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154 Cards in this Set
- Front
- Back
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What are the %s and %p characteristics in a sp hybridized orbital?
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50% and 50%
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What is the bond angle of an sp hybridized orbital?
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180 degrees
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What are the %s and %p characteristics in a sp^2 hybridized orbital?
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33%s and 66%p
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What is the bond angle of a sp^2 hybridized orbital?
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120 degrees
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What is the geometric configuration of associated with a sp^2 hybridized orbital?
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trigonal planar
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What are the %s and %p characteristics of a sp^3 hybridized orbital?
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25%s and 75%p
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What is the bond angle made by a sp^3 hybridized orbital?
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109.5 degrees
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What is the hydrogen deficiency of C6H12O?
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1
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What is the hydrogen deficiency of C3H6Br2
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0
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What is the hydrogen deficiency of C4H6N2
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3
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Constitutional isomerism
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Same molecular formula, different atomic connectivity
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How many constitutional isomers does butane have?
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2
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How many constitutional isomers does pentane have?
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3
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How many constitutional isomers does hexane have?
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5
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How many constitutional isomers does heptane have?
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9
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How many constitutional isomers does octane have?
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18
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How many constitutional isomers does nonane have?
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35
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Conformational isomers
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Same molecular formula, same connectivity, different orientation by rotation
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What are the two staggered conformations?
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Anti and Gauche
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How many degrees apart are the largest constituents in a gauche conformation?
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60 degrees
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How would one increase the stability of a gauche conformation without rotating any of the bonds?
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make hydrogen bonding possible
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What caused the high energy seen in an eclipsed conformation?
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sterric hindrance and electronic repulsion
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Why are larger groups better in the equatorial position of a cycloalkane?
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There is no 1-3 diaxial interaction
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List all of the stereoisomers.
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enantiomers, diastereomers, epimers , anomers, meso compounds, geometric isomers
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Stereoisomers
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same molecular formula, same connectivity, different spatial arrangement
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Diastereomers
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nonsuperimposable non-mirror images
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epimers
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differ around a single chiral center
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anomers
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epimers that form as a result of ring closure
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Which way to meso compounds rotate plane-polarized light?
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they do not rotate light
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geometric isomers
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diastereomers that differ about a ring or double bond (i.e. Z and E)
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Is CH3CH2CH2CH2CH3 a gas, liquid, or solid at room temperature?
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it is a liquid
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Is CH3CH2CH3 a gas, solid, or liquid at room temperature?
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Gas
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Which has a lower melting point: CH3CH2CH2CH2CH3 or CH3CH2CH2CH3
| CH3 |
CH3CH2CH2CH3
| CH3 |
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Which is more soluble: octane or propane?
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propane
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Which is the most stable Carbanion: Primary, secondary, tertiary, or methyl?
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methyl
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When you increase the stability of the conjugate base of an acid the ? acidic it becomes.
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less
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List all the major acids from most acidic to least
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HI>H2SO4>HBr>HCl>H3O+>HSO4->HF>CH3COOH>H2CO3>H2S>NH4+>HCN>HCO3->H2O>CH3OH>H2>CH3C=CH>NH3>CH3CH=CH2>CH3CH2CH3
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Do electron donating or withdrawing groups stabilize carbanions?
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Electron withdrawing groups
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Which cycloalkane is the most reactive: cyclobutane, cyclohexane, or cyclopentane?
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cyclobutane
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The propagation step in radical halogenation results in inversion or racemization?
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Racemization
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Name the three ways that free radical halogenation can be terminated.
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1. Halogen radical forms diatomic halogen
2. Alkane radical forms alkane 3. Haloalkane is formed |
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Which is more selective Br or Cl?
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Br
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Which results in a more exothermic free radical halogenation reaction: Br or Cl?
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Cl
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Are Nucleophiles good Lewis Bases or good Lewis Acids?
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Good Lewis Bases
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The stronger the base, the better or worse the nucleophile?
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Better
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Nucleophilicity increases _________ a group in the periodic table due to ____________.
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down; polarizability
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Nucleophilicity increases moving __________ across a period of the periodic table due to less ___________.
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left; electronegativity
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which is a better electrophile and why: BF3 or CCl4?
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BF3 due to the incomplete octet
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What are usually the substrates in SN2 reactions?
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Electrophilic alkyl halides
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Does Inversion or Racemization occur as a result of an SN2 reaction.
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Inversion
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An SN2 reaction has a ___________ transition state.
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pentavalent
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SN2 reactions are favored by aprotic or protic solvents?
