Organic Chemistry 2 Flashcards

1
Q

alkene –> markovnikov alkyl halide

A

H-X

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2
Q

alkene –> anti-markovnikov alkyl halide

A

H-Br, peroxides

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3
Q

alkene –> markovnikov alcohol

A

H20, H+

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4
Q

alkene —> anti-markovnikov alcohol

A

1) BH3*THF, 2) H2O2, OH-

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5
Q

alkene —> syn addition alkane

A

H2 and Pt, Pd, or Ni

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6
Q

alkene –> anti addition alkyl dihalide

A

X2

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7
Q

alkene —> anti addition markovnikov halohydrin

A

X2, H20

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8
Q

alkene –> epoxide

A

peroxyacid, example: MCPBA

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9
Q

epoxide –> anti gycol

A

H+, H2O

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10
Q

alkene –> anti glycol

A

1) peroxyacid, 2) H+ H2O

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11
Q

alkene —> syn glycol

A

KMnO4 (cold, dilute), OH-, H2O

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12
Q

alkene –> syn glycol

A

OsO4 , H2O2

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13
Q

Alkene –>ozonide

A

O3

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14
Q

ozonide –> ketones and aldehydes

A

(CH3)2S

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15
Q

alkene —> ketones and aldehydes

A

1) O3, 2) (CH3)2S

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16
Q

alkene –> ketones and acids

A

KMnO4 (warm)

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17
Q

acetylide —> acetylide anion

A

NaNH2

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18
Q

acetylide anion —>alkyne

A

R-X

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19
Q

acetylide anion —> alcohol

A

carbonyl group containing compound (formaldehyde, aldehyde, or ketone)

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20
Q

alkyne —> alkane

A

2H2, Pt, Pd, or Ni

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21
Q

alkyne –> cis alkene

A

H2, Pd/BaSO4, quinoline (lindlar’s catalyst)

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22
Q

alkyne –> trans alkene

A

Na, NH3

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23
Q

alkyne –> haloalkane (4 X)

A

2X2

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24
Q

alkyne —> geminal haloalkane (markovnikov)

A

2 H-X

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25
Q

alkyne —> (vinyl alcohol ketone), markovnikov

A

HgSO4, H2SO4

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26
Q

alkyne —> (vinyl alcohol aldehyde), anti-markovnikov

A

1)SiaBH*THF, 2) H2O2, NaOH

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27
Q

alkyne –> alpha-diketone

A

KMnO4, H2O, Neutral

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28
Q

alkyne —> carboxylic acids

A

O3, H2O

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29
Q

alkene + H-X

A

markovnikov alkyl halide

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30
Q

alkene + H-Br –peroxides->

A

anti-markovnikov alkyl halide

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31
Q

alkene + water –H+->

A

markovnikov alcohol

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32
Q

alkene + 1)BH3*THF, 2)H2O2, OH-

A

anti-markovnikov alcohol

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33
Q

alkene +H2 –Pt,Pd, or Ni->

A

syn addition alkane

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34
Q

alkene + X2

A

anti addition alkyl dihalide

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35
Q

alkene + peroxyacid

A

syn addition epoxide + carboxylic acid

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36
Q

epoxide —H+, H2O->

A

anti glycol

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37
Q

alkene —1)peroxyacid, 2)H+, H2O->

A

anti glycol

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38
Q

alkene + KMnO4 (cold, dilute) —OH-, H2O->

A

syn glycol

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39
Q

alkene + OsO4 —H2O2 ->

A

syn glycol

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40
Q

alkene + O3

A

ozonide

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41
Q

ozonide –(CH3)2S

A

ketones and aldehydes

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42
Q

alkene + KMnO4(warm)

