Practice Exam 3

1. (19 pts) (a) Circle the group with the higher Cahn Ingold Prelog priority in each of the following pairs (6 pts.).
H 3C 1) and C CH

2)

NHCH3

and

CH2

CH3

CH3

3)

CH2

and Br

CH2 OH

(b)

The sex attractant of the codline moth is the 2Z, 6E stereoisomer of the molecule below. Write the structure of this substance in a way that clearly shows its stereochemistry. (4 pts).
CH3CH2CH2C=CHCH2CH2C=CHCH2OH CH3 CH2CH3

(c)

Provide the IUPAC names for the following compounds. Be sure to designate E or Z stereochemistry for part (i) (6 pts).
OH
(i) (ii)

Cl

(d)

Draw a structure for the following molecule (3 pts):

4-methyl-4-penten-2-ol

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2. (38 pts) Draw the principal organic product expected from each of the following reactions. If more than one product is expected, be sure to indicate which is the major product. Pay particular attention to STEREOCHEMISTRY AND REGIOCHEMISTRY where appropriate. (a)
H CH3 CH3 Br K+ -OC(CH3)3 HOC(CH3)3

(b)
HOC(CH2CO2H)2 CO2H citric acid H2SO4

(c)
Br CH3 CH3CH2O-Na+ CH3CH2OH

(d)
HO CN KHSO4 H3CO heat

(e)
2-methyl-2-butene HBr peroxides

(f)
CH3 CH3 H2 Pt

Which reaction part above involves a non-Zaitsev elimination?_________ (2 pts)

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(g)
CH3 Br2 H2O

(h)
O Cl O H O

(i)
HCl

(j)
H2O H2SO4 CH3 (catalytic amount)

(k)
CH3 CH3 B2H6 H2O2 NaOH

(l)
1. O3 2. (CH3)2S

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3 . (13 pts ) Complete the following questions: (a)The carbocation below has the potential to rearrange to a more stable carbocation. Write the structure of the rearranged carbocation (3 points).

(CH3)2CH CH CH3

(b)

Draw out the alkenes you would expect to get from the E2 elimination of 2-bromo-2-methylpentane (4 pts).

(c)

The reaction of 1-butene with bromine, Br2, in aqueous solution gives primarily 1-bromo-2-butanol. Identify the nucleophilic species in the reaction (3 pts). A.Br2 B.Br C . H2O D.HOBr

(d)

Which of the following alkenes is expected to have the highest heat of hydrogenation (circle the correct answer (3 pts)? A.1-pentene B.trans-2-pentene C.cis-2-pentene D.2-methyl-2-butene

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4. (16 pts) (a) (9 pts) Compounds A is an alcohol of molecular formula C6H14O. On being heated with sulfuric acid, a major alkene B and a minor alkene C are formed. Ozonolysis, followed by treatment of the ozonide with dimethylsulfide, of major alkene B gives acetone (structure shown). What are the structures of compounds A and B and C. Briefly explain how you arrived at your answer (you can answer this by showing reactions). O
H3C CH3 acetone

Is acetone and aldehyde or ketone? ________________ (1 point)

(b) (6 pts) Outline a sequence of reactions that would be suitable for the preparation of the following compound from the indicated starting material and any needed reagents. The synthesis will require more than one step.

1-bromo-2-propanol from 2-propanol

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5 . Mechanisms (14 pts) (a) Provide a stepwise mechanism, using arrows to show electron movement, to account for the formation of the product in the following reaction. (6 pts)
IBr I Br

(b) Provide a stepwise mechanism, using arrows to show electron movement, to account for the formation of the products in the following reaction. (8 pts)
OH

H3O+