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aprotic
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List the following alkanes in order of increasing reactivity in SN2 reactions: methyl, secondary, primary, tertiary.
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Tertiary<Secondary<Primary<Methyl
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SN2 reactions are favored by bulky or non-bulky nucleophiles?
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non-bulky
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Do SN1 reactions result in racemization or inversion?
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Racemization
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What is the rate determining step of a SN1 reaction?
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When the leaving group leaves
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SN1 reactions are favored by what kind of solvent?
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protic
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Why are SN1 reactions favored by protic solvents?
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1. stabilizes carbocation
2. solvates leaving group |
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SN1 reactions are favored by what kind of nucleophiles?
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non-basic weak nucleophile
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Does the solvent behave as a nucleophile or electrophile in SN1 reactions?
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nucleophile
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What is required for an ether to undergo a SN1 reaction?
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A strong acid
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Amines participate as nucleophiles or electrophiles in SN1 or SN2 reactions?
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Nucleophiles in SN2 reactions
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List the following alkanes in increasing order of reactivity for an E1 reaction: secondary, tertiary, primary, methyl.
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Methyl<primary<secondary<tertiary
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Which is the favored product of an E1 reaction: the trans or cis isomer?
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trans
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The more highly ____________ alkene is favored as the product of an E1 reaction.
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substituted
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What kind of reaction is a dehydration reaction?
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E1
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What kind of solvent is an E1 reaction favored by?
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Protic
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E1 is favored over SN1 by a ______ base and ________ temperature.
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weak; high
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What kinds of alkanes are the substrates of E2 reactions?
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Alkyl halides
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What is the order of reactivity for alkanes in an E2 reaction?
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3>2>1>methyl
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Small bases favor _______ substituted alkene in an E2 reaction.
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least
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_______ bases favor most substituted alkene in an E2 reaction.
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bulky
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E2 reactions are favored by ________solvents.
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aprotic
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Are E2 reactions favored by weak or strong bases?
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strong
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Are E2 reactions favored by high or low temperatures?
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High
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What is the effect of INTRAmolecular H-bonding on melting and boiling point?
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It decreases both
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Does intramolecular H-bonding increase or decrease acidity?
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decrease
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Do electron withdrawing group increase or decrease acidity?
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increase
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What reagents would you use to make an alkyl halide from an alcohol?
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Phosphorous trihalide, phosphorous trichloride, or thionyl chloride
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Adding HBr, HCl, or HI to an alkene is what type of reaction?
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electrophilic addition
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Electrophilic addition of HBr, HCl, or HI results in inversion or racemization?
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Racemization
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Does Electrophilic addition of a protic acid occur via the markovnikov mechanism?
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Yes
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What is the Markovnikov mechanism?
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Hydrogen add to the least substituted carbon of an alkene and the halide adds to the more substituted carbon
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What kind of reaction is acid catalyzed hydration and oxymercuration-demercuration?
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electrophilic addition
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Why is sulfuric acid used in acid catalyzed hydration?
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Its conjugate base in nonnucleophilic
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In the oxymercuration demercuration reaction, does the OH add to the more substituted or less substituted carbon?
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more substituted
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Does hydroboration follow markovnikov or antimarkovnikov?
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antimarkovnikov
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In hydroboration, do the H and OH add anti or syn to one another?
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syn
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The addition of dihalogens is __________ addition.
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electrophilic
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Does the addition of dihalogens occur via markovnikov or antimarkovnikov?
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antimarkovnikov
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Does the addition of dihalogens result in inversion or racemization?
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racemization
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In electrophilic addition of Br2, do the bromines add anti or syn to one another?
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anti
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Treating alkenes with peroxy acids will produce ________ diols.
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trans
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Treating alkenes with peroxy acids results in what kind of mixture?
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racemic
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Treatment with KMnO4 or OsO4 produces what kind of diol?
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cis
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Electrophilic addition of H2 with Ni, Pd, or Pt adds hydrogens syn or anti?
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syn
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Addition of H2 with a lindlar catalyst adds hydrogens cis or trans to one another?
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cis
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What reagent would you use to add Hydrogens anti to one another to an alkyne and make an alkene?
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Sodium in ammonia (NaNH2)
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For a structure to be cyclic, every atom must have an unhybridized ____ orbital.
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p
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For a structure to be cyclic, all p orbital must be ________ and possess Huckel's number _________.
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planar; 4n+2
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Order the following from most to least electron donating: OR, OH, NR2, NHC=O, R.
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NR2>OH>OR>NHC=O>R
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Are ring electron donating groups ortho, para, or meta directing?
