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OAT > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

1
Q

(T/F) A pi bond can exist without a sigma bond

A

False, a pi bond cannot exist independently of a sigma bond

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2
Q

Which type of bond (pi or sigma) is stronger?

A

A sigma bond is generally stronger than a pi bond

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3
Q

What is the hybridization of the carbon atom in CH4? What are the bond angles?

A

sp3, 109.5º

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4
Q

What is the bond angle between sp hybridized atoms?

A

180º

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5
Q

What is the bond angel between sp2 hybridized atoms?

A

120º

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6
Q

What is the general formula of a noncyclic alkane?

A

The general formula of an alkane is CnH2n+2

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7
Q

How many other carbons are 1’, 2’, 3’, and 4’ carbons bonded to?

A

1, 2, 3, and 4 other carbons respectively

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8
Q

How does increasing molecular weight affect the boiling point and melting point of an alkane

A

Increased molecular weight results in increased boiling and melting points

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9
Q

How does increased branching affect the boiling boil of an alkane

A

Increased branching lowers the bowling point

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10
Q

What are the three steps of a halogenation reaction?

A

Initiation, Propagation, and Termination

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11
Q

What does X2 –> (hv or ^) 2X• represent?

A

Initiation

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12
Q

what does 2X2• —> X2 represent?

A

Termination

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13
Q

What does R• + X2 –> RX + X• represent?

A

Propagation

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14
Q

What does X• + R• –> XR represent?

A

Termination

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15
Q

What does X• + RH –> HX + R• represent?

A

Propagation

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16
Q

What does 2R• –> R2 represent?

A

Termination

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17
Q

What is the order of free radical stability?

A

3º > 2º > 1º > methyl

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18
Q

What type of reaction involves breaking down large alkanes into smaller ones?

A

Prolysis or “cracking” uses heat to break down large alkanes into smaller ones

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19
Q

What are the products of the complete combustion of an alkane?

A

The complete combustion of an alkane produces: CO2, H2O, and heat

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20
Q

Is a nucleophile electron rich or electron poor?

A

A nucleophile is electron rich

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21
Q

All else being equal, how does basicity affect he strength of a nucleophile?

A

The stronger the base, the stronger the nucleophile

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22
Q

How many steps are involved in an SN1 reaction? What are they?

A

There are two steps in an SN1 reaction.

  1. the molecule dissociates into a carbocation and a leaving group
  2. the nucleophile combines with the carbocation
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23
Q

What is the order of carbocation stability?

A

3º > 2º > 1º > methyl

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24
Q

Which step in an SN1 reaction is the rate determing step?

A

The first step, the formation of the carbocation, is the rate determing step

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25
Q

(T/F) The rate of an SN1 reaction is dependent on the concentration of the nucleophile

A

False, the rate is only dependent on the concentration of the original molecule

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26
Q

How can SN1 reaction rate be increased?

A
  1. Stablilize the carbocation by increasing substitution and using a highly polar solvent
  2. Use a better leaving group (weak base)
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27
Q

How does basicity affect the nature of a leaving group?

A

The weaker the base, the better the leaving group

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28
Q

How many steps are involved in an SN2 reaction?

A

SN2 reactions have one step

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29
Q

Is the rate of an SN2 reaction dependent on the concentration

A

The SN2 reaction rate is dependent on the concentration of both the substrate and the nucleophile

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30
Q

(T/F) SN1 reactions involving a chiral substrate produce an optically active mixture

A

False, a racemic mixture results during SN1 reactions with an optically active reactant

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31
Q

(T/F) SN2 reactions involving a chiral substrate result in an inverted, optically active product

A

True

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32
Q

Which type of reaction is favored (SN1 or SN2) given the folowing conditions:

  1. Polar protic solvent
  2. Polar aprotic solvent
  3. Methyl or 1º alkyl halide
  4. 3º alkyl halide
A
  1. Polar protic solvents favor SN1
  2. Polar aprotic favor SN2
  3. Methyl or 1º alkyl halides favor SN2
  4. 3º alkyl halides favor SN1
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33
Q

Which form of an alkene has a higher melting point (cis or trans)?

A

trans due to symmetry

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34
Q

Which form of an alkene has a higher boiling point (cis or trans)?

