Download This exam will consist of 30-35 multiple choice or short answer

Dr. Caroline Sheppard
Chemistry 2412L
Study Guide for Exam
This exam will consist of 30-35 multiple choice or short answer questions. You should bring a calculator. An NMR
correlation table will be provided. Study for this exam by reviewing your graded lab reports and questions (including
pre-labs), reviewing the experimental procedures and techniques, and considering the following questions:
I. NMR Spectroscopy
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What is the Index of Hydrogen Deficiency? How is it calculated?
Given a molecule, how can you predict the number of signals in the 13C-NMR spectrum?
Given a molecule, how can you predict the number of signals, multiplicity, and chemical shifts in the 1HNMR spectrum?
What is an integration line? What does it tell you?
What does it mean for a proton to be shielded? Deshielded?
What is TMS? How is it used in NMR spectroscopy?
How can you determine the structure that best corresponds to a given spectrum and molecular formula?
How can IR be used to help interpret NMR spectra?
II. Nucleophilic Substitution of Alkyl Halides
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What are the major differences between SN2 and SN1 mechanisms?
Briefly explain how structure of the alkyl halide substrate affects reactivity in SN2 and SN1 reactions.
Why does 1-bromobutane react faster than 1-chlorobutane?
Explain the two types of reactions used in this experiment to determine SN2 and SN1 reactivity.
How could you tell a reaction was occurring?
What are the products under both reaction conditions (what group replaces the Br or Cl leaving group)?
Why are compounds like benzyl chloride and crotyl chloride reactive under both SN2 and SN1 conditions?
Why is bromobenzene not reactive?
III. The Grignard Reaction
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What is a Grignard reagent? How is it synthesized?
What is the solvent in the reaction?
What are the starting materials? Product? What are the structures?
What are some physical properties of the starting materials and product?
What is petroleum ether? What is the purpose of using pet ether in this experiment?
What is the mechanism of the reaction?
Why must the reaction apparatus be dry? What happens if water is present?
How are the theoretical and percent yields calculated?
What did the IR tell you in this experiment?
What is the purpose of a melting point determination? If the melting point range is short (2 degrees or less)
what significance does this have? What is the significance of a broad mp range? What if the mp range of a
compound is short, but not very close to the expected mp temperature? If a solid is not dry, what effect does
this have on the melting point determination? What did the melting point tell you in this experiment?
What is the purpose of using a drying agent on the organic layer after a separation? How can you tell if the
extracted solution is “dry”?
IV. Properties of Alcohols
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What conclusions can be made about the solubility of alcohols? How does structure affect solubility?
What is the Lucas test? What indicates a positive test? What types of alcohols react fastest? What type of
mechanism is it? Write an equation for this reaction.
What is the chromic acid test? What indicates a positive test? What types of alcohols react fastest? Write an
equation for this reaction.
What happened during the esterification reaction? What indicated a reaction had occurred? Write equations
for the esterification reactions used in this experiment.
What are the structures of the alcohols used in this experiment?
Which tests would you use to distinguish between two alcohols?
Dr. Caroline Sheppard
Chemistry 2412L
Study Guide for Exam
V. Aldehydes and Ketones
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Describe the following tests. What does each test demonstrate? What are the products formed in each? Be
able to write a reaction for each test.
o 2,4-DNP
o Semicarbazones
o Chromic acid
o Iodoform
How was IR used in this experiment? How can it be used to distinguish between aldehydes and ketones?
What is a methyl ketone? How can it be distinguished from another ketone?
What test would you use to distinguish between ketone and aldehydes?
VI. Qualitative Organic Analysis
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VII.
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VIII.
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What functional groups are generally soluble in water? Acid? Base?
Describe the following tests. What does each test demonstrate? What are the products formed in each? Be
able to write a reaction for each test.
o Beilstein
o Silver nitrate
o Chromic acid
o Lucas
o Ferric chloride
o Bromination
o Iodoform
o Potassium permanganate
o 2,4-DNP
o Ignition
o Hinsberg
How was the melting point used in this experiment?
How was IR and GC/MS data used in this experiment?
How is the empirical formula determined from elemental analysis data?
Esterification
What is a Fischer Esterification reaction? What is the mechanism?
What is the purpose of the acid in this reaction?
How could the equilibrium be shifted toward the products or the reactants?
What are some notable physical properties of esters?
How are esters named?
How is the theoretical yield calculated?
Aromatic Nitration
What is the reaction in this experiment? What are some physical properties of the reactant and product?
What is the product distribution? Why? How was this distribution determined?
What is the electrophile? Reaction mechanism? Draw the intermediate, including all resonance structures.
Is there a catalyst for this reaction? What is it? What did it do?
How is GC used in this reaction? What did the chromatogram look like? How was the chromatogram
interpreted? How could you predict which product corresponded to which peak on the chromatogram?
How was IR used in this experiment?
What are some electron-donating groups? Electron-withdrawing groups? Activators? Deactivators?
How do existing substituents affect electrophilic aromatic substitution?
General organic lab techniques:
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Melting point determination
Liquid-liquid separation using a separatory funnel
Reflux
Distillation
Gas chromatography/mass spectrometry
Infrared spectroscopy
NMR spectroscopy
Chemical literature: be familiar with how to use the CRC Handbook of Chemistry and Physics