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Ortho, para
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List these electron withdrawing groups in order of decreasing strength: NO2, NR3+, SO3H, OH-C=O, NH2-C=O, NH3+
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NR3+>NO2>SO3H>HO-C=O, NH2-C=O, NH3+
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PCC, CrO3, CrO4, Cr2O7, MnO4, and H2CrO4 are all used in the oxidation or reduction of __________?
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Oxidation; alcohols
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Which of these will NaBH4 NOT reduce: Aldehydes, Carboxylic acids, Esters, ketones
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Carboxylic acids and esters
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Which of these will LiAlH4 NOT reduce: Carboxylic acids, amids, ketones.
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LiAlH4 will reduce all of them
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Organometallic reagents are used as strong _________ or ___________.
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bases; nucleophiles
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What acts as the nucleophile in a gringard reagent?
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R-MgBr
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Is a protic or aprotic solvent used in a gringard reaction?
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aprotic
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What kind of ion forms as a result of a gringard reaction?
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alkoxide
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Imine formation occurs in a weakly _________ buffer solution.
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acidic
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Protonating the oxygen in an imine formation makes the carbon more nucleophilic or electrophilic?
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electrophilic
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In a crossed aldol condensation, the carbonyl with no acidic protons acts as the electrophile or nucleophile?
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electrophile
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What kind of reaction does a betahyroxyaldehyde undergo when heated?
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dehydration
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Conjugate addition at the beta carbon is a _,_ addition.
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1,4
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Beta keto acids undergo ____________ and a loss of what gas?
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decarboxylation; CO2
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Order these carboxylic acid derivatives in order of increasing reactivity: Ester, acid anhydrides, amides, acid halides.
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acid halides>acid anhydrides>esters>amides
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What kind of reaction is esterification?
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Dehydration
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Acid catalyzed ester hydrolysis results in what?
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carboxylic acid
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Base mediated ester hydrolysis results in what?
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carboxylate ion
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Saponification of fats results in ____________ and __________.
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Carboxylate salts and glycerol
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P4O10 and HCO2Na with acid halides or carboxylic acids results in what?
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acid anhydrides
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Liquid Liquid extraction
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Separates based on solubility
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Water extraction
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Removes polar substances
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What does a dilute acidic solution extract?
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Basic compounds
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A dilute basic solution converts _____ into anionic _____.
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acids; salts
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Is precipitation driven by a positive or negative ΔH?
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Negative
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Precipitation has a negative ΔH due to more stable ___________interactions.
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intermolecular
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In thin layer chromatography, do polar or nonpolar substances travel faster?
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nonpolar
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In thin layer chromatography, is the stationary phase polar or nonpolar?
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Polar
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How do you calculate Rf?
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distance traveled by substance/distance traveled by solvent
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In column chromatography, Which compound will travel slowest: Propane, hexane, or ethanol?
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ethanol
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In gas chromatography, will a gas with a VP of 10 or 20 emerge from the column first?
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20
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What is the difference between simple and fractional distillation?
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simple is used for substances with VERY different BP.
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Fractional distillation is a process of __________and___________.
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vaporization and condensation
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Will fractional distillation purify the substance with the lower or higher BP?
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lower
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Which constituent has an IR frequency of 1700cm^-1?
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Carbonyl
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Alkynes have an IR frequency of what?
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2200cm^-1
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Aliphatic C-H bonds have an IR frequency of what?
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2700-3300cm^-1
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Amine bonds have IR frequencies between 2500 and _______.
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3200
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Which constituent has an IR absorption of 3200-3600?
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OH
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Aromatic C-H bonds absorb at IR frequencies slightly greater than_______.
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3000
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What shields the protons from a device magnetic field?
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electron magnetic field
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What does a Proton NMR chemical shift to the right suggest?
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Increased shielding
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Increasing the acidity ________ the shielding and shifts spectra to the _____.
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decreases; left
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Oxidation of a compound shifts NMR spectra to the right or left?
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left
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When does splitting occur?
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when protons interact with nonequivalent protons.
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How do you increase the height of a Carbon NMR peak?
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add hydrogens
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Is the amine group on an L amino acid on the left or right side?
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Left
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What is the approximate pKa of carboxyl groups?
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2
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What does Base/Acid equal when the pH equals the pKa of an acid?
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1
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On which side do L carbohydrates have the OH group?
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left
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Are animal carbohydrates derived from D or L glyceraldehyde?
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D
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The backbone of a polypeptide is structured as: N-?-C-?-?-C
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C; N; C
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