Test 3 Review

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mckenzielarmstrong
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Test 3 Review
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2013-04-07 22:22:09
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Test 3 Review
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  1. Which of the following is not true regarding carboxylic acids?
    A. Carboxylic acids are almost completed dissociated in water
    B. Carboxylic acids with five or fewer carbon atoms quite water-soluble.
    C. The carbon atom of formic acid, HCOOH, is sp2 hybridized.
    d .The carbon-oxygen bonds of the formate anion (HCOO-) are the same length.
    A. Carboxylic acids are almost completed dissociated in water
    (this multiple choice question has been scrambled)
  2. Which of the following statements is not true?
    A. Carboxylic acids are much weaker acids than HCl.
    B. Resonance stabilization of the carboxylate anion helps to explain the greater acidity of carboxylic acids than alcohols.
    C. Alkali metal salts of low molecular weight carboxylic acids are generally quite soluble in water.
    D. The value of the acidity constant, Ka, for an acid dissolved in water is given by: Ka = [RCOO-][H3O+]/[RCOOH][H2O].
    D. The value of the acidity constant, Ka, for an acid dissolved in water is given by: Ka = [RCOO-][H3O+]/[RCOOH][H2O].
    (this multiple choice question has been scrambled)
  3. alkylbenzenes + 
    KMnO4, H2O, heat, followed by H3O -->
    COOH (due to oxidation of the side chain)
  4. C(=O)H --> C(=O)OH
    Reagent?
    AgO,NH4,OH

  5. A. BH3, THF; followed by H3O+
    B. LiAlH4, THF; followed by H3O+
    C. CrO3, H3O+
    D. Ag2O, NH4OH
    A. BH3, THF; followed by H3O+ :Treatment of a carboxylic acid with borane results in reduction to give a 1° alcohol. Borane does not react with nitro groups (wheras LiAlH does!)
    (this multiple choice question has been scrambled)
  6. Carboxylic acids are reduced to 1* alcohols via 
    ______ OR ____
    • LiAlH4
    • or
    • BH3
  7. Nitriles (CN) can be reduces to 1* amines by reaction with
    LiAlH3
  8. Nitriles (CN) can be converted into ____ by warming in the presence of a strong acid, such as H3O+
    COOH
  9. The addition of a Grignard reagent (MgBr attached to anything) to a nitrile  (CN) yields a _____
    Ketone
  10. 2: Treatment of a carboxylic acid with ethanol in the presence of a small amount of a strong acid results in a Fischer esterification reaction to form an ethyl ester.
  11. COOH + EtOH with acid -->
    ethyl ester
  12. 2: CH3COCl undergoes nucleophilic acyl substitution reaction with sodium benzoate by an addition-elimination reaction to give a mixed anhydride.

  13. A. LiAlH4, ether; followed by H3O+
    B. Ag2O, NH4OH
    C. H2O
    D. LiAlH[OC(CH3)3]3, ether; followed by H3O+
    D. LiAlH[OC(CH3)3]3, ether; followed by H3O+ : Li reduces to aldehyde, which isn't subject to further Li reduction
    (this multiple choice question has been scrambled)
  14. 1: COOH + MeOH results in esterification to give the corresponding methyl ester. Further rxn with Grignard reagent (MgCl) results in a 3° alcohol. The product has two identical substituents on the oxygen-substituted carbon atom which are introduced from the Grignard reagent.
  15. 2: amide + LiAlH4 results in a reduction reaction to give an amine. The =O is reduced, BUT THE C-N OS IS NOT BROKEN and the product is NOT a 1*OH
  16. 2:   Rxn of CN with LiAlH4 & H2O --> reduction reaction to give a 1° amine.
  17. 3: CN + Grignard reagent (MgCl)-->imine + H2O-->ketone
  18. 1
  19. Which of the following steps occurs first in the mechanism of Fischer esterification?
    A. attack of the nucleophile on the carbonyl carbon
    B. formation of an oxonium ion
    C. loss of water from the tetrahedral carbonyl addition intermediate
    D. formation of the tetrahedral carbonyl addition intermediate
    E. proton transfer to solvent
    B. formation of an oxonium ion
    (this multiple choice question has been scrambled)
  20. IUPAC name?
    trans-2-hexenedioic acid
  21. Predict the outcome of this acid-base rxn


  22. A. 1. LiAlH4, ether ; 2. H2O
    B. NaBH4, EtOH
    C. H2 / Pt
    d. all of the above
    e. none of the above
    A. 1. LiAlH4, ether ; 2. H2O
    (this multiple choice question has been scrambled)
  23. What is the tetrahedral carbonyl addition intermediate (TCAI) for the Fischer esterification of ethanol and benzoic acid?
  24. What is the enol intermediate in the decarboxylation of ethylpropanedioic acid?