A

ketones and acids

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43
Q

acetylide + NaNH2

A

acetylide anion + Na+ + NH3

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44
Q

acetylide anion + R-X

A

alkyne molecule with desired R group

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45
Q

acetylide anion + R2C=O

A

alcohol

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46
Q

alkyne + 2H2 –Pt, Pd, or Ni ->

A

alkane

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47
Q

alkyne + H2 —Pd/BaSO4, quinoline (lindlar’s catalyst) –>

A

cis alkene

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48
Q

alkyne – Na, NH3 –>

A

trans alkene

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49
Q

alkyne + 2X2

A

haloalkane, 4 halogens

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50
Q

alkyne + 2H-X

A

geminal haloalkane, Markovnikov

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51
Q

alkyne – HgSO4, H2SO4–>

A

vinyl alcohol ketone , markovnikov

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52
Q

alkyne –1) SiaBH*THF, 2) H2O2, NaOH –>

A

vinyl alcohol aldehyde, anti-markovnikov

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53
Q

alkyne + KMnO4 —H2O, Neutral ->

A

alpha-diketone

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54
Q

alykne –1) KMnO4, OH-, 2) H+ –>

A

carboxyilic acids

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55
Q

alkyne –O3, H2O –>

A

carboxylic acids

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56
Q

What happens when you have a carboxylic acids with a salt?

A

No REACTION because it already has a negative charge

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57
Q

List, in order of decreasing basicity, the charged nucleophiles that are on the table in the blue sheet.

A

CH3-, NH2-, OH-, OR-, SH-/SR-, -OAc, Cl- (X-)

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58
Q

How would you remember the order of the charged nucleophiles?

A

Come Now Oliver Over Shore Over Clapping

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59
Q

What is capable of reacting with a carboxyllic acid? (Which charged nucleophile(s)?

A

CH3-, NH2-, OH, SH, -OAc

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60
Q

What would the LG be in the above case?

A

The H would bond with the nucleophiles, leaving the carboxylic O with a negative charge

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61
Q

How do you know when you can have a reaction with a charged nucleophile?

A

As long as the LG is MORE stable than the Nucleophile, the reaction WILL happen

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62
Q

Is the same true for salts, though?

A

Yes

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63
Q

What is the product of an acyl halides (carboxyllic with a Cl instead of an O at the far right) with a charged nucleophile?

A

Carboxyllic acid

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64
Q

What are the charged nucleophiles that are capable of carrying out this reaction? What is the LG of this reaction?

A

All of them “Cl”

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65
Q

What first happens to the acyl chloride before the reaction takes place (Before it is attacked with the nucleophile?)

A

It forms a resonance form with a positive charge on the Carbon and negative on oxygen

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66
Q

What is the name of the reaction of acyl chlorides with nucleophiles?

A

Acyl addition elimination (for biochem)

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67
Q

What does the reaction of anhydrides and nucleopiles yeild? What is the LG?

A

Carboxylic acids, LG = “RCOO-“

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68
Q

What are the charged nucleophiles that can react with the ESTER? What is the LG??

A

CH3- and the NH2- LG is the OR-

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69
Q

What are the charged nucleophiles that can react with a primary amide? What is the LG?

A

CH3- LG is NH2

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70
Q

What does the reduction of aldehydes and ketones yeild?

A

Alcohols

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71
Q

What are the reagents required for the carbonyls (aldehydes and ketone) reaction?

A

NaBH4–Sodium boronhydride and LiALH4, LithiumAluminum Hydride

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72
Q

What is the first steop of the carbonyl reaction?

A

The reagent gives a hydride to the central carbon atom, giving the oxygen a negative charge

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73
Q

What is the second stop of the carbonyl reaction?

A

dilute acid gives the negatively charged oxygen an H to stabalize the charge

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74
Q

What is the only functional group capable of reacting with a carboxyllic acid to form a salt?

A

strong base neutral nucleophiles can react to form a salt (O of carb. acid has a negative charge

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75
Q

What is fisher esterfication?

A

It is when a carb. acid reacts with a weak base to form water and an ester or anhydride

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76
Q

FE is to what and Salts are to what?

