EXAM 2

Question 1

Predict the major product or provide either the reactant (s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomer/diastereomers are formed and clearly show stereochemistry.

Answer 1

Question 2

Predict the major product or provide either the reactant (s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomer/diastereomers are formed and clearly show stereochemistry.

Answer 2

Question 3

Predict the major product or provide either the reactant (s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomer/diastereomers are formed and clearly show stereochemistry.

Answer 3

Question 4

Predict the major product or provide either the reactant (s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomer/diastereomers are formed and clearly show stereochemistry.

Answer 4

Question 5

Predict the major product or provide either the reactant (s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomer/diastereomers are formed and clearly show stereochemistry.

Answer 5

Question 6

Provide the IUPAC name for the following molecule

Answer 6

Question 7

Provide the IUPAC name for the following molecule

Answer 7

Question 8

Please assign the configuration (E vs. Z) for each of the following alkenes, where appropriate.

Answer 8

Z

Question 9

Please assign the configuration (E vs. Z) for each of the following alkenes, where appropriate.

Answer 9

Z

Question 10

Draw the Reaction Coordinate Diagram for the following reaction. Clearly label and indicate positions for starting materials, intermediates, products, transition states, Activation Energy (EA) and Heat of Reaction (ΔHo), and rate determining step (RDS).

Answer 10

Question 11

Please numerically rank the reactive intermediates in each of the following categories. [1 = most stable, 3 = most reactive (unstable).] Briefly rationalize each answer.

Answer 11

Question 12

Please provide a reasonable arrow-pushing mechanism for each of the following reactions. Note: be sure to show all resonance structures (if any), lone pairs, and formal charges!

Answer 12

Question 13

Hyperconjugation, or the overlap of a filled σ orbital with an empty unhybridized p orbital, is linked to the stability trend of carbocations. Please represent this phenomenon by explicitly drawing the hyperconjugation that occurs with an ethyl carbocation, clearly indicating the types of orbitals that are interacting, the phases of the orbitals, and hybridization of the carbons.

Answer 13

Question 14

Please provide a reasonable arrow-pushing mechanism for each of the following reactions. Note: be sure to show all resonance structures (if any), lone pairs, and formal charges!

Answer 14

Question 15

Please provide a reasonable arrow-pushing mechanism for each of the following reactions. Note: be sure to show all resonance structures (if any), lone pairs, and formal charges!

Answer 15

Question 16

Predict the major product or provide either the reactant(s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomers/diastereomers are formed and clearly show stereochemistry.

Answer 16

Question 17

Predict the major product or provide either the reactant(s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomers/diastereomers are formed and clearly show stereochemistry.

Answer 17

Question 18

Predict the major product or provide either the reactant(s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomers/diastereomers are formed and clearly show stereochemistry.

Answer 18

Question 19

Predict the major product or provide either the reactant(s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomers/diastereomers are formed and clearly show stereochemistry.

Answer 19

Question 20

Predict the major product or provide either the reactant(s) or reagents to accomplish each of the following transformations. More than 1 step may be required to complete a transformation. Note: for reactions that result in the formation of a chiral molecule, indicate that enantiomers/diastereomers are formed and clearly show stereochemistry.

Answer 20

Question 21

Please provide a reasonable synthesis for the following molecules using the starting material(s) given. You may use any additional reactants/reagents that your synthetic route may require.

Answer 21

Question 22

Please provide a reasonable synthesis for the following molecules using the starting material(s) given. You may use any additional reactants/reagents that your synthetic route may require.

Answer 22

Question 23

IUPAC Nomenclature. Provide the correct IUPAC nomenclature for the following compounds:

Answer 23

Question 24

IUPAC Nomenclature. Provide the correct IUPAC nomenclature for the following compounds:

Answer 24

Question 25

Alkene Diastereomers. Assign the alkenes in the following target molecules as either E or Z.

Answer 25

Question 26

Alkene Diastereomers. Assign the alkenes in the following target molecules as either E or Z.

Answer 26

Question 27

Numerically rank the reactive intermediates in each of the following categories. [1 = most stable, 4 = least stable] Briefly rationalize your answers.

Answer 27

Question 28

Draw the major product of the following H-X addition to alkenes:

Answer 28

Question 29

Using the curved-arrow formalism, provide a reasonable arrow-pushing mechanism for the following reaction. Note: be sure to show all lone pair electrons and formal charges!

Answer 29

Question 30

Using the curved-arrow formalism, provide a reasonable arrow-pushing mechanism for the following reaction. Note: be sure to show all lone pair electrons and formal charges!

Answer 30

Question 31

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 31

Question 32

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 32

Question 33

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 33

Question 34

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 34

Question 35

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 35

Question 36

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 36

Question 37

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 37

Question 38

Predict major product(s) for the following reactions. Make sure to draw in stereochemistry. Also, which transformations are Markovnikov or have Markovnikov mechanistic steps?

Answer 38

Question 39

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 39

SM: Alkene Product: epoxide Reagents: MCPBA/DCM Transformation: epoxidation

Question 40

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 40

SM: Alkene Product: Aldehyde Reagents: 1. O3,MeOH, -78°C/ 2. DMS or Zn, AcOH Transformation: Ozonolysis by Oxidative Cleavage

Question 41

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 41

SM: Alkene Product: cyclopropanation [CH2] carbene Reagents: Simmons Smith: CH2I2/Zn(Cu), Et2O Transformation: cyclopropanation

Question 42

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 42

SM: Alkene Product: cyclopropane [CCl2] Reagents: KOH/CHCL3 Transformation: cyclopropanation

Question 43

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 43

SM: Alkene Product: Alkane Reagents: H2/Pd/C Transformation: Reduction catalytic hydrogenation (syn reduction)

Question 44

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 44

SM: Alkene Product: Syn-glycol Reagents: a) OsO4,pyr/NaHSO3,H2O Transformation: Syn-hydroxylation

Question 45

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 45

SM: Syn-glycol Product: Aldehyde Reagents: HIO4/H2O-THF Transformation: oxidative cleavage

Question 46

Draw the mechanism for the following reaction

Answer 46

Question 47

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 47

Question 48

Identify what has changed in each transformation. Provide reagents to accomplish this transformation.

Answer 48

Question 49

Provide the correct IUPAC nomenclature for the following compound

Answer 49

Question 50

Provide the correct IUPAC nomenclature for the following compound

Answer 50

Question 51

Provide the correct IUPAC nomenclature for the following compound

Answer 51

Question 52

Draw a reasonable arrow-pushing mechanism for the following transformation

Answer 52

Question 53

Predict major product(s) for the following reactions.

Answer 53

Question 54

Predict major product(s) for the following reactions.

Answer 54

Question 55

Predict major product(s) for the following reactions.

Answer 55

Question 56

Predict major product(s) for the following reactions.

Answer 56

Question 57

Predict major product(s) for the following reactions.

Answer 57

Question 58

Predict major product(s) for the following reactions.

Answer 58

Question 59

Predict major product(s) for the following reactions.

Answer 59

Question 60

For each of the following (1) identify what’s changed, and (2) provide the conditions to accomplish the transformation:

Answer 60

Question 61

For each of the following (1) identify what’s changed, and (2) provide the conditions to accomplish the transformation:

Answer 61

Question 62

Hydroboration-oxidation converts alkenes into

Answer 62

alcohols with anti-Markovnikov regiochemistry.