  25. Reaction type?
    Nucleophilic acyl substitution
  26. Which of the following is false with respect to phosphoric anhydrides and acid anhydrides?
    A. Phosphoric anhydrides have two double bonds that share a common phosphorus atom, while acid anhydrides have two double bonds that share a common oxygen atom.
    B. Both types of anhydrides possess a double bond.
    C. The phosphorous atom of a phosphoric anhydride has a different hybridization than the carbonyl carbon of an acid anhydride.
    D. Acid anhydrides are bonded to fewer oxygen atoms.
    E. Phosphoric anhydrides do not possess an acyl group.
    A. Phosphoric anhydrides have two double bonds that share a common phosphorus atom, while acid anhydrides have two double bonds that share a common oxygen atom.
    (this multiple choice question has been scrambled)

  27. A. 1. K2Cr2O7 / H2SO4 ; 2. NH3 ; 3. NaBH4 / EtOH
    B. 1. PCC / CH2Cl2 ; 2. LiAlH4 / Et2O ; 3. H2O / HCl ; 4. NH3
    C. 1. NH3
    D. 1. K2Cr2O7 / H2SO4 ; 2. SOCl2 ; 3. NH3 ; 4. LiAlH4 / Et2O ; 5. H2O / HCl
    E. 1. PCC / CH2Cl2 ; 2. NH3 ; 3. NaBH4 / EtOH
    D. 1. K2Cr2O7 / H2SO4 ; 2. SOCl2 ; 3. NH3 ; 4. LiAlH4 / Et2O ; 5. H2O / HCl
    (this multiple choice question has been scrambled)

  28. A. 1. 2 PhMgBr ; 2. H2O / HCl
    B. 1. H+ / CH3OH ; 2. 2 PhMgBr ; 3. H2O / HCl
    C. 1. SOCl2 ; 2. 2 PhOH
    D. 1. H+ / CH3OH ; 2. 2 PhOH
    E. 1. H+ / PhOH
    B. 1. H+ / CH3OH ; 2. 2 PhMgBr ; 3. H2O / HCl
    (this multiple choice question has been scrambled)
  29. 3: In the absence of a Lewis acid catalyst such as FeBr3, treatment of acetophenone with Br2 in acetic acid does not result bromination of the ring.
  30. 4: Heating this 3-ketocarboxylic acid results in decarboxylation to give a ketone and CO2. This does not result in benzoic acid.
  31. 4:  This is an acetoacetate ester synthesis in which the enolate derived from ethyl acetoacetate is alkylated and the product of this reaction is subjected to hydrolysis followed by decarboxylation. This will give a methyl ketone. This structure, a carboxylic acid, could be prepared by a malonate ester synthesis.
  32. 1: This reaction sequence consists of a malonate ester synthesis in which diethyl malonate is sequentially alkylated with iodomethane followed by 1-bromoethane, and then hydrolyzed and decarboxylated. The resulting carboxylic acid is then treated with methanol in the presence of acid to form a methyl ester
  33. 3: This rxn consists of an acetoacetate ester synthesis in which ethyl acetoacetate is sequentially alkylated with 3-bromo-1-propene followed by iodomethane, and then hydrolyzed and decarboxylated. The resulting methyl ketone is then treated with lithium aluminum hydride (LiAlH4).
  34. 1:  Treatment of a ketone with lithium diisopropylamide (LiN(i-Pr)2, LDA), a strong base, results in deprotonation to give an enolate which is subject to alkylation with methyl iodide.
  35. 4:  Rxn of an ester with LDA results in deprotonation of the α-position. The resulting enolate undergoes alkylation upon treatment with iodomethane. This does not result in a 3° alcohol. This structure could be prepared by reaction of the starting material with two equivalents of a Grignard reagent.
  36. 1
  37. 3
  38. 3
  39. 3
  40. 3

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