A

FE is to weak base and salts are to strong base

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77
Q

What is the order of reactivity of addition elimination reactions? IN DECREASING REACTIVITY

A

Acyl halides, anhydrides, esters and amides

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78
Q

What do all derivatives yield upon hydrolysis?

A

Carboxylic acids

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79
Q

What is hydrolysis:

A

Acid/water or base/water followed by acidification

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80
Q

PREPARATION SECTION OF TEST

A

PREPARATION SECTION OF TEST

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81
Q

What is needed for the oxidation of aromatic side chains at the benzyl position?

A

Strong oxidizing agents like hot HNO3 or KMnO4

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82
Q

What solvents are needed for oxidation of primary alcohols?

A

KMnO4 or CrO3, H2SO Chromic Acid

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83
Q

Solvent needed for oxidation of aldehydes?

A

KMnO4

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84
Q

How do you know what the product of the preparation of acids is?

A

It is usually the main compuund, like a benzene ring minus its attachments, but instead of its old attachments, it has the COOH

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85
Q

What are the solvents needed for carbonation of grignard reagents?

A

Make grignard reagent by MG metal, add CO2, then acidify with H+

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86
Q

Nitrile hydrolysis requires what?

A

Nitrile is first formed by Sn2 reaction on an alkyl bromide( from alcohols and HBr combination)

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87
Q

Second step?

A

KCN adds

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88
Q

Third step?

A

Water, dilute acid, or water and OH-

89
Q

What’s the product?

A

R COOH

90
Q

What is needed for the hydrolysis of acyl derivatives?

A

Hydrolysis with water (plus acid or base)

91
Q

Acid chlorides and water give what products?

A

carb. acid and HCl

92
Q

Anhydrides and water yeild what?

A

2 equivalents of carb. acid

93
Q

What do esters need to form carb. acid and alcohol?

A

Water/acid

94
Q

What is this hydrolysis reaction called in a base?

A

Saponification

95
Q

What is the last step of saponification?

A

Forming NEUTRAL acid by acid an acidification step

96
Q

Amides will form RCOOH and an amine with what solvent?

A

WATER

97
Q

PREPARATION OF CARB ACID DERIVATIVES

A

PREPARATION OF CARB ACID DERIVATIVES

98
Q

How do you form acid chlorides? What solvents are needed, I mean.

A

Carb. Acids and Thionyl chloride (SOCL2) and Phosphorus trichloride (PCl3)

99
Q

What solvents are needed to form anhydrides?

A

Pyridine (with acid chlorides and carb. acids or RCOOH salt) or Heat (with carb. acids and loss of water)

100
Q

What solvents are needed to form esters?

A

Fisher esterfication (Conc. H+, RCOOH, Alcohol), Acid chlorides and an alcohol, Anhydrides an analcohol

101
Q

How will amides form?

A

Acid chlorides and an amine

102
Q

How will amides and alcohols form?

A

Esters and an amine

103
Q

How will salts and amides form?

A

Anhydrides and an amine

104
Q

REDUCTION OF RCOOH AND DERIVATIVES

A

REDUCTION OF RCOOH AND DERIVATIVES

105
Q

Esters will be reduced, how?

A

LAH (LiAlH4), followed by acidification yields two equivalents of alcohol

106
Q

How will amides will be reduced

A

LAH, neutralization with acid yields an amine

107
Q

Nitriles are also known as what?

A

Cyanides

108
Q

How will nitriles be reduced

A

LAH, neutrilization with acid forms an amine

109
Q

How else can amines form by reduction?

A

reduction with H2 and Pt or Pd

110
Q

How will RCOOH be reduced?

A

LAH, acidification yeilds a primary alcohol

111
Q

How will all reactions with neutral nucleophiles (Except for what) work?

A

Except for with amides, all other functional groups, the LG will be the larger group, it will look like a grignard reaction, the LG will be the largest molecules connected together

112
Q

What will the amide reaction with netural nucleophile Water look like?

A

You will get an NH4 and salt because it’s an acid-base reaction

113
Q

A reaction of an amide with another amide will give?

