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Chemistry Mine > (yellow) organic analysis and synthesis > Flashcards

(yellow) organic analysis and synthesis Flashcards

(yellow) organic analysis and synthesis

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1
Q

what are some compounds that absorb water . therefore can be used to measure water absorbtion

A

anhydrdrous calcium chloride or anhydrdrous copper sulphate (II)

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2
Q

if a organic compound is burnt under a flame and produces a clean blue flame what is it

A

alcohol

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3
Q

if a organic compound is burnt under a flame and produces a yellow flame what is it

A

alkane

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4
Q

if a organic compound is burnt under a flame and produces a smoky yellow flame what is it

A

unstaurated / aromatic

*(may need to edit later)
carbon composition is greater in unsaturated compounds therefore this leads to more oxygen being used, which causes less oxygen in the surrounding enviroment leading to incomplete combusiton

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5
Q

comment on the solubility of hydrocarbens

A

no soluable immiscuble forming two layers

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6
Q

comment on the solubility of alcohols

A

dipole , forms hydrogen bonds

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7
Q

comment on the solubility of carboxilic acids and amine

A

very soluable , H0bonding

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8
Q

what are the observations when you put an alkene with bromine water

A

goes from brown to colourless and produces a H and Br neighbours on the double bond carbon

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9
Q

what are the observations when you put an alkene with KMnO4 / H2SO4

A

purple to colourless
also produces two dioles (oh x 2)

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10
Q

how do you go from a nitrile R-CN to a R-CH2-NH2

A

LiAlH4 in dry ether

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11
Q

how do you go from a nitrile R-CN to a carboxilic group

A

dil HCl which causes hydrolisation

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12
Q

how do you go from a halogeno alkane to a nitrile

A

KCN in ethanol which acts as a solvent has to be in alkali conditions

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13
Q

what would happen if you added KCN or HCN to a ketone

A

you would produce a hydroxy nitrile

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14
Q

how would you go from a hydroxy nitrile R-C(OHCN) - R to a carboxilic group and alcohol group R-C(OHCOOH) - R

A

dil HCl

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15
Q

how would you go from a hydroxy nitrile R-C(OHCN) - R to a reduced CH2-NH2 group instead of the CN gorup

A

LiALH4 in dry ether

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16
Q

Alkene to Halogenoalkane

type of reaction , reagent and conditions

A

Halogen or Hydrogen Halid

addition

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17
Q

type of reaction , reagent and conditions

alkene to alkane

A

Hydrogen and Pt/Pd catalyst

addition

reduction

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18
Q

type of reaction , reagent and conditions

alkene to alcohol

A

Steam and acid catalyst (phosphoric acid)

addition

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19
Q

type of reaction , reagent and conditions

alkene to diol

A

KMnO4/dil NaOH, cold KMnO4/dil H2SO4, warm

addition

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20
Q

type of reaction , reagent and conditions

carbonyl to hydroxynitrile

A

HCN and KCN

addition

21
Q

type of reaction , reagent and conditions

alkane to Halogenoalkane

A

Halogen and UV light

substitution

22
Q

type of reaction , reagent and conditions

Halogenoalkane to alcohol

A

NaOH(aq)

sub

23
Q

type of reaction , reagent and conditions

Halogenoalkane to nitrile

A

KCN (ethanol)

sub

24
Q

type of reaction , reagent and conditions

Halogenoalkane to amine

A

NH3 (ethanol)

sub

25
Q

type of reaction , reagent and conditions

Alcohol to Halogenoalkane

A

PCl5 / PBr3 /PI3 or HCl / HBr (made in situ)