A

cis

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35
Q

How many steps are there in an E1 elimination reaction?

A

There are 2 steps

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36
Q

How many steps are there in an E2 elimination reaction?

A

1 step

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37
Q

(T/F) E1 and SN1 reactions are driven by the same factors (polar solvent, good leaving groups, highly branched chains)?

A

True

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38
Q

(T/F) In the case of E2, the least substituted double bond is usually formed preferentially

A

False, E2 reactions favor the formation of highly substituted double bonds

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39
Q

What is Markovnikov’s rule?

A

Protons will add to the less substituted carbon of a double bond to create a more stable carbocation intermediate

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40
Q

Would the electrophilic addition of Br2 to an alkene result in syn or anti addition?

A

The Br2 would undergo anti addition

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41
Q

(T/F) The reduction of an alkyne on a metal surface (Pd) results in a cis alkene

A

False. It results in an alkane

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42
Q

(T/F) The reduction of an alyne in Na and NH3 produces a trans alkene

A

True

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43
Q

Does the electrophilic addition of HBr to an alkyne follow Markovnikov’s rule?

A

Yes, electrophilic addition of HBr to an alkyne or an alkene follows Markovnikov’s rule

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44
Q

Does the free radical addition of HBr to an alkyne follow Markovnikov’s rule?

A

No, free radical addition of HBr to an alkyne or an alkene does not follow Markovnikov’s rule

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45
Q

What is an aromatic compound?

A

A aromatic compound is defined as any unusually stable ring system. Aromatic compounds are cyclic, conjugated polyenes that follow Hückel’s rule

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46
Q

What is an aliphatic compound?

A

An aliphatic compound is any non-aromatic compound

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47
Q

What is Hückel’s rule?

A

Hückel’s rule states that an aromatic compund has (4n+2)π electrons, where n is an nonnegative integer

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48
Q

What is antiaromatic compound?

A

An antiaromatic compound is a cyclic conjugated polyene with 4n electrons

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49
Q

What is the difference between a phenyl and a benzyl group?

A

A benzene ring acting as a substituent is call a phenyl group (-C6H5). A tolune molecule substituted at the methyl position is called a benzyl- group (-CH2C6H5)

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50
Q

Do electron donating groups activate or deactivate an aromatic ring?

A

Electron donating groups activate a ring

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51
Q

How do electron withdrawing groups affect the reactivity of an aromatic ring?

A

Electron withdrawing groups deactivate a ring

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52
Q

Is COOH activating/ deactivating and ortho/para or meta directing?

A

Deactivating / meta

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53
Q

Is NR2 activating/ deactivating and ortho/para or meta directing?

A

Activating/ ortho-para

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54
Q

Is NH2 activating/ deactivating and ortho/para or meta directing?

A

Activating / ortho-para

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55
Q

Is NO2 activating/ deactivating and ortho/para or meta directing?

A

Deactivating / meta

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56
Q

Are F, Cl, Br, I activating/ deactivating and ortho/para or meta directing?

A

Deactivating / ortho-para

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57
Q

Is COOR activating/ deactivating and ortho/para or meta directing?

A

Deactivating / meta

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58
Q

Is OR activating/ deactivating and ortho/para or meta directing?

A

Activating / ortho-para

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59
Q

Is SO3H activating/ deactivating and ortho/para or meta directing?

A

Deactivating / meta

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60
Q

Is OCOR activating/ deactivating and ortho/para or meta directing?

A

Activating / ortho-para

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61
Q

CH3 activating/ deactivating and ortho/para or meta directing?

A

Activating / ortho-para

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62
Q

(T/F) Activating compounds are always o-p directors?

A

True

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63
Q

(T/F) Deactivating compunds are always meta directors

A

False, halogens are deactivating and are o-p directing

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64
Q

Why do alcohols have a significantly higher boiling point than analogous alkanes?

A

Alcohols can hydrogen bond

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65
Q

(T/F) Phenols are less acidic than aliphatic alcohols

A

False, phenols are much more acidic than aliphatic alcohols

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66
Q

What are three types of reactions used to synthesize alcohols?

A

Addition, Substitution, and Reduction

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67
Q

Can a tertiary alcohol be easily oxidized?

