CHEM 1315 Exam 4 Practice C

CHEM 1315 Exam 4 Practice c
Name:______________________ Roll Number ________________
1. (40 points, 4 points each) Circle the correct answer. There is only one correct answer. a. A) B) C) D) E) b. A) B) C) D) E) c. A) B) C) D) E) d. A) B) C) D) E) e. A) B) C) D) E) Which of the following reactions would not give the indicated product? methylbenzoate + ammonia to give benzamide + methanol phenyl acetate + methanol to give methyl acetate + phenol propanamide + methanol to give methyl propanoate + ammonia acetic anhydride + methanol to give methyl acetate + acetic acid acetyl chloride + hydroxide to give acetic acid + chloride Which of the following will result in the formation of a carboxylic acid? Hydrolysis is reaction with water. hydrolysis of an acid anhydride with heat hydrolysis of an acyl halide acid-catalyzed hydrolysis of an amide acid-catalyzed hydrolysis of a nitrile all of the above What happens to the hybridization of the carbonyl carbon upon addition of a nucleophile? It changes from sp3 to sp2. It changes from sp3 to sp. It changes from sp2 to sp3 It changes from sp to sp3. The hybridization does not change. Acetyl chloride undergoes nucleophilic substitution at a faster rate than does methyl acetate because the ester is more sterically hindered than the acyl chloride. the acyl chloride is more sterically hindered than the ester. esters hydrolyze faster than acyl chlorides. chloride ion is a better leaving group than methoxide ion. methoxide ion is a better leaving group than chloride ion. Which of the following reactions can be used to form 3-methyl-3-hexanol? 2-butanone + propylmagnesium bromide followed by addition of H+/H2O 2-pentanone + ethylmagnesium bromide followed by addition of H+/H2O 2-pentanone + methylmagnesium bromide followed by addition of H+/H2O a and b a and c
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f.
What is the systematic name of the following compound?

O
A) B) C) D) E) g. A) B) C) D) E) h.
4,6,6-trimethyl-3-hexanone 2,4-dimethyl-5-heptanone ethyl isohexyl ketone 4,6-dimethyl-3-heptanone 4-methyl-3-octanone Carbonyl compounds can be reduced to alcohols using sodium borohydride followed by addition of H+/H2O. Which statement best describes the mechanism? addition of a hydrogen radical, followed by addition of a second hydrogen radical addition of a hydride ion, followed by addition of water addition of a hydride ion, followed by addition of a proton addition of a hydride ion and a proton more or less at the same time addition of a proton, followed by addition of a hydride ion What is the main reason that a hydrogen bonded to the alpha carbon adjacent to a carbonyl carbon is more acidic than a hydrogen of an alkane?
A) The carbonyl group is an electron-donating group and weakens the C-H bond in the alpha-position. B) The negative charge is stabilized by its proximity to the negatively charged carbonyl carbon. C) The negative charge is delocalized, and most of the charge resides on the electronegative carbonyl oxygen. D) The negative charge is delocalized, and most of the charge resides on the alpha-carbon. E) The carbonyl group is an electron-withdrawing group and weakens the C-H bond in the alpha-position. i. A) B) C) D) E) Which of the following represents the correct relative acidities for the alpha hydrogens in the compounds listed? -keto esters > ketones > esters > amides -keto esters > ketones > amides > esters amides > esters > -keto esters > ketones ketones > esters > -keto esters > amides esters > -keto esters > ketones > amides
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j. A) B) C) D) E)
Which of the following compounds is the most acidic? propanenitrile ethyl acetoacetate (CH3COCH2COOCH2CH3) ethyl acetate 2,4-pentanedione Acetone
2. (40 points, 4 points each) SHORT ANSWER. Draw the structure, or write the word or phrase that best completes each statement or answers the question. a. What is the name of the following compound?
b. The pKa of HCl is -7 and the pKa of CH3OH is 15.5. What would you expect the outcome of the reaction of methyl acetate with the chloride ion to be?
c. What is the product of the following reaction?

O O
+
H3C
NH2
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d. What are the products of the following reaction? Account for all atoms in the products.
e. Which ketone is more reactive 4-methyl-3-hexanone or 5-methyl-3-hexanone? Provide a brief explanation why it is more reactive.
O O
Circle A or B Explanantion:
f. What two reagents are needed to complete the following reaction?
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g. What is the result of the reaction of sodium borohydride (NaBH4) and methyl propanoate?
h. What product is formed when methyl ethyl ketone (2-butanone) is reacted with excess methanol in the presence of an acid catalyst?
i. How many alpha or enolizable hydrogens are present in the following molecule?
j. What is the Aldol condensation product of the reaction of 2 equivalents of propanal in a base catalyzed reaction followed by heating in acid?
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3. (10 points) Which is the stronger acid, an amide or an amine? Explain your selection with either a drawing or brief description.
4. (10 points) Provide a step-by-step mechanism for the acid catalyzed formation of the hemiketal from reacting ethanol and cyclohexanone.
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Chapter 2 slide 15
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CHEM 1315 Exam 4 Practice C

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CHEM 1315 Exam 4 Practice c

Name:______________________ Roll Number ________________