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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW*

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Select the correct name for the following compound a. 1,1-dimethylcyclopentene b. 5,5-dimethylcyclopentene c. 3,3-dimethylcyclopentene d. 2,2-dimethylcyclopentene

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* SUMMARY: Alkene Stability

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Rank the following alkenes according to their increasing stability. (least stable most stable) A. 1, 4, 3, 2 B. 1, 4, 2, 3 C. 2, 3, 1, 4 D. 2, 4, 3, 1 E. 4, 1, 2, 3 F. 3, 2, 4, 1

PRACTICE: Classify the mechanism as a substitution, elimination, or addition reaction.

a. substitution b. elimination c. addition

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* SUMMARY: Acid-Catalyzed Hydration

PRACTICE: The acid catalyzed addition of water to alkenes is a common method to prepare alcohols. For the example below, show the mechanism of this reaction. Include all flows of electrons, charges and intermediates. The mechanism MUST show how the acid is catalytic.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Draw the mechanism of the following reaction. If no reaction would occur, say so. Show stereochemistry where relevant. Show the intermediate between steps 1 and 2.

PRACTICE: Predict the product:

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* SUMMARY: Hydroboration

PRACTICE: Determine the mechanism and predict the product of the reaction:

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: How many atoms and electrons are directly involved in the bond-making and bondbreaking of the reaction given below? Choose the right answer. Addition of BH3 to an alkene a) five atoms, six electrons b) four atoms, six electrons c) three atoms, six electrons d) five atoms, four electrons e) four atoms, four electrons f) three atoms, four electrons

PRACTICE: Circle the major product of the following reaction.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Draw the alcohol that is oxidized to give the product shown below. Show all hydrogen atoms.

SUMMARY: Halogenation

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Which of the statements is most correct regarding the products expected from the halogenation reaction shown below? a) Equal amounts of I and IV are produced. b) Equal amounts of I and III are produced. c) Equal amounts of III and IV are produced. d) Equal amounts of I and II are produced. e) Equal amounts of II and III are produced.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Please provide the mechanism for the following reaction and predict the product.

SUMMARY: Halohydrin

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Give the product, or products, including stereochemistry of the reaction of (Z)-3methyl-2-pentene with the reagent below. If the products are a pair of enantiomers, you need to draw only one and state that the other enantiomer is formed. I2 / H2O

SUMMARY: Dihydroxylation

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: What is the major product of the reaction drawn below? For clarity, the other enantiomer was not drawn for those labeled as racemic.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Demonstrate knowledge of ozonolysis by providing the full arrow pushing mechanism, unambiguous structural formulas for the ozonide intermediates, and the 3 products that result from this reaction.

SUMMARY: Ozonolysis Retrosynthesis

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Supply Reagents:

SUMMARY: Oxidative Cleavage

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Provide the major product for the alkene reaction below.

SUMMARY: Alkyne Oxidative Cleavage

PRACTICE: Which of the following gives only one organic product on ozonolysis? a) 2-hexyne b) 3-hexyne c) 2-heptyne d) 3-heptyne

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Consider the structures below and answer the following questions. a. Which compound will form different products by oxymercuration and hydroboration?

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Which of the following reactions will yield a meso compound? a. 2-butyne + Cl2/CCl4 x 2 → b. 2-butene + H2O / H2SO4 → c. 2-methylcyclobutene + Hg(OAc)2, THF/ NaBH4, NaOH → d. cis-3-hexene + cold, dilute KMnO4 → e. More than one of these

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Provide an efficient multistep synthesis for the following conversion of the given starting material into product. Give all necessary reagents and catalysts, and give a structural formula of the organic product. Show stereochemistry appropriately when necessary. If a mixture of products must be present after a step, assume that you can separate the mixture and take the one needed product forward through the next step.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: What products are produced from the reaction below?

PRACTICE: Draw the apparatus for acetylene formation.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: The hydrogen on a terminal alkyne carbon is acidic (pka = 25) and with a strong enough base it can be removed.

SUMMARY: Hydrogenation of Alkynes

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: For the reaction shown, select the expected major organic product.

SUMMARY: Alkyne Hydrohalogenation

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Determine the major product for the alkyne reaction below.

SUMMARY: Alkyne Halogenation

PRACTICE: Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of Br2.