A

No, tertiary alcohols cannot be oxidized without cleavage of a carbon-carbon bond

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68
Q

Can ethers hydrogen bond?

A

No, ethers do not hydrigen bond

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69
Q

(T/F) Straight chain ethers can be cleaved under high temperature in the presence of HBr or HI

A

True

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70
Q

How does the boiling point of an aldehyde (or ketone) compare with its analogous alkane? Alcohol?

A

The boiling point of an aldehyde is higher than that of the corresponding alkane but lower than that of the corresponding alcohol

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71
Q

How is a ketone or an aldehyde from an alcohol?

A

Oxidizing an alcohol will produce the corresponding ketone or aldehyde (ie by using PCC or Na2Cr2O7)

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72
Q

How do you produce a ketone or aldehyde from an alkene?

A

Ozonolysis of an alkene will produce corresponding ketons or aldehydes as cleavage products

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73
Q

Which protons relative to a carbonyl group are acidic?

A

Alpha protons relative to a carbonyl group are slightly acidic

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74
Q

What happens when aldehydes or ketons react with water?

A

Aldehydes adn ketons react with water to form gemdiols

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75
Q

(T/F) A reaction in which two molecules combine with the loss of a water molecule is a condensation reaction

A

True

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76
Q

What would be the product when acetaldehyde is reacted with dilute NaOH?

A

aldol

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77
Q

What is the name of the reaction when acetaldehyde is reacted with dilute NaOH?

A

Aldol condensation

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78
Q

What are the common names for the first three straight chain carboxylic acids?

A

The first three carboxylic acids are: formic acid, acetic acid, and propionic acid

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79
Q

(T/F) Alcohols have higher boling points than carboxylic acids

A

False, carboxylic acids have higher boiling points than corresponding alcohols

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80
Q

How do electron withdrawing groups (-Cl, -NO2) attached to the alpha carbon affect the acidity of the carboxylic acid?

A

Electron withdrawing groups increase acidity

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81
Q

How do electron donating groups (-NH2, -OCH3) attached to the alpha carbon affect the acidity og a carboxylic acid?

A

Electron donating groups decrease acidity

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82
Q

What type of alcohol (1º, 2º, 3º) can be oxidized to carboxylic acid?

A

1º alcohols can be oxidized to carboxylic acids, however 2º and 3º alcohol cannot

83
Q

What is a micelle? Is the interior hydrophobic or hydrophillic?

A

When placed in an aqueous solution, soap molecules arrange themselves into spherical structures called micelles. The soap molecules arrange themselves such that their polar heads face outward and their nonpolar chains face inward

84
Q

Would you have to oxidize or reduce a carboxylic acid to prepare an alcohol?

A

Reduction of a carboxylic acid forms an alcohol

85
Q

(T/F) Acid chlorides are very reactive

86
Q

How do electron donating groups affect the acidity of benzoic acid?

A

Electron donating groups reduce the acidity of benzoic acid

87
Q

How do electron withdrawing groups affect the acidity of benzoic acid?

A

Electron withdrawing groups increase the acidity benzoic acid

88
Q

(T/F) Anhydrides react under the same conditions as acid chlorides

89
Q

What is the product of the hydrolysis of an amide under acidic conditions?

A

The hydrolysis of an amide under acidic conditions will produce a carboxylic acid

90
Q

What are the products for the hydrolysis of an ester?

A

The products are a carboxylic acid and an alcohol

91
Q

What is saponification?

A

Saponification is the process whereby fats are hydrolyzed, under basic conditions, to produce soaps

92
Q

What is transesterification?

A

C-CO-OR’ + R”OH <-> C-CO-OR” + R’OH

93
Q

(T/F) A glycerol molecule attached to two carboxylic acids and one phosphoric acid is a phospholipid

94
Q

Name: CH3CH2NH2

A

Ethylamine (common) or ethanamine (IUPAC)

95
Q

Name: CH3CH2CH2CH2N(CH3)2

A

N,N-dimethylbutylamine (common) or N,N-dimethylbutanamine (IUPAC)

96
Q

How many alkyl groups are in a tertiary (3º) amine?

A

A 3º amine has 3 alkyl groups attached to the nitrogen

97
Q

What is a quaternary ammonium compound?