A

a fifty-fifty mixture

114
Q

FACTORS AFFECTING BASICITY AND ACIDITY

A

FACTORS AFFECTING BASICITY AND ACIDITY

115
Q

What are the three factors that impact the acid and base properties?

A

Hybridization, inductance, resonance

116
Q

What type of hybridization makes a strong base?

A

SP3, less s character

117
Q

What type of inductance makes a strong base?

A

lower left hand compounds, less electronegative groups, but additing electron donating group

118
Q

What are electron donating groups?

A

CH3- and other alkyl groups

119
Q

What affect does resonance have on amines?

A

Aromatic amines have resonance forms and their resonance forms spread electrons around ring, amking e- less available to react=weaker base

120
Q

why are amides even worse bases than aromatic amine?

A

first order equal to second order

121
Q

To have an amide, you need…

A

a c double bond O must be directy attached to nitrogen

122
Q

What is the acidity of an amid?

A

very very acidic. PKA 0

123
Q

What are the steps of saponification?

A

First, get resonance intermediate by moving double bond, then have nucleophile attack, then get rid of negative charge on O and have leaving group leave, then have the LG grab the H on the molecule….the last step is getting rid of the negative charge

124
Q

Aldehydes are prepared by the oxidation of a

A

primary alcohol

125
Q

an organic group containing one or more -CHO groups

A

aldehyde

126
Q

What is the functional group for the aldehydes?

A

carbonyl group (-CHO)

127
Q

general formula for the aldehydes

A

R-CHO

128
Q

where is the functional group located on the carbon chain for the aldehydes?

A

at the end of the carbon chain

129
Q

methyl alcohol oxidizes to form

A

formaldehyde

130
Q

the molecular formula for formaldehyde

A

HCHO

131
Q

another name for formaldehyde

A

methanal

132
Q

a three-carbon chain aldehyde would be called

A

propanal

133
Q

formaldehyde in water is known as

A

formalin

134
Q

formalin is what percentage aqueous solution of formaldehyde by weight?

A

37%

135
Q

formalin is what percentage aqueous solution of formaldehyde by volume?

A

40%

136
Q

formed by the oxidation of ethanol, a two carbon chain aldehyde

A

acetaldehyde

137
Q

another name for acetaldehyde

A

ethanal

138
Q

a benzene derivative in which one of the hydrogens in the ring is replaced with an aldehyde group

A

benzaldehyde

139
Q

benzaldehyde is known as an

A

aromatic aldehyde

140
Q

an aldehyde with two aldehyde group (having a carbonyl group at each end of the carbon chain)

A

dialdehydes

141
Q

the simplest dialdehyde is

A

glyoxal

142
Q

two examples of dialdehydes

A

glyoxal and glutaraldehyde

143
Q

the oxidation of a secondary alcohol yields a

A

ketone

144
Q

the general formula for a ketone is

A

RCOR

145
Q

a ketone has two ____ groups attached to a ___ group

A

two alkyl groups attached to a carbonyl group

146
Q

the simplest ketone is

A

propanone

147
Q

propanone is also known as (2)

A

acetone, dimethyl ketone

148
Q

the general formula for carboxylic acids

A

R-COOH

149
Q

the functional group in a carboxylic acid is known as a

A

carboxyl group

150
Q

two examples of carboxylic acids

A

methanoic acid, ethanoic acid

151
Q

another name for methanoic acid

A

formic acid

152
Q

another name for ethanoic acid

A

acetic acid

153
Q

_____ oxidize for form organic acids

A

aldehydes

154
Q

_____ oxidizes to form formic acid (also means _____ oxidizes to form ____ acid)

A

formaldehyde (methanal, methanoic)

155
Q

_____ oxidizes to form acetic acid (also means ____ oxidizes to form ____ acid)

A

acetaldehyde (ethanal, ethanoic)

156
Q

general formula for esters

A

R-COO-R

157
Q

two examples of esters

A

ethyl acetate, methyl salicylate

158
Q

a colorless liquid that has a characteristic smell like certain glues or nail polish removers

A

ethyl acetate

159
Q

ethyl acetate is derived from ____ and _____

A

ethanol and acetic acid

160
Q

known as oil of wintergreen, a natural product of many species of plants

A

methyl salicylate

161
Q

methyl salicylate is derived from _____ and _____

A

methanol and salicylic acid

162
Q

derived from an alcohol and an organic acid

A

esters

163
Q

What are two methods of making R-Hals?

