CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

1. (40 points, 4 points each) Circle the correct answer. There is only one correct answer. a. What is the major organic product obtained from the following reaction?

CH3OH HCl

H3CO OCH3
1 2

OCH3
3 4

OCH3

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

1 2 3 4 Which of the following would undergo electrophilic addition of HBr with the highest regioselectivity? 3-heptene 2-hexene 1-hexene 1-methylcyclohexene 3-methylcyclohexene What combination of alkyne and alkyl halide would be the best to use for the synthesis of 3-heptyne? 1-pentyne and 1-bromopropane 2-butyne and 1-bromopropane 1-hexyne and bromomethane 1-butyne and 1-bromopropane 1-pentyne and bromoethane What product is obtained when 2-pentyne undergoes hydrogenation in the presence of Lindlar's catalyst (Pd/CaCO3 in quinoline)? trans-2-pentene cis-2-pentene pentane cis-1-pentene mixture of (A) and (B)

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CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

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

Which position in the benzyl carbocation (C6H5CH2+) has the least amount of positive charge? the carbon attached to the benzene ring C2 (ortho) C3 (meta) C4 (para) They all have the same partial positive charge What is the hybridization of the carbon atoms in benzene (C6H6)? All are sp. Three carbon atoms are sp2, and three are sp3. All are sp2. All are sp3. Three carbon atoms are sp, and three are sp2. Which of the following is not required for a molecule to be aromatic? Every atom on the ring must have a p orbital in a continuous ring. The molecule must have 4n + 2 pi electrons. All of the atoms must be sp hybridized. The molecule must be cyclic. The molecule must be flat. Which of the following ions is anti-aromatic?

A) B) C) D) E) i. A) B) C) D) E)

1 2 3 4 1 and 3 Which of the following compounds has one chiral center? 3-chloropentane 1-chloropropane 1-chloropentane 2-chloropropane 2-chloropentane Page 2 of 8

CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

j.

Which of the following 2-bromobutane structures is an S configuration?

Br CH3 H 1 CH3 CH3CH2 2

Br

H H3C H

Br

Br

CH3 H CH2CH3 4

CH3CH2

CH2CH3 3

A) B) C) D)

1 2 3 4

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 major product for the following reaction.

b. Draw the major reactant for the following reaction

OMe

+ MeOH

H+

Me

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CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

c. Which species is more stable? Give a brief explanation why it is more stable

d. Draw the major product for the following reaction

e. Rank the following compounds in order of decreasing acid strength?

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CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

f. Draw the resonance contributors for the following species. Indicate the major and minor contributors to the resonance hybrid. You do not need to draw the resonance hybrid. Hint: methoxy is a CH3O substituent group.

g. Which ion in the following pair is more stable? Explain your choice.

h. Draw the major product for the following reaction

CH3

HNO3 H2SO4

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CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

i. Draw the major product for the following reaction

j. Name the following chiral molecule

3. (10 points) Draw all the resonance contributors for the following ion

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CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

4.

(10 points) ) For this question you may answer either part A or Part B below. Clearly indicate which part that you would like graded. Otherwise Part A will be graded.

PART A Multistep synthesis: Select one of the following two transformations. 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.
HC CH H3C

OR
CH3

NO2

Part A option

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CHEM 1315 Exam 2 Practice c

Name:______________________ Roll Number ________________

Or PART B: Mechanism: The substrate, reagent and product are given for the following Friedel Crafts alkylation reaction. Draw the mechanism for the two key organic intermediates that lead to the product shown. Use curved arrows to show the movement of electrons for the conversion of intermediate one to intermediate two.

Cl

AlCl3 Part B option AlCl3 AlCl4

C6H6

intermediate 1

intermediate 2

intermediate 3

1. 2. 3. 4.

40________ 40________ 10________ 10________

Total 100 ________

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