A

A 4º ammonium coupound is a ntrogen atom attacked to 4 alkyl gorups. The nitrogen is positively charded and, therefore, the compound exists as a salt

98
Q

(T/F) An imine is a compound with a carbon-nitrogen double bond

99
Q

Which types of amines can form hydrogen bonds (1º, 2º, 3º)

A

1º and 2º amines can form hydrogen bonds

100
Q

(T/F) Axial hydrogens are parallel to the ring

A

False, axial hydrogen are perpendicular to the ring

101
Q

(T/F) Bulky groups prefer the equatorial position over the axial group

102
Q

what are geometric isomers?

A

Geometric isomers are molecules that differ with respect to the spatial relationship of substituents around a double bond

103
Q

What is a chiral molecule?

A

A chiral molecule is a molecule that is not superimposable upon its mirror image

104
Q

What are enantiomers?

A

Enantiomers are chiral molecules that are non-superimposable mirror images of each other

105
Q

(T/F) Achiral molecules are optically active

A

False, achiral molecules are optically inactive

106
Q

What is a dextrorotatory (+) compound?

A

A dextrorotatory compound rotates polarized light to the right (clockwise)

107
Q

What type of chemical bond involves the sharing of electrons?

A

Covalent bonds involve the sharing of electrons

108
Q

What type of chemical bond involves the sharing of electrons?

A

Covalent bonds

109
Q

What type of chemical bond involves the transfer of electrons?

A

Ionic bonds

110
Q

What orbital has a spherical shape?

A

”s” orbitals are spherically shaped

111
Q

What orbital has a bi-lobed shape?

A

“p” orbitals are bi-lobed

112
Q

What are the prefixes of the first 12 alkanes?

A

Meth, Eth, Prop, But, Pent, Hex, Hept, Oct, Non, Dec, Undec, Dodec

113
Q

What are the 5 steps used to name alkanes according to IUPAC rules?

A
  1. Find the longest chain
  2. Number the chain so that the lowest set of numbers is obtained for the substituents
  3. Name and alphabetize the subst.
  4. Assign a number to each subst.
  5. Complete the name
114
Q

What are the 5 steps used to name alkenes according to IUPAC rules?

A
  1. Find the longest chain containing the double bond
  2. Number the chain so that the double cond receives the lowest possible number
  3. Name and alphabetize subst.
  4. Specifiy the configurational isomer
  5. Name the compound
115
Q

What is the common name for ethyne?

A

Ethyne is commonly known as acetylene

116
Q

In the case of an”en-ol” which carbon receives the lowest number?

A

The carbon attached to the alcohol group is assigned the lowest number

117
Q

What is a diol?

A

A diol is a molecule with two hydroxyl (OH) groups

118
Q

(T/F) An aldehyde has a carbonyl group somewhere in the middle of the carbon chain

A

False. In an aldehyde, the carbonyl group is at the end of the carbon chain

119
Q

(T/F) A ketone has the carbonyl group at one end of the carbon chain

A

False. In a ketone, the carbonyl group is somewhere in the middle of the carbon chain

120
Q

In the case of an “en-one” which carbon receives the lowest number?

A

The carbonyl carbon receives the lowest number

121
Q

What type of compound does a -COOH group denote?

A

The COOH group denotes a carboxylic acid

122
Q

What are the common names for the following:

  1. methanoic acid
  2. ethanoic acid
  3. propanoic acid
A
  1. formic acid
  2. acetic acid
  3. propionic acid
123
Q

