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CHEMISTRY > Organic > Flashcards

Organic Flashcards

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1
Q

What is the bond angle in alkanes?

A

109 1/2 °

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2
Q

What is the equation for calculating the percentage composition of an element?

A

% composition = (mass of all the atoms of that element in the molecule/ relative molecular mass) x 100

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3
Q

What is empirical formula?

A

The simplest whole-number ratio of the atoms in a molecule

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4
Q

What is the general formula of an alkane?

A

CnH2n +2

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5
Q

What is the general formula for an alkene?

A

CnH2n

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6
Q

What is the general formula for alkynes?

A

CnH2n -2

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7
Q

What is the general formula for cycloalkanes?

A

CnH2n

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8
Q

What is the general formula for cycloalkenes?

A

CnH2n -2

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9
Q

What are the steps of combustion data calculations?

A

1/ Divide grams of CO2 and H2O produced by their respective molecular mass

2/ Times the calculated amount of H2O by 2 as there are two atoms of H

3/ Divide by the smallest amount of the new totals. This should give a ratio

4/ Convert the ratios into whole-number forms by multiplying by an appropriate amount

4/

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10
Q

What is the equation for combustion of methane?

A

CH4(g) + 2O2(g) –> CO2(g) + 2H2O(g)

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11
Q

What are the two possible products, besides water, of the partial combustion of methane?

A

CO(g) and C(s)

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12
Q

What type of reaction is the splitting up of two molecules of the same element?

A

Homolytic fission

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13
Q

What is cracking?

A

The breaking down of a large chained alkane into a smaller chain alkane and an alkene

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14
Q

What are alkenes?

A

Unsaturated hydrocarbons with a π bond

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15
Q

What is the bond angle in alkenes?

A

120°

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16
Q

Why do alkenes have geometrical isomerism?

A

There is a lack of free rotation about the π bond when there are two different groups at each end of the double bond

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17
Q 
H                H
   \             /
     C  =  C
    /          \ 
 Cl           Cl

What type of geometrical isomerism is this?

A

Cis / Z

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18
Q 
H               Cl
   \             /
     C  =  C
    /          \ 
 Cl           H

What type of geometrical isomerism is this?

A

Trans / E

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19
Q

Give an equation for the hydrogenation of propene?

What is the catalyst for this reaction?

A

C3H6 + H2 —> C3H8

Nickel

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20
Q

What are the conditions for addition of HX to an alkene?

A

Room temperature

Concentrated solution of HX

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21
Q

What kind of reaction is the addition of HX to an alkene?

A

Electrophilic addition

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22
Q

Conditions for reacting an alkene with Br2

Give an equation and what this can be used to test for

A

Room temperature

C2H4 + Br2 –> C2H4Br2

Can test for the presence of a C=C bond

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23
Q

What is unusual about the reaction of Br2 with an alkene compared to the same reaction with chlorine?

A

A bride forms when using Br2 so the mechanism is slightly different

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24
Q

What is Markornikoff’s rule and what does it apply to?

A

The reaction of HX with an alkene

  • The hydrogen of HX adds to the carbon which already has the most hydrogens
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25
Q

If Cl2 is non-polar, how does it react with an alkene?

A

The Cl2 becomes polarised as it approaches the electron rich double bond

26
Q

What are the conditions for an alkene reacting with water?

What does it produce?

Give an equation

A
  • Water must be as steam
  • 600K
  • 6 Mpa (60 atm)
  • Catalyst of H3PO4 (phosphoric acid)
  • inert support

An alcohol

C2H4 + H2O —> CH3CH2OH

27
Q

How would you synthesise a haloalkane from an alkene?

Give an equation

A

React with conc. HX at room temperature

C2H4 + HBr —> CH3CH2Br

28
Q

What are the equations for synthesising a halogenoalkane from an alcohol?

A

CH3CH2OH + HBr —> CH3CH2Br + H20

3CH3CH2OH + PI3 —> 3CH3CHI + H3PO3

CH3CH2OH + PCl5 —> CH3CH2Cl + POCl3 + HCl

CH3CH2OH + SOCl2 —-> CH3CH2Cl + SO2 + HCl

29
Q

How would you synthesise an alcohol from a halogenoalkane?

Give an example

A

Stir the halogenoalkane with dilute aqueous alkali at room temperature
H2O
CH3CH2Br + NaOH ——–> CH3CH2OH + NaBr

30
Q

What is the reactivity order for carbons bonded to a halogen?

A

C-I > C-Br > C-Cl&raquo_space; C-F

31
Q

What are the characteristics of an SN2 reaction?

A
  • occurs in primary and some secondary halogenoalkanes but not tertiary

Rate ∝ [RX] [Nucleophile]

Both the RX and the nucleophile are involved in the rate determining step

32
Q

Which is faster: SN1 or SN2?

A

SN1

33
Q

What are the characteristics of an SN1 reaction?

A

Fast

Rate ∝ [RX]

Only the concentration of the halogenoalkane is involved in the rate determining step

Can produce stereoisomers if halogenoalkane is chiral

34
Q

When are SN1 reactions favoured?

A

Favoured in tertiary molecules

When using polar protic solvents

35
Q

When are SN2 reactions favoured?

A

In primary molecules

When using polar aprotic solvents

36
Q

What are non-polar aprotic solvents?

Give an example

A
  • Do not contain polar O-H or N-H groups

- Hydrocarbons

37
Q

What are polar aprotic solvents?

