CHEM 1315 Exam 4 practice a1

Name:______________________ Roll Number ________________

1. (40 points, 4 points each) Circle the correct answer. There is only one correct answer. a. Which of the following is the best name for the following compound?

A) B) C) D) E)

Propyl isopropanoate Propanoyl isopropoxide Isopropyl propanoate Ethyl isopropyl ketone 1-Methylethyl propionate

b. In which of the following are the compounds listed in order of decreasing acidity? A) B) C) D) E) CH3CO2H > CH3CH2OH > C6H5OH > H2O C6H5OH > CH3CO2H > CH3COCH3 > CH3CH2OH CH3CO2H > H2O > C6H5OH > CH3CH2OH H2O > CH3CO2H > C6H5OH > CH3CH2OH CH3CO2H > C6H5OH > CH3CH2OH > CH3COCH3

c. What is the leaving group in the acid-catalyzed hydrolysis of acetamide (CH3CONH2)? A) B) C) D) E) NH3 H2O H3O+ + NH4 NH2

d. What product is formed from the reaction of an aldehyde with a Grignard reagent followed by addition of H+/H2O? A) B) C) D) E) a tertiary alcohol a ketone a primary alcohol a carboxylic acid a secondary alcohol

_________/ 16 Page 1 of 7

CHEM 1315 Exam 4 practice a1

Name:______________________ Roll Number ________________

e. Which of the following is a hydrate? A) B) C) D) E) CH3-CH(OH)(OCH3) CH3-CH(OCH3)-CH2CH3 CH3-C(OH)(OCH3)-CH2CH3 CH3-C(OCH3)2-CH2CH3 CH3-CH(OH)2

f. What compound can be converted to 3-methyl-3-pentanol by reaction with methyl magnesium bromide followed by hydrolysis? A) B) C) D) E) pentanal 2-pentanone 3-pentanone butanone butanal

g. Which of the following compounds is the most reactive to nucleophilic attack? A) B) C) D) E) 2,2,4,4-tetramethyl-3-pentanone 3-methyl-2-pentanone 2-pentanone 2,4-dimethyl-3-pentanone 3-methyl-2-butanone

h. What product is formed when malonic acid is heated?

A) B) C) D) E)

formaldehyde (HCHO) formic acid (HCO2H) acetic acid (CH3CO2H) propanoic acid acetaldehyde (CH3CHO)

i. What product is formed when acetone (CH3COCH3) undergoes an aldol condensation in a heated, basic aqueous solution of acetone? A) B) C) D) E) 4-methyl-4-penten-2-one 4-methyl-3-penten-2-one 3-methyl-3-penten-2-one 2,4-pentanedione 2-methyl-2,4-pentanediol

_________/ 20 Page 2 of 7

CHEM 1315 Exam 4 practice a1

Name:______________________ Roll Number ________________

j. Hydroxide is a poor leaving group in SN and E reactions. However, it is the leaving group in base catalyzed aldol condensations. Which of the following explains this observation? A) B) C) D) E) Hydroxide departs to give a very stable cation. The loss of hydroxide in the aldol condensation is not an SN or E reaction. The product of the aldol condensation is a stable resonance stabilized conjugated enone. The hydroxyl group is protonated prior to leaving in the aldol condensation. Enolates are stable in acid solutions.

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. Draw the organic product for the following reaction.

b. Draw the organic product for the following reaction.

c. What is the organic product in the following two step reaction?

_________/ 16 Page 3 of 7

CHEM 1315 Exam 4 practice a1

Name:______________________ Roll Number ________________

d. What reagents would you use in the following reaction?

e. What would be the major organic product in the following reaction?

f. Provide the systematic name for the following compound.

g. Draw the reagent for the following reaction.

h. Draw the organic product of the following reaction.

_________/ 20 Page 4 of 7

CHEM 1315 Exam 4 practice a1

Name:______________________ Roll Number ________________

i. Draw the organic product for the following reaction.

j. Provide the systematic name for the following.

_________/ 08 Page 5 of 7

CHEM 1315 Exam 4 practice a1

Name:______________________ Roll Number ________________

3. (10 Points) Multistep synthesis: Select one of the following three transformations. Part A: Provide a sequence of reactions to perform the transformation, showing the reagents and intermediate products indicated

or Part B or C: Provide a sequence of reactions to perform the transformation, showing the reagents and structures of all intermediates products. The synthesis must use the given starting material. You may use any other substrate materials and/or reagents. Do not show the mechanism.

or

_________/ 10 Page 6 of 7

CHEM 1315 Exam 4 practice a1

Name:______________________ Roll Number ________________

4.

(10 points) ) Mechanistic Understanding: We know that Benzaldehyde undergoes an acid catalyzed reaction with methyl amine to form an imine. The reverse reaction can also happen. Provide a stepwise mechanism for the acid catalyzed hydrolysis of the N-methyl imine of Benzaldehyde to Benzaldehyde. Only the empty box portion of the mechanism is required. The other steps in the mechanism are provided.

_________/ 10 Page 7 of 7