Name the functional group: RSN

124
Q

Name the functional group: R2S

125
Q

Name the functional group: RNO2

126
Q

Name the functional group: RN3

127
Q

Name the functional group: RN2+

128
Q

Name the prefix and suffix: Carboxylic acid

A

carboxy- / -oic acid

129
Q

Name the prefix and suffix: Ester

A

alkoxycarbonyl- / -oate

130
Q

Name the prefix and suffix: Acyl Halide

A

halocarbonyl- / -oyl halide

131
Q

Name the prefix and suffix: Amide

A

amido- / -amide

132
Q

Name the prefix and suffix: Nitrile

A

cyano- / -nitrile

133
Q

Name the prefix and suffix: Aldehyde

A

oxo- / -al

134
Q

Name the prefix and suffix: Ketone

A

oxo- / -one

135
Q

Name the prefix and suffix: Alcohol

A

hydroxy- / -ol

136
Q

Name the prefix and suffix: Thiol

A

sulfhydryl- / -thiol

137
Q

Name the prefix and suffix: Amine

A

amino- / -amine

138
Q

Name the prefix and suffix: Ether

A

alkoxy- / -ether

139
Q

Name the prefix and suffix: Sulfide

A

alkylthio- / -sulfide

140
Q

Name the prefix and suffix: Nitro

A

nitro- / ~

141
Q

Name the prefix and suffix: Azide

A

azido- / -azide

142
Q

Name the prefix and suffix: Diazo

A

diazo- / ~

143
Q

What is a structural isomer?

A

Structural isomers have the same chemcial formulas, but different atomic connectivity

144
Q

What is a stereoisomer?

A

Stereoisimers are compunds that differ only in respect to the spatial arrangement of their atoms

145
Q

Order the following conformation of n-butane according to energy levels (low to high): gauche, anti, eclipsed, totally eclipsed

A

Anti, gauche, totally eclipsed

146
Q

What are the three cyclic hexam conformers in order of energy levels (low to high)

A

Chair, twisted, boat

147
Q

What is a levorotatory (-) compound?

A

A levorotatory compound rotates polarized light to the left (counterclockwise)

148
Q

What is a recemic mixture?

A

A racemic mixture contains equal amounts of both enantiomers

149
Q

How many stereoisomers are possible for a molecule with four chiral centers?

A

A racemic mixture contains equal amounts of both enantiomers

150
Q

How many stereoisomers are possible for a molecule with four chiral centers?

151
Q

What are diastereomers?

A

Diastereomers are stereoisomers that are not mirror images of each other

152
Q

What types of molecules are optically active?

A

Chiral molecules

153
Q

What is a meso compound?

A

A meso compound is a molecule that possess stereocenters but has a plane of symmetry. It is achiral and therefore optically inactive

154
Q

(T/F) All single bonds are sigma bonds?

155
Q

What type of bond results when two p orbitals overlap?

A

Two overlapping p orbitals for a pi bond

156
Q

What are the components of a double bond

A

A double bond is composed of 1 sigma and 1 pi bond

157
Q

What are the compondents of a triple bond?

A

A triple bond is composed of 1 sigma and 2 pi bonds

158
Q

Which purification technique involves a solif turning directly into a gas?

A

Sublimation

159
Q

What separation technique makes use of two immiscible solvents?

A

Extraction

160
Q

What seperation technique can be used to isolate a solid from a liquid?

A

Filtration

161
Q

(T/F) Recrystallization is a process in which impure crystals are dissolved in hot solvent and then recrystallize as pure crystals as the solvent cools

162
Q

Which separation technique can be used to separate a mixture of particiles with different densities and masses?

A

Centrifugation

163
Q

Which separation technique takes advantage of a solution containing two or more compunds with different boiling points?

A

Distillation

164
Q

(T/F) Vacuum distillation can be used to seperate liquids with very high boiling points

165
Q

Which separation technique separate compounds based upon their different affinities for a medium?

A

Chromatogrpahy

166
Q

What is the Rf value in thin layer chromatography (TLC)

A

The Rf value is the distance a compound travels divided by the distance the solvent travels

167
Q

Would a compound with a high Rf value be near the top or near the bottom of a TLC plate?

A

A compound with a high Rf value would be near the top of a TLC plate

168
Q

Which separation technique uses an electric field?

A

Electrophoresis

169
Q

SDS-polyacrylamide gel electrophoresis sepatates proteins based on what factor?

A

Based on their masses

170
Q

(T/F) Agarose gel electrophoresis is used to separate fragments of nucleic acid

171
Q

What type of spectroscopy is useful for identifying functional groups?

A

IR is useful. NMR has limited utility in this area.

172
Q

Do symmetrical stretches exhibit an IR absorption signal?