A

1.Alkene + H-Hal ——-> R-Hal 2.R-OH + H-Hal ———–> R-Hal + H2O

164
Q

How do you make Alkenes from R-Hals?

A

R-Hal + Na/KOH ———> Alkenes + salt + H2O Dissolved In ethanol at high temperatures with High conc of the Na/KOH 2ary or 3ary R-Hals are preferred.

165
Q

How do you make Alcohols from R-Hals?

A

R-Hal + Na/KOH ———> Alcohol + salt Dissolved in water at low temperatures with low concentrations of Na/KOH. 1ary or 2ary R-Hal prefered.

166
Q

How do you make amines from R-Hals?

A

R-Hal + NH3 ——–> R-NH2?

167
Q

How can you test for which Hal is on your R-Hal?

A

R-Hal + Ag+ –> 1.Agcl - Wht ppt(sol In NH3) Very Slow 2.AgBr - Pale Cream ppt(Semi-sol) Slow 3.AgI - Yellow ppt(insoluble) Fast

168
Q

How can you manufacture Grignards Reagent?

A

R-Hal + Mg ————> Grignards Reagents: Magnisium metal with trace of iodine. Usually requires cooling. In the presence of ethoxyethane

169
Q

How can you make pure Alkanes with Grignards reagent?

A

R-MgHal + H2O —–> R + Mg(OH)Hal

170
Q

How can you produce a carbonyl From Grignards reagent?

A

R-MgHal + CO2 ——> RCOMgHal + H2O -> RCOOH

171
Q

How can you produce Alcohols from Grignards Reagents?

A

R-MgHal 1.+ methanal -> R-OMgHal + HCl -> R-OH 2.+ ethanal -> 2ary R-OH 3.+ Ketone -> 3ary R-OH

172
Q

How Is ethanol Produced Industrially?

A

Ethene + H20(g) —> Ethanol (At 300 C, 60-70 atm and with a phosphurous (v) acid catalyst)

173
Q

What are the conditions at which LDPE is produced? What are its uses?

A

T: 200 C, P 2000Atm O2 Impurity Uses: for plastic bags

174
Q

What are the conditions at which HDPE is produced? What are its uses?

A

T: 60 C P: A 2-5Atm Cat: Ziegler-Natta. Uses: milk bottles, plastic pipes and so on.

175
Q

What are the 3 orientations of PP and their uses?

A

Isotactic: Plastic Crates Atactic: Sealents, Adhesives and Roofing felt SyndioTactic: Medical tubing/bags ect.

176
Q

PCE - uses and full name

A

Poly(chloroethane) Guttering, plastic windows, cable insulation, sheet meterials footwear, clothing ect.

177
Q

PTFE - uses and full name

A

Poly(tetrafloroethane) - uses for wrapping foods and chemicals and have a non stick property used in the kitchen.

178
Q

What are the manufacturing conditions of Epoxyethane?

A

T: 250 C P:15atm Catalyst: Ag

179
Q

What are the Uses of Epoxyethane?

A

It is used to make long chain alcohols which can be used as: Anti-freeze materials, plasticizers non-ionic surfactants (detergants) and in the manufacture of polyesters.

180
Q

How can you produce Carboxilic acids?

A

R-COMgHal + H2O —-> R-COOH + Mg(OH)Hal (under acidic conditions)

181
Q

How can you produce Nitriles From R-Hals?

