Final Exam Flashcard Answers

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question

Boiling Points:

  1. CH4
  2. NH3
  3. H2O
answer
  1. -162° C
  2. -33° C
  3. 100° C
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How many kcal/mole more stable is benzene due to resonance?
answer
36 kcal/mole
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How strong is the hydrogen bond?

 

answer
5-6 kcal/mole
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What are the bond strengths of:
  1. C=C (? + ?)
  2. C=C (? only)
  3. C—C 
  4. C—H
  5. H—H
answer
  1. 146 kcal/mole
  2. 63 kcal/mole
  3. 83 kcal/mole
  4. 99 kcal/mole
  5. 104 kcal/mole
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General formula for alkanes:
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CnH2n+2
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General formula for cycloalkanes:
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CnH2n
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R-Cl
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alkyl chloride
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R-OH
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alcohol
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[image]
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carbonyl - can be either:

  • aldehyde
  • ketone
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[image]
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aldehyde
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[image]
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ketone
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[image]
answer
formaldehyde
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[image]
answer
amide
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[image]
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carboxyl/carboxylic acid
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[image]
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ester/carboxylic acid ester
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[image]
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nitrile
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[image]
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secondary (2°) amine
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[image]
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ether
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Rotational energy barrier for C=N pi bond:
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?18 kcal/mole
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Rotational energy barrier O=O pi bond:
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?5 kcal/mole
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pKa of H2O:
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15.7
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pKa of hydronium ion (H3O+):
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-1.7
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pKa=?
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-log(Ka)
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Ka equation for following reaction of weak acid (HX):

 

HX + H2O - H3O+ + X-

answer

Ka = [H3O+] [X-] ? [HX]

 

or:

Ka = [H3O+]2 ? [HX]

 

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Electronegativities of following elements:

 

H          C          N          O          F

 

 

                        P           S          Cl

answer

H          C          N          O          F

2.2       2.5       3.0        3.5        4.0

 

                        P           S          Cl

                       2.2        2.5        3.0

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pKa of acetic acid: [image]
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4.7
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pKof ethanol: [image]
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?16
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pKa of chloroacetic acid: [image]
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?2.9
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pKa of methane:

 [image]

answer
50-60
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pKa of an alkene:

[image]

answer
?44
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pKa of a terminal alkyne:

 

R?C—H

answer
?25
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For EA, how many kcals/mole per order of magnitude?
answer
1.35 kcal/mole
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EA difference between eclipsed and staggered ethane:

[image]

answer
2.9 kcal/mole
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Difference in energy between gauche and anti-butane:

[image]

answer
?0.8 kcal/mole
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How much more stable is the chair confomer than the half-chair confomer of cyclohexane?

[image]

answer
?10.9 kcal/mole
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How much more stable is equitorial methyl-cyclohexane than axial-methylcyclohexane?

[image]

answer
?1.8 kcal/mole
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In what category do these belong? Name them:

[image]

answer

Bicyclic compounds

  1. bicyclo [4.3.0] nonane (fused)
  2. bicyclo [3.2.1] octane (bridged)
  3. bicyclo [3.2.2] nonane (bridged)
  4. bicyclo [3.3.1] nonane (bridged)
  5. bicyclo [4.2.0] octane (fused)
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Formula for number of possible enantiomers:

[image]

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2n where n=total centers of chirality
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[image]
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sulfydryl group/thiol
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Draw the intermediate of an SN2 reaction and indicate its hybridization state
answer

[image]

sp2 hybridized

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What are the relative rates of the following alkyl-halides for SN2 reactions?

  1. methyl halide (1°)
  2. ethyl halide (1°)
  3. isopropyl halide (2°)
  4. neopentyl halide (1° - special case)
  5. tertiary (3°) alkyl halide 
answer
  1. 30
  2. 1
  3. 0.03
  4. 10-5
  5. 0
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  1. ?G and
  2. Rate equation for reaction: 

 

CH3—Cl + -OH > CH3—OH + Cl-

answer
  1. -24 kcal/mol
  2. rate = [CH3Cl] [-OH]Ae?G/RT
question

Rank these oxygen containing compounds in order of decreasing nucleophilicity:

 

-OH, H2O, RO-, ROH, RCO2-

answer
RO->-OH>RCO2->ROH>H2O
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Rank these compounds in order of decreasing nucleophilicity:

 

HS-, I--OH, CN-

answer
HS->CN->I->-OH
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Rank these compounds in order of decreasing nucleophilicity:

 

CH3CO2-, CH3OH, CH3O-,CH3CO2H, CN-

answer
CN->CH3O->CH3CO2->CH3CO2H>CH3OH
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What is the resultant stereochemistry from an SN1 reaction with a chiral starting material?
answer
racemic mixture - 1:1 ratio of enantiomers
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How much ring strain in cyclopropane?
answer
?25 kcal/mole
question

What are the torsional energies of the following butane conformations:

  1. anti
  2. eclipsed II and VI
  3. eclipsed IV
  4. gauche 

 

answer

              (1)   (2)   (4)    (3)

[image]

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[image]
answer
propyl group
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[image]
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isopropyl group
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[image]
answer
tert-butyl
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[image]
answer
sec-butyl
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[image]
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butyl group
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[image]
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phenyl group
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[image]
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benzyl group
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What bond is the strongest as far as IR spectroscopy is concerned?
answer
O—H
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For ethene, what are the:

  1. hybridization state of carbons
  2. bond angles
answer
  1. sp2  
  2.  

[image]

 

question

Definitions of:

  1. BrOnsted acid
  2. BrOnsted base

 

answer
  1. proton (H+) donor
  2. proton (H+) acceptor
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Definitions of:

  1. Lewis acid
  2. Lewis base
answer
  1. electron pair acceptor
  2. electron pair donor
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