Give examples

A

Polar molecules that cannot hydrogen bond

  • CH3CN
  • Me2CO
  • DMF
  • DMSO
38
Q

What are polar protic solvents?

Give examples

A

Contain polar O-H or N-H groups and can hydrogen bond

  • H2O
  • CH3CH2OH
  • Liquid NH3
39
Q

Describe the conditions for reacting a halogenoalkane with ammonia

Give an equation

A
  • heat the halogenoalkane with excess ammonia in an ethanolic solution
                                 CH3CH2OH CH3CH2BR + NH3  -------------------> CH3CH2NH2 + HBr

This produces an amine

40
Q

What are the conditions for reacting a halogenoalkane with cyanide?

What type of reaction is it?

Give an equation

A
  • Heat the halogenoalkane with an alcoholic KCN solution

Substitution (techniqely addition)

(CH3)2 CHBr + KCN —–> (CH3)2 CHCN + NaBr

41
Q

What can the product of reacting a halogenoalkane alkane with cyanide be reduced to?

Give an equation

A

A primary amine

(CH3)2CHCN —-> (CH3)2CHCH2NH2

42
Q

Describe the elimination reactions of halogenoalkanes

A
  • Involve heating the halogenoalkane with concentrated ethanolic alkali
  • HX is removed from the molecule
                  NaOH/C2H5OH CH3CH2Br ------------------------> C2H4 + CH3CH2OH + Br- 
                      Reflux
43
Q

Describe the E2 reaction

Give the rate equation

A
  • Bonds make and break at the same time

Rate ∝ [RX] [BASE]

44
Q

Describe the E1 reaction

Give the rate equation

A
  • bonds make and break in different steps
  • Most substituted alkene is the favoured product
  • E-isomers are favoured on steric grounds

Rate ∝ [RX]

45
Q

When are elimination reactions favoured?

A
  • using alcoholic solutions
  • high temperatures
  • using secondary or tertiary halides
  • using polar solvents
46
Q

Give the general equation of the reaction of a halogenoalkane with silver nitrate solution

A

RX + H2O —-> ROH + H+ + X-

Ag + X- ——> AgX(s)

47
Q

Describe the different reactions of halogenoalkanes reacting with AgNO3 solution

A

1-chlorobutane slow white (AgCl)

1-bromobutane medium cream (AgBr)

1-iodobutane fast yellow (AgI)

48
Q

What are the physical properties of alcohols?

A
  • Very polar O-H bonds
  • Hydrogen bonding leads to high boiling temperatures
  • Ethanol is miscible with water but from butanol upwards, alcohols are not miscible
49
Q

Describe the reaction of fermentation

Give an equation

A
  • Anaerobic
  • requires yeast
  • 35°C

C6H12O6 ——> 2CO2 + 2C2H5OH

50
Q

How would you produce a halogenoalkane from an alcohol?

Give all equations

A

Heat with a mixture of NaBr and conc. H2SO4

NaBr + H2SO4 —–> NaHSO4 + HBr

CH3CH2OH + HBr ——-> CH3CH2BR + H2O

51
Q

Give all of the equations of ethanol reacting with phosphorus halides

A

3 CH3CH2OH + PCl3 —–> 3 CH3CH2Cl + H3PO3

CH3CH2OH + PCl5 ———> CH3CH2Cl + POCl3 + HCl

3 CH3CH2OH + PBr3 ——-> 3 CH3CH2Br + H3PO3

3 CH3CH2OH + PI3 ——–> 3 CH3CH2I + H3PO3

52
Q

Describe a test for an OH group

Give an equation

What can be observed?

A

Reacting an alcohol with PCl5

CH3CH2OH + PCl5 —–> CH3CH2Cl + POCl5 + HCl

White, misty fumes

53
Q

Describe a reaction of ethanol with SOCl2

A

Reacts at room temperature

CH3CH2OH + SOCl2 ——> CH3CH2Cl + HCl + SO2

Misty fumes of HCl and SO2 can be seen

54
Q

Give an equation for the reaction of ethanol with sodium

A

2 CH3CH2OH + 2Na —–> 2 CH3CH2O- Na+ (s) + H2

55
Q

How would you form an alkene from an alcohol?

A

Dehydration reaction

Pass alcohol over hot Al2O3 at 400°C

Heat with excess conc. H2SO4

CH3CH2OH —-> C2H4 + H2O

56
Q

How would you produce an ester from an alcohol?

Give an equation

A

Heat with a carboxylic acid

Acid catalyst (conc. H2SO4)

CH3CH2COOH + CH3CH2OH CH3CH2COOCH2CH3
+ H2O

57
Q

How are esters named?

A

1st part from the alcohol

2nd part from the acid

eg ethyl propanonate

58
Q

What are the benefits of using an acyl chloride to produce an ester?

A
  • reacts in the cold

- reaction isn’t reversible

59
Q

Give the equation for the production of an ester using an acyl chloride

A

CH3COCL + CH3CH2OH —-> CH3COOCH2CH3 + HCl

60
Q

How would you oxidse an alcohol?

What will you see?

A

Use acidified potassium dichromate (VI) solution (K2Cr2O7/H2SO4)

Colour change from orange to green

61
Q

How would you produce an aldehyde from an alcohol?

Give the equation

A

Use PCC in CH2Cl2 solution

                   PCC/CH2CL2 CH3CH2OH ----------------------- CH3CH2O

CHEMISTRY (18 decks)

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