sub

26
Q

type of reaction , reagent and conditions

Acyl chloride to Carboxylic acid

A

H2O

SUB

27
Q

type of reaction , reagent and conditions

Acyl chloride to ester

A

alcohol

SUB

28
Q

type of reaction , reagent and conditions

Acyl chloride to Amide

A

Ammonia

SUB

29
Q

type of reaction , reagent and conditions

Acyl chloride to N sub amide

A

amine

30
Q

type of reaction , reagent and conditions

1.Alkene to diol

A

KMnO4 + acid

oxidation

31
Q

type of reaction , reagent and conditions

Aldehyde to carboxilic acids

A

K2Cr2O7 + Sulfuric acid or Tollens or Fehling

oxidation

32
Q

type of reaction , reagent and conditions

nitrile to amine

A

LiAlH4 (dry ether) or H2 & Catalyst

reduction

33
Q

type of reaction , reagent and conditions

. Carboxylic acid + alcohol to ester

A

Acid catalyst

condensation

34
Q

type of reaction , reagent and conditions

3.Acid chlorides + H2O, ROH, NH3, RNH2 to Carboxylic acid, ester, (N-subs)amide

A

Dry

oxidation

35
Q

type of reaction , reagent and conditions

Halogenoalkane to alkene

A

Con KOH (ethanol) heat under reflux

elimination

36
Q

type of reaction , reagent and conditions

alocohols to alkene

A

Con Sulphuric acid and high temp

eliminaiton

37
Q

type of reaction , reagent and conditions

Carboxylic acid + alkali to salt + water

A

Room temp

acid / base

38
Q

type of reaction , reagent and conditions

Amine + HCl to alkyl ammonium salt

A

Room temp

acid / base

39
Q

type of reaction , reagent and conditions

Benzene to Bromobenzene

A

FeBr3 and Br2

SUB

40
Q

type of reaction , reagent and conditions

Benzene to Nitrobenzene

A

Con H2SO4 and Con HNO3 Heat under reflux

SUB

41
Q

type of reaction , reagent and conditions

Benzene to Alkylbenzene

A

Halogenoalkane & AlCl3 Heat under reflux

SUB

42
Q

type of reaction , reagent and conditions

Benzene to Alkylbenzene

A

Acyl Chloride & AlCl3 Heat under reflux

SUB

43
Q

type of reaction , reagent and conditions

Phenol to 2 4 6 tribromophenol

A

Bromine water

44
Q

read

A

Other points to consider when choosing a route

Yields

The fewer steps the better – why?

· Organic reactions seldom produce a yield of >50%.

· The products requires often have to be separated before the next stage.

How easy will it be to separate the product

· It is usually easier to separate and purify solid products.

· Recrystallisation of solids or fractional distillation of liquids

Isomerism Will isomers be formed? Which types of reactions result in isomer formation?

· Addition reactions when Nucleophilic Addition. Racemic mixtures due to addition to a planar starting material

· Substitution reactions e.g. SN1 Racemic mix due to planar intermediate carbocation SN2 optical product only one direction to attach C delta +ve

· Elimination reactions e.g.to form cis or trans products

Why is the formation of isomers a problem in synthesis?

· May result in different products in subsequent reactions

· Biological systems require stereo-specific molecules

45
Q

how does mass spec work and what are its key principals

A

how it works

High energy electrons bombard sample knocking off an electron. Also possible fragmentation

Key information gained

Molecular weight value from m/z Formula from High resolution Mass spec with M/z values to 4 dp Stable fragments have high percentage abundance

46
Q

how does IR work and what are its key principals

A

how it works
IR radiation absorbed by sample causes bonds to vibrate etc. Must be polar bonds.

key information :
Below 1500 wavenumbers fingerprint region can be used to identify compound. Above 1500 can be used with data book to give information about the bonds which are present

47
Q

how does C NMR work and what are its key principals

A

how it works :

Radio waves absorbed by sample

key info :

No of C in different environments – no of peaks Chemical shift – the nature of the C environmen

48
Q

how does H NMR work and what are its key principals

A

how it works

Radio waves cause H nuclei to flip to a high energy state

key info :
No of H in different envionments by o of peaks Area under curve – No of H in each environment Chemical shift – the nature of the H environment High resolution Splitting pattern - The number in adjacent inequivalent H’s ie the n+1 rule

49
Q

what is the basic function of recystalisation and also what is its steps

A

basic function : product is soluable in hot solvent but not in cold solvent

1 . min qualintaty of solvent added to impure substance

  1. warmed to dissolve substance , insoluable impuritys left
  2. Hot filtration removes insoluable inpuritys
  3. allow to cool and substance crystallises out leaving soluable impuritys in
  4. filter off crystalls rinse and dry

rinse : rinses out in cold solvent so impuritys dissolve

dry : oven or between two filter papers

Chemistry Mine (35 decks)

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