A)

1,1-dibromo-1-pentene

B)

(E)-1,2-dibromo-1-pentene

C)

(Z)-1-bromo-1-pentene

D)

A and B

E)

B and C

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* SUMMARY: Alkyne Hydration

PRACTICE: Reaction of an asymmetrical terminal alkyne with mercury sulfate and sulfuric acid in water would produce which of the following? 1. 2. 3. 4.

alkene diol aldehyde ketone

SUMMARY: Alkyne Hydroboration

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Complete the following reaction by drawing the structure of the one major organic product in the box provided.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Compound A has molecular formula C5H10. When A is treated with BH3, followed by H2O2, NaOH, H2O, a mixture of B and B’ is isolated. B and B’ each have molecular formula C5H12O. Separately, B and B’ are optically active. A 50:50 mixture of B and B’ is optically inactive, however. When the mixture of B and B’ is exposed to the Jones reagent (CrO3, H2SO4, H2O), a single compound C (C5H10O) is produced. Finally, when A is treated with O3 followed by H2O2, acetone (shown below) and Compound D (C2H4O2) are produced. Complete the reaction scheme below by drawing structures for the unknown compounds A, B, B’, C and D. Be sure to show the stereochemistry of B and B’ clearly and unambiguously!

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* SUMMARY: Alkynide Synthesis

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Predict the product of the reaction:

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Propose a mechanism for the following reaction. Include all reagents and intermediates.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Provide line-angle structures and/or names for the following (the groups Cl and Br are named chloro and bromo, respectively):

PRACTICE: Which compound has the lower boiling point: (a) CHCl 3 or (b) CH 2Cl 2? (Choose one)

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: DRAW the structures of the transition states (geometry unnecessary) for the two propagation steps (in either order) in the chlorination of chloromethane to dichloromethane, with dotted lines to represent partial bonds. You may omit δ·.

SUMMARY: Radical Stability

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Which is the most stable radical?

SUMMARY: Free Radical Halogenation

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Which of the following is the rate-determining step in the free-radical bromination of methane?

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Approximate the heat of reaction for the given halogenation reaction.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Which reaction has a favorable ΔS (entropy)?

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: How many monochloro substitution products are produced when the alkane below is chlorinated? Consider both constitutional isomers and stereoisomers. Please explain how to work these! The number of monochloro substitution products is .

PRACTICE: Transition states have partially formed bonds whereas intermediates have fully formed bonds ( True or False )

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Draw all of the monobromination products of the molecule below. Calculate the percentage yields of each product. The relative rates for each position are given below.

PRACTICE: Complete the following reaction with the correct structures of the products. Don’t forget to specify the stereochemistry.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Fill in the reagents required to effect the following transformations.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: For each of the following, supply a structural formula for the major organic product(s) when the product(s) is(are) not given: if no reaction occurs, write N.R. Provide the following when a product is given. If an organic reactant is missing, supply a structural formula; if an organic reactant (reagent) or catalyst is missing, simply give a formula. Give the best possible answers. Be sure to show stereoisomers properly when necessary.

PRACTICE: The following reaction will not occur. Explain why the reaction will fail.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* SUMMARY: SN1 Reaction

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Complete the following mechanism for an SN1 reaction that occurs when 2-chloro-2methylbutane is heated in water. NOTE, ALTHOUGH AN E1 PROCESS WILL ACCOMPANY THIS SN1 REACTION, WE ARE ONLY INTERESTED IN THE SN1 MECHANISM FOR THIS PROBLEM. Use appropriate arrows to show all movement of electrons, show all non-bonding electrons as dots and show any formal charges. If any of the species are really racemic mixtures of enantiomers, you only need to draw one stereoisomer and write "racemic". In the boxes provided, write which kind of mechanisitc element is being shown for that step, i.e. "make a bond", etc.

PRACTICE: For the following pairs of reactions, mark an “X” in the box on the right indicating which will go faster. The compound on top of the arrow is the solvent.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Select the best conditions for the reactions.

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Consider the compounds below and answer the following questions. a) Which of the compounds below will most readily react via SN1?

b) Which of the compounds below will not significantly undergo SN2 reaction?

c) True/False: Reacting compound I with CH 3CH2ONa will favor SN2 reaction.

d) Which of the compounds below will react with KCN to form a product with R-configuration?

e) Which of the compounds below will react via SN2 most readily?

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UNCG - ORGANIC CHEMISTRY I - PROF. HINDO UNCG CHE 351 HINDO EXAM 3 REVIEW* PRACTICE: Use A-G to label the graph with the structures given for the reaction:

PR...