A

R-hal + KCN -> R-CN + KHal Reagents: Potatsium Cyanide dissolved in aquous ethanol. Conditions: heat under reflux. Doesn’t work with 3ary alkanes

182
Q

How can you produce amines from R-Hals?

A

R-Hal + 2NH3 -> R-NH2 + NH4Hal Reagents ammonia in ethanolic solution

183
Q

What is the equation for Fischer esterification?

A

R-OH + R-COO —-> Ester Catalyst: H2SO4

184
Q

What are acid anhydrides?

A

Two carboxlyic acids joint by the same oxygen.

185
Q

What is the Friedal-crafts reaction?

A

Electrophillic addition of aromatic rings.

186
Q

E.N of the Halogen UP: Strength of the H-hal Bond?

A

Strength of the H-hal bond UP

187
Q

Examples of nucloephiles

A

O:Water, Hydroxide, N:Azides Cyanide and Ammonia, Metal Halides,S: Sulfer Thiols.

188
Q

Examples of electrophiles

A

H+, NO+, HCl, aklyl halides, acyl halides, Carbonyl compounds.

189
Q

What is the Friedal-crafts reaction?

A

Electrophillic addition of aromatic rings.

190
Q

E.N of the Halogen UP: Strength of the H-hal Bond?

A

Strength of the H-hal bond UP

191
Q

Examples of nucloephiles

A

O:Water, Hydroxide, N:Azides Cyanide and Ammonia, Metal Halides,S: Sulfer Thiols.

192
Q

Examples of electrophiles

A

H+, NO+, HCl, aklyl halides, acyl halides, Carbonyl compounds.

193
Q

General formula for alkynes

A

CnH2n-2

194
Q

General formula for alkenes

A

CnH2n

195
Q

General formula for alkanes

A

CnH2n+2

196
Q

CaC2 + 2H2O ->

A

->Ca(OH)2 + C2H2 (ethyne/acetylene)

197
Q

Preparing ethyne

A

Water added to calcium carbide.

198
Q

Preparing ethene in lab

A

Dehydrate ethanol with concentrated H2SO4 (gives poor yield)

199
Q

Preparing ethene by cracking

A

Cracking saturated hydrocarbons via steam cracking naptha compounds (C4-C12)

200
Q

Properties alkenes /alkynes

A

Non polar, insoluble in water, low M.p/B.p but increase with size

201
Q

Sustitution

A

Alkanes with halogens, halogen atoms swap with hydrogen, hydrogen halide gas as a product, requires UV light

202
Q

C2H6 + Br2 -(UV)>

A

->C2H5Br + HBr

203
Q

Complete combustion of alkanes

A

CO2+H2O produced

204
Q

Incomplete combustion

A

Produce CO and/ or C (soot) instead of CO2

205
Q

Properties of alkanes

A

Single covalent bonds, Undergo combustion and substituion reactions, nonpolar(insoluble in water) Low MP/BP (increases with size), Less dense than water(float)

206
Q

Isomer

A

Different form of same molecular formula with a different structural formula

207
Q

Meth-

A

1 carbon

208
Q

Eth-

A

2 carbons

209
Q

Prop-

A

3 carbons

210
Q

But-

A

4 carbons

211
Q

CH2=CH2 + H2O -(dil. H2SO4/H3PO4)->

A

->CH3-CH2-OH

212
Q

Functional group

A

The specific arrangement of atoms and/or bonds responsible for the main physical +chemical properties

213
Q

Homologous series

A

Family of hydrocarbons with same functional group. Similar chemical + physical properties

214
Q

Hydration

A

Adding water to alkene, forms alcohols

215
Q

Halogenation

A

Adding a halogen to alkene, forms halogenoalkanes

216
Q

Testing for unsaturation

A

Bromine water, decolourises from orange/brown to colourless

217
Q

Hydrogenation

A

Adding hydrogen to an alkene, forms an alkane

218
Q

CH2=CH2 + H2 -(nickel/platinum)->

A

->CH3-CH3

219
Q

CH2=CH2 + Br2 ->

A

CH2BrCH2Br