173
Q

(T/F) NMR spectroscopy can be used to identify distinct 1H protons in a molecule

174
Q

How many different NMR peaks (doublets, triplets, etc) would appear if the molecule being analyzed were:

Ethane

Propane

1,3-dichloropropane

A

Ethane - 1 singlet

Propane - 1 septet (7) and 1 triplet

1,3-dichloropropane - 1 quintent and 1 triplet

175
Q

How many different types of equivalent protons are there in 1-bromo-2-chloropropane?

A

There are three different types of equivalent protons

176
Q

What type of spectroscopy is ideal for the study of conjugated olefins?

A

UV-vis spectroscopy is ideal

177
Q

What type of spectroscopy can determine the molecular weight of a compound?

A

Mass spectroscopy determines the molecular weight of a compound

178
Q

What is the general formula for a carbohydrate?

179
Q

(T/F) Monosaccharides undergo many of the same reactions as alcohols

180
Q

What is the general formula for calculating the maximum number of possible stereoisomers of a molecule?

A

The general formula is 2n where n = number of chiral centers

181
Q

(T/F) When converting a Fischer Projection to a Haworth (ring) Projection, groups on the right side of a Fischer Projection will be pointing upward

A

False, groups on the right side of a Fischer Projection end up pointing downward in a Haworth Projection

182
Q

What monosaccharides make up a molecule of maltose?

A

Maltose is composed of two molecules of glucose

183
Q

Does cellulose contain ß-1,4 glycosidic bonds or a-1,4 glycosidic bonds

A

Cellulose contains ß-1,4 glycosidic bonds

184
Q

Do starch and glycogen contain ß-1,4 glycosidic bonds of a-1,4 glycosidic bonds?

A

Starch and glycogen contain a-1,4 glycosidic bonds

185
Q

What is mutarotation?

A

Mutarotation is the spontaneous change of configuration about C1 that occurs when monosaccarides are exposed to water

186
Q

(T/F) Glucose is an aldohexose

187
Q

(T/F) Fructose is an aldopentose

A

False, fructose is a ketohexose

188
Q

What is a reducing sugar?

A

A reducing sugar is any monosaccharide with a hemi-acetal ring

189
Q

(T/F) The alpha carbon is chiral in all amino acids

A

False, glycine’s alpha carbon has 2 hydrogens and is therefore not chiral

190
Q

What is a zwitterion?

A

A zwitterion is a species with both a positive and a negative charge

191
Q

Define amphoteric

A

An amphoteric species can act as either a base or an acid

192
Q

In what direction will an amino acid with a neutral side chain move during electrophoresis at pH 4:

  1. If the pI of the amino acid is 7?
  2. If the pI of the amino acid is 3?
  3. If the pI of the amino acid is 4?
A
  1. The amino acid will have a net positive charge and, therefore, move toward the cathode
  2. The amino acid will have a net negative charge and, therefore, move towards the anode
  3. The amino acid is at its isoelectric point and will not move
193
Q

(T/F) The buffering capacity of an amino acid is greatest at its isoelectric point

A

False, the buffering capacity of an amino acid is least at its isoelectric point. It is greatest at its two or more pKa’s

194
Q

Where are nonpolar amino acids usually found in a protein and why?

A

nonpolar amino acids are usually found in the interior of a protein because they are hydrophobic

195
Q

What is the net charge of a basic amino acid at physiological pH?

A

The net charge of a basic amno acid at physiological pH is positive

196
Q

What type of bond joins amino acids?

A

a peptide bond joins amino acids together

197
Q

Define the primary structure of a protein

A

Primary structure refers to the sequence of amino acids

198
Q

Define secondary structure

A

Secondary structure refers to hydrogen bond interactions within the protein

199
Q

What are the two most common types of secondary structure?

A

The two most common types of secondary structure are a-helix and ß-pleated sheet

200
Q

What are the two primary classifications (regarding tertiary structure) of proteins?

A

Fibrous and globular proteins

201
Q

Define quaternary structure

A

quarternary structure only exists in proteins with more than one polypeptide subunit. If refers to the way the subunits arrange themselves

202
Q

What is a conjugated protein?

A

A conjugated protein is a protein that derives part of its fucntion from a prosthetic group

203
Q

What happens when a protein denatures? What can cause a protein to denature?

A

A protein loses its three-dimensional shape when it denatures. Changes in temperature, pH, and solute concentration can cause denaturation

OAT (3 decks)

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