ucf - organic chemistry 1 - prof. daoudi ... - organic chemistry 1 - prof. daoudi practice test: ucf...

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UCF - ORGANIC CHEMISTRY 1 - PROF. DAOUDIUCF PROF. DAOUDI EXAM 3 REVIEW

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UCF - ORGANIC CHEMISTRY 1 - PROF. DAOUDIPRACTICE TEST: UCF PROF. DAOUDI EXAM 3 REVIEW

PRACTICE: Identify the most stable and the least stable alkene

PRACTICE: Create the full arrow pushing mechanism which shows all intermediates and allproducts that result from these reactions. If alkenes are produced, indicate which is major andminor.

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PRACTICE: Draw the product(s) from the following reaction.

a) Clearly label each drawing with the correct stereochemistry-(use R & S for chiral centers, if any).

b) Clearly label pairs of enantiomers & diastereomers, if any.

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PRACTICE: Fill in the missing reagents

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PRACTICE: Which of the following is ( Z )-3,5-dimethyl-3-nonene?

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PRACTICE: Name the following compound correctly using accurate R or S and E and Znomenclature.

PRACTICE: Draw the product(s) from the following reaction. Show any relevant regio- and orstereochemistry and asterisk any chiral centers.

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PRACTICE: Which carbocation would not be likely to undergo rearrangement?

PRACTICE: Provide the reagents necessary to achieve the following transformation.

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PRACTICE: Rank in order of leaving group ability (1 = best leaving group, 4 = worst leaving group).

PRACTICE: Which is the order from fastest to slowest for the rates of the SN2 reactions of thesealkyl bromides with CH3S— / DMSO?

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PRACTICE: Which compound would react fastest by an S N2 mechanism?

PRACTICE: Identify the correct potential energy diagram for a tertiary alkyl chloride (3°RCl) versusprimary alkyl chloride (1°RX) undergoing an SN2 reaction. Provide rationale to support yourchoices.

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PRACTICE: In the SN2 reaction, the "2" stands for

a) two reactants in the reaction

b) two steps in the reaction

c) two intermediates in the reaction

d) bimolecular kinetics for the reaction

PRACTICE: Provide a complete mechanism for the following transformation.

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PRACTICE: Use A-G to label the graph with the structures given for the reaction:

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PRACTICE: Predict the products of the following synthesis:

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PRACTICE: Create the full arrow pushing mechanism which shows all intermediates and allproducts that result from these reactions. If alkenes are produced, indicate which is major andminor.

PRACTICE: Which solvent would favor and SN2 style mechanism?

A) Methanol

B) Dimethyl formamide

C) Water

D) Acetic acid

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PRACTICE: Rank the species below in order of increasing nucleophilicity in hydroxylicsolvents (weakest nucleophile first):

CH3CO2-, CH3S-, HO-, H2O.

a) H2O < CH3S- < CH3CO2- < HO-

b) H2O < HO- < CH3CO2- < CH3S-

c) H2O < CH3CO2- < HO- < CH3S-

d) CH3CO2 - < H2O < HO- < CH3S-

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PRACTICE: Circle “non-polar”, “polar aprotic”, or “polar protic” to describe each of the followingsolvents:

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PRACTICE: Create the full arrow pushing mechanism which shows all intermediates and allproducts that result from these reactions and label minor and major products if they are not equal inpotential energy.

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PRACTICE: Which of the following undergoes SN1 solvolysis in ethanol/water at the fastest rate?

a) A

b) B

c) C

d) D

PRACTICE: What is the nucleophile in the following reaction?

2 H2O + H3C-X H3C-OH + H3O+ + X-

a. H2Ob. H3C

c. X-

d. H3C-OH

e. H3O+

f. CH3-X

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PRACTICE: Propose a successful synthesis of 1-decene from 1-bromodecane. Be sure to includespecific reagents and solvents.

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PRACTICE: Predict the major elimination product for the following reaction:

PRACTICE: In the dehydration of 2-bromo-2-methylbutane with potassium hydroxide, whichhydrogen atom is preferentially abstracted?

