CHEM 1315 Exam 4 Practice b

Name:______________________ Roll Number ________________

1. (40 points, 4 points each) Circle the correct answer. There is only one correct answer. a. What is the IUPAC name of the following compound?
O

Ph

N(CH3)2

A) B) C) D) b. A) B) C) D) E) c. A) B) C) D) E) d. A) B) C) D) E) e. A) B) C) D) E)

dimethylamino-3-phenylpropanoic acid N,N-dimethyl 2-phenylethyl amide N,N-dimethyl 3-phenylpropanamide dimethyl 2-phenylpropanoylamine Which of the following pairs of compounds could be used to prepare propyl butanoate? butanoyl chloride and 1-propanol propanoyl chloride and 1-butanol butanamide and 1-propanol butanoyl chloride and phenol butanoyl chloride and 1-pentanol Which of the following gives the correct relative reactivities? ester > acyl halide > amide carboxylic acid > acid anhydride > ester acid anhydride > amide > ester ester > amide > carboxylic acid acyl chloride > ester > amide What product is formed from the following reaction sequence: butyl bromide + sodium cyanide, followed by addition of HCl, water, and heat? pentanamide pentanoic acid protonated 1-pentanamine protonated 1-butanamine butanoic acid What Grignard reagent is needed to convert 2-pentanone to 3-methyl-3-hexanol? pentylmagnesium bromide ethylmagnesium bromide butylmagnesium bromide propylmagnesium bromide methylmagnesium bromide Page 1 of 6

CHEM 1315 Exam 4 Practice b

Name:______________________ Roll Number ________________

f. A) B) C) D) g. A) B) C) D) E) h.

Which of the following is not a true statement? An ester reacts with a Grignard reagent to form a tertiary alcohol. A ketone reacts with a Grignard reagent to form a tertiary alcohol. An ester reacts with a hydride ion to form a secondary alcohol. An aldehyde reacts with a Grignard reagent to form a secondary alcohol. Which of the following compounds is a hemiacetal? CH3CH2CH(CH3)2 CH3CH2CH(OCH3)CH3 CH3CH2OCH(CH3)OCH3 CH3CH2CH(OH)CH3 CH3CH2CH(OH)OCH3 What is the major organic product obtained from the following reaction?
1 O NaOH, H2O H 3 O O 2 H O O

A) B) C) D)

1 2 3 4

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CHEM 1315 Exam 4 Practice b

Name:______________________ Roll Number ________________

i.

What is the major organic product obtained from the following reaction?
O O
+ NaOH, H2O

Ph

O
1 2

O
3

O
4

O Ph Ph

Ph

Ph

A) B) C) D) j. A) B) C) D) E)

1 2 3 4 Which of the following carbonyl compounds would give the largest amount of enol when dissolved in water? hexanal 3-hexanone 3,4-hexanedione 2,4-hexanedione 2,5-hexanedione

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. Name the following compound

b. Draw the structure for the following compound.

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CHEM 1315 Exam 4 Practice b

Name:______________________ Roll Number ________________

c. What products would be formed from the acid-catalyzed hydrolysis of the following ester?
O

d. Give the products of the following reaction.

e. What organic product would be formed when the following compound reacts with CH3MgBr followed by the addition of acid?

f. What product is obtained from the reduction of the following compound with sodium borohydride, NaBH4, followed by the addition of acid?

methyl phenyl ketone

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CHEM 1315 Exam 4 Practice b

Name:______________________ Roll Number ________________

g. What product is formed from the acid-catalyzed reaction of methanol and the aldehyde below?

h. Draw the most stable enol tautomer for the following compound

i. Give the Claisen condensation product of the following reaction.

j. Draw the major product for the following decarboxylation reaction.

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CHEM 1315 Exam 4 Practice b

Name:______________________ Roll Number ________________

3. (10 points) Fill in the boxes for the following synthesis.

4. (10 points) Fill in the boxes for the following synthesis.

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