene Model

A

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

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8
Q

3 evidence of the delocalised model

A
  1. bond length
  2. enthalpy change of hydrogenation
  3. resistance to reaction
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9
Q

3 steps to general electrophilic sub. of benzene

A
  1. generation of electrophile
  2. substitution
  3. catalyst reformation
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10
Q

Effect of addition reaction of benzene

A
  1. aromaticity is lost
  2. stability of the ring is lost
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11
Q

electrophile for nitration of benzene

A

NO2 +

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12
Q

Halogen carriers for halogenation of benzene

A

AlCl3
FeBr3

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13
Q

4 types of electrophilic substitution of benzene

A
  1. halogenation
  2. nitration
  3. Acylation (COCl)
  4. alkylation (CH3)
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14
Q

why is phenol more reactive than benzene

A
  1. greater charge density
  2. more suspetible to electrophile attack
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15
Q

Directing points
of electron-donating groups

A

2,4,6

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16
Q

Directing points of
electron-withdrawing groups

A

3

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17
Q

3 E.g. of electron-donating group

A

CH3 , OH , NH3

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18
Q

Eq. for
formation of Acyl chloride

A

Carboxylic acid +

Carboxylic acid +

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19
Q

How to make ester with phenol

A

acyl chloride

NOT carboxylic acid

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20
Q

What is acyl chloride more reactive than?

A
  1. acid anhydride
  2. COOH
  3. OH
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21
Q

4 reagents that reacts with
acyl chloride

state product as well …

A

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

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22
Q

what is the product when
acid anhydride + alcohol

A

carboxylic acid
+ ester

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23
Q

Which is the most efficient way to produce
ester

+ why?

A

acid anhydride + alcohol

as it’s irreversible

24
Q

Define chiralty

A

An isomerism when C is bonded to 4 different groups

25
Q

How to form amide

A

acyl choride
+
amine

26
Q

How to name 2’ amine/amide

A

Suffix - side attached to C=O
Preffix - side attached to N-H
(+ N- )

preffix = stuff substituted on Nitrogen

27
Q

Name below

A

N-methly ethanamide

28
Q

Methods to extend backbone
(aliphatic)

A
  1. haloalkane + NaCN
  2. carbonyls + NaCN + H+
29
Q

2 Reactions to eliminate
nitrile group

name products

A
  1. reduction -> Amine
  2. hydrolysis -> Alcohol
30
Q

Extend backbone
for aromatic

A
  1. acylation
  2. alkylation
31
Q

Eq for hydrolysis of nitrile

A
32
Q

Eq. for the reduction of
nitrile

A
33
Q

5 steps for
recrytallisation

A
  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
34
Q

2 steps for
nitrobenzene -> phenyl amine

A
  1. Sn + HCl (conc.)
  2. NaOH
35
Q

synthesis route

reduction of carbonyls

reagent + condition

A

NaBH4 + H2O

36
Q

Eq. for
formation of amine

from haloalkane

A

Haloalkane + ethanoic ammonia
->
amine + HX

37
Q

reagent needed

nitrile -> amine

A

H2 + Ni

38
Q

Product for alkali hydrolysis

ester / amide

A

Carboxylate salt
+
Alcohol / amine

39
Q

Reagents for alkylation

A

Haloalkane + halogen carrier

40
Q

Reagent for aclylation

A

Acyl chloride
+
halogen carrier

41
Q

Test for carbonyls

A
  1. Add 2,4 DNP

positive = yellow/orange p.p.

42
Q

Test for aldehyde

A
  1. tollen’s reagent

silver p.p.

43
Q

Test for haloalkane

A
  1. AgNO3 + NH3

same color for p.p. in halogen tests

44
Q

Range for Rf value

A

0< Rf < 1

45
Q

4 functional groups that make molecule **polared **

A
  1. OH
  2. C=O
  3. COOH
  4. NH2
46
Q

what does retention time tell

In gas chromo

A

the time for sample to react detector

Shorter time
= more soluble in mobile phase
= less soluble in liquid phase

47
Q

What are GC and TLC for

A

GC - volatile liquid / gases
TLC - solids

48
Q

What is TMS

proton NMR

A

standard for chemical shifts measurements

proton NMR

49
Q

What is CDCl3 and its purpose?

A
  1. deuterated solvents

dissolve organic molecules without hydrogen

50
Q

3 things to consider when observing proton NMR spec

A
  1. area under
  2. shifts
  3. coupling
51
Q

What does not couple

proton NMR

A
  1. equivilent H
  2. OH
  3. NH2
52
Q

Purpose of
proton exchange

A

removes OH and NH peaks

53
Q

How to do proton exchange ?

A
  1. do normal NMR
  2. add D2O
  3. redo NMR

[replaces H in OH/NH2 to OD/ND2]

54
Q

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

A

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

55
Q

Define enantiomer

A

non-superimposable mirror image

Chemistry (6 decks)

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