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PRACTICE:

A. Predict the product of the following reaction.

B. Construct a reaction mechanism that accounts for the product proposed.

C. Construct a reaction coordinate diagram for the reaction. Label all axes. Note that the reactionhas three steps: The 1st is fast and endothermic. The 2nd is slow and endothermic. The 3rd is fastand exothermic. The overall reaction is exothermic.

D. Using complete sentences state how you have shown that the 1st and 3rd steps are fast and thatthe 2nd reaction is slow.

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PRACTICE: Propose a mechanism for the following reaction

PRACTICE: Predict the major product

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PRACTICE: Which of the following is the double substitution product of the reaction below?

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PRACTICE: The reaction shown below would be expected to produce as major products which ofthe following compounds?

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

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PRACTICE: Determine the anticipated product(s) for the reaction below. Using correctmechanistic arrows, provide the step-by-step mechanism that shows how the following substitutionreaction proceeds. You do not need to show stereochemistry while providing the mechanism, butshow correct stereochemistry in the final product(s). (Circle the major product if multiple productsare formed.)

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PRACTICE: Predict the product:

PRACTICE: Give all possible product/products and designate stereoselectivity &/or regioselectivityby using wedges and dashes.

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PRACTICE: Provide the structural formula for the reactant in the following reaction.

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PRACTICE: The reaction of Br2 to cyclohexene would produce the compound(s) represented bystructure(s): Circle all that apply

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PRACTICE: Predict the products of the following synthesis:

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PRACTICE: Give all possible product/products and designate stereoselectivity &/or regioselectivityby using wedges and dashes.


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PRACTICE: Supply a structural formula for the major organic product ; if no reaction occurs,write N.R. Give the best possible answer. Be sure to show stereoisomers properly when necessary.

PRACTICE: Draw the structural formula of the major organic product(s) in the box for the followingreaction.

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PRACTICE: Which one of these structures best explains the reason why epoxide 1 givescompound 2 instead of compound 3 upon reaction with HBr.

PRACTICE: Predict the product of the following reaction showing stereochemistry if applicable.

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PRACTICE: Predict the major product

PRACTICE: Predict the product of the following reaction. Show stereochemistry when applicable.

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PRACTICE: Complete the following set of reactions by supplying the missing reagents

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PRACTICE: For each of the following, supply a structural formula for the major organicproduct(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 structuralformula; if an organic reactant (reagent) or catalyst is missing, simply give a formula. Give the bestpossible answers. Be sure to show stereoisomers properly when necessary.

PRACTICE: Fill in the missing reagents

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PRACTICE: Predict the product for the reaction below.

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PRACTICE: What is the expected major product of the following reaction sequence?

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PRACTICE: Fill in the missing reagents:

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PRACTICE: Predict the product of the reaction:

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PRACTICE: Starting with 1-hexene, which synthetic sequence below gives 2-cyanohexane?

a) (1) H2SO4 (cat.), H2O (2) NaCN

b) (1) HBr/peroxide (2) NaCN

c) (1) HBr (2) NaCN

d) (1) Br2, H2O (2) NaCN

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PRACTICE: Provide an efficient multistep synthesis for the following conversion of the givenstarting compound into the target compound. For this problem, do not give a mechanism withcurved arrows. For the synthesis, more than one functional group transformation is required. Foreach functional group transformation, give all necessary reagents and catalysts and give astructural formula of the organic product. Also give hv and/or heat when necessary.Show stereochemistry appropriately when necessary.

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PRACTICE: Which of the given reaction schemes would produce the molecule shown below?

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PRACTICE: Predict the reagent(s) required to complete the following transformation:

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PRACTICE: Fill in the missing reagents:

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PRACTICE: Predict the major product of the reaction shown.

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PRACTICE: Compound A reacts with HBr via an SN1 process leading to 3 different constitutionalisomers. Draw the structure of these products.

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ucf - organic chemistry 1 - prof. daoudi ... - organic chemistry 1 - prof. daoudi practice test: ucf...

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