CHE 230: Organic Chemistry I Instructor: Andy Mitchell

Study Guide #3 (CH 10-12,15)

These are past exam questions, but please use

this as a STUDY GUIDE ONLY. You should

also work end of chapter problems.

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1) Provide COMMON NAMES for the following:

2) Provide IUPAC NAMES for the following:

3) Draw SKELETAL STRUCTURES for each:

4) Label the following alkenes as E or Z:

5) Circle the most stable alkene:

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6) Circle ONE COMPONENT of this endothermic reaction that, according to Le Chatelier’s principle, may be removed by distillation to drive the equilibrium toward products:

7) Draw the Reaction Coordinate Energy Diagram for the addition

reaction shown below. Clearly label Energy and Reaction Coordinate axes, actual (not abbreviations) starting materials, intermediates, and products, Ea for the rate-determining step only, and ∆H˚ for the overall reaction:

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8) With only structures (total of 5 for full credit) and fishhook

arrows, explain why a phenol is effective at trapping a radical (R.) by drawing both products of the following reaction:

9) Draw the products of the following reaction (no stereochemistry

necessary); there should be five total structures:

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10) Provide suitable reagent(s) to convert the following starting materials to products:

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11) Provide best SINGLE PRODUCT corresponding to conditions and show stereochemistry if necessary:

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12) CHOOSE ONLY THREE mechanisms from the following and draw ONLY ONE PER BLANK PAGE. YOU MUST SHOW

ALL relevant intermediates, resonance structures, curved arrows, and by-products for full credit. ONLY ONE MECHANISM PER

PAGE will be graded; any additional mechanisms WILL NOT BE

GRADED:

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Mechanism 1 of 3

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Mechanism 2 of 3

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Mechanism 3 of 3

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13) Choose ONLY TWO mechanisms from the following and draw ONLY ONE PER BLANK PAGE. YOU MUST SHOW ALL relevant intermediates, resonance structures, curved arrows, and by-products for full credit. ONLY ONE MECHANISM PER

PAGE will be graded; any additional mechanisms WILL NOT

BE GRADED:

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Mechanism 1 of 2

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Mechanism 2 of 2

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14) Provide a reasonable synthesis of 2-butanone from 1-butanol using any reaction covered to date; only reagents are necessary, not

mechanisms:

15) Provide a reasonable synthesis of adipaldehyde from cyclohexane

using any reaction covered to date; only reagents are necessary,

not mechanisms:

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16) Show product(s) for both reactions; no stereochemistry:

17) Draw the resonance hybrid ONLY for the allyl radical:

18) Draw a starting material to synthesize the alkyl bromide:

19) Draw three products for the following reaction; two should be a

racemic mixture and a third should be achiral:

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20) Draw ALL product(s) for the following reaction; stereochemistry

must be shown if necessary:

21) Show the correct carbon radical intermediate in two dimensions

only below the reaction in order to explain the outcome:

22) Show the correct carbon radical intermediate in two dimensions

only below the reaction in order to explain the outcome:

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23) Draw the mechanism for the following reaction; you must show all

unpaired electrons and clearly draw all arrows properly to indicate electron movement. You must also show Initiation, Propagation 1, Propagation 2, but ONLY ONE of the three possible Termination steps:

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24) Calculate the Degrees of Unsaturation for cyclohexene: 25) Label the following alkene as E or Z:

26) Explain with ONLY TWO WORDS why an epoxide is more

reactive than tetrahydrofuran:

27) Circle ONLY ONE COMPONENT of this endothermic reaction

that, according to Le Chatelier’s principle, may be removed by distillation to drive the equilibrium toward products:

28) Circle the most stable alkene:

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29) CHOOSE ONE OF THE FOLLOWING MECHANISMS:

Draw a mechanism with VERY ACCURATE curved arrows and ALL pertinent lone pairs (i.e. formal charges must accurately

represent the atom and accompanying lone pairs) to indicate the movement of electrons in order to explain the reaction shown; you must show ALL intermediates and by-products at the appropriate

stages for full credit:

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30) CHOOSE ONE OF THE FOLLOWING MECHANISMS:

Draw a mechanism with VERY ACCURATE curved arrows and ALL pertinent lone pairs (i.e. formal charges must accurately

represent the atom and accompanying lone pairs) to indicate the movement of electrons in order to explain the reaction shown; you must show ALL intermediates and by-products at the appropriate

stages for full credit:

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31) Provide a retrosynthesis using any reaction covered so far. You may use reactions that provide mixtures of products, but keep in mind there may be “better” options that would give selectivity. Only

reagents are necessary, not mechanisms:

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32) Provide COMMON NAMES for the following:

33) Provide the IUPAC NAME for the following:

34) Draw a SKELETAL STRUCTURE for the following:

35) Calculate Degrees of Unsaturation for 1,5-heptadiyne:

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36) CHOOSE ONE OF THE FOLLOWING MECHANISMS:

Draw a mechanism with VERY ACCURATE curved arrows and ALL pertinent lone pairs (i.e. formal charges must accurately

represent the atom and accompanying lone pairs) to indicate the movement of electrons in order to explain the reaction shown; you must show ALL intermediates and by-products at the appropriate

stages for full credit:

23

37) CHOOSE ONE OF THE FOLLOWING MECHANISMS:

Draw a mechanism with VERY ACCURATE curved arrows and ALL pertinent lone pairs (i.e. formal charges must accurately

represent the atom and accompanying lone pairs) to indicate the movement of electrons in order to explain the reaction shown; you must show ALL intermediates and by-products at the appropriate

stages for full credit:

24

38) CHOOSE ONE OF THE FOLLOWING MECHANISMS:

Draw a mechanism with VERY ACCURATE curved arrows and ALL pertinent lone pairs (i.e. formal charges must accurately

represent the atom and accompanying lone pairs) to indicate the movement of electrons in order to explain the reaction shown; you must show ALL intermediates and by-products at the appropriate

stages for full credit:

25

39) CHOOSE ONE OF THE FOLLOWING MECHANISMS:

Draw a mechanism with VERY ACCURATE curved arrows and ALL pertinent lone pairs (i.e. formal charges must accurately

represent the atom and accompanying lone pairs) to indicate the movement of electrons in order to explain the reaction shown; you must show ALL intermediates and by-products at the appropriate

stages for full credit:

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40) Provide the best, single, major, and final organic product ONLY; you do not need to show inorganic by-products:

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41) Provide the best, single, major, and final organic product ONLY; you do not need to show inorganic by-products:

CrO3

H2SO4

i) LiAlH4

ii) H2O (xs)

H3C

OH CrO3

N H Cl

H3C

OH

CH3

O

CH3

H2, Pd/CaCO3

Pb(OAc)2

quinolineLindlar Catalyst

H

OH OH S

Cl

i)

ii) SM (diol)iii)

N(Et3N)

Cl

O

H3C HCH3

H

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42) For each reaction, draw both enantiomers that would be produced.

FOR THE SOLE ENANTIOSELECTIVE REACTION, DRAW BOTH POSSIBLE ENANTIOMERS AND CIRLCE

THE PREFERRED ENANTIOMER; you do not need to show inorganic by-products:

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43) Provide a retrosynthesis using any reaction covered so far. You may use reactions that provide mixtures of products, but keep in mind there may be “better” options that would give selectivity. Only

reagents are necessary, not mechanisms: