Which of the following best describes the key mechanistic steps ...

[erika]

Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester?
   
  a.
  elimination followed by addition
   
  b.
  addition followed by decarboxylation
   
  c.
  addition followed by elimination
   
  d.
  substitution followed by addition

Question 2

Which of the following is the correct order of decreasing acid strength of the following compounds (more acidic > less acidic)?
 
   

   
  a.
  1 > 2 > 3
   
  b.
  2 > 3 > 1
   
  c.
  1 > 3 > 2
   
  d.
  3 > 2 > 1

Question 3

Which of the following compounds is a 2 amide?
   
  a.
 
   
  b.
 
   
  c.
 
   
  d.
 

Question 4

What is the correct assignment of the functional groups in the following compounds?
 
   

   
  a.
  1 = acid chloride; 2 = ester; 3 = nitrile
   
  b.
  1 = carboxylic acid; 2 = ester; 3 = imide
   
  c.
  1 = acid chloride; 2 = ester; 3 = amide
   
  d.
  1 = acid anhydride; 2 = ester; 3 = imide

Question 5

Which of the following is the correct assignment of the classes of the following compounds?
 
   

   
  a.
  1 = lactone; 2 = ester; 3 = amide
   
  b.
  1 = ester; 2 = ester; 3 = imide
   
  c.
  1 = ester; 2 = imide; 3 = amide
   
  d.
  1 = lactone; 2 = anhydride; 3 = imide

Question 6

What is the correct assignment of the names of the following substituted benzenes?
 
   

   
  a.
  1 = benzoyl chloride; 2 = benzyl amine; 3 = benzyl alcohol
   
  b.
  1 = benzyl amine; 2 = benzoyl chloride; 3 = benzamide
   
  c.
  1 = benzamide; 2 = benzoyl chloride; 3 = benzoic acid
   
  d.
  1 = benzoyl chloride; 2 = benzamide; 3 = benzoic acid

Question 7

What is the IUPAC name of the following compound?
 
   

   
  a.
  dimethylamino 3-phenylpropanoic acid
   
  b.
  N,N-dimethyl 2-phenylethyl amide
   
  c.
  N,N-dimethyl 3-phenylpropanamide
   
  d.
  dimethyl 2-phenylpropanoylamine

Question 8

Instructions: Tell which spectroscopic technique you would use to distinguish between the two members of the pair. Tell what differences you would expect to see.
 

Identify spectroscopic technique:
 
   

Question 9

Instructions: Tell which spectroscopic technique you would use to distinguish between the two members of the pair. Tell what differences you would expect to see.
 

Identify spectroscopic technique:
 
   

[stanleka1]

Answer to Question 1

c

Answer to Question 2

b

Answer to Question 3

c

Answer to Question 4

c

Answer to Question 5

d

Answer to Question 6

d

Answer to Question 7

c

Answer to Question 8

IR

1820, 1760 cm¹

(anhydride)
25003300 cm¹ (acidOH)
17101760 cm¹ (carboxyl)
1715 cm¹(ketone)

¹H NMR
one triplet
one quartet
three overlapping triplets
one quartet
one singlet

Answer to Question 9

IR

1735 cm¹

(aliphatic ester)

1720 cm¹

(aromatic ester)

¹H NMR
methyl singlet
methylene singlet
one triplet
one quartet

Answer to Question 10

IR
2250 cm¹
1650 cm¹
IR spectroscopy would differentiate these two compounds based solely on the nitrile absorption in the first compound and the carbonyl of the N,N disubstituted of the amide in the second.

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Answer to Question 17

[erika]

Excellent

[phuda]

TYSM