Organic Chemistry

Problems 261

25. Give the systematic name for each of the following structures:

a. c.

b. d.

26. What reagents could be used to carry out the following syntheses?


27. Al Kyne was given the structural formulas of several compounds and was asked to give them systematic names. How many did Al
    name correctly? Correct those that are misnamed.
    a. 4-ethyl-2-pentyne c. 2-methyl-3-hexyne
    b. 1-bromo-4-heptyne d. 3-pentyne


28. Draw the structures and give the common and systematic names for the seven alkynes with molecular formula


29. How could the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbon atoms as the
    desired product?

a. c.

b. d.

30. What reagents would you use for the following syntheses?
    a. (Z)-3-hexene from 3-hexyne
    b. (E)-3-hexene from 3-hexyne
    c. hexane from 3-hexyne


31. What is the molecular formula of a hydrocarbon that has 1 triple bond, 2 double bonds, 1 ring, and 32 carbons?


32. What will be the major product of the reaction of 1 mol of propyne with each of the following reagents?
    a. HBr (1 mol) g.
    b. HBr (2 mol) h. excess
    c. i. catalyst
    d. j. sodium in liquid ammonia
    e. aqueous k. sodium amide
    f. disiamylborane followed by l. product of Problem k followed by 1-chloropentane


33. Answer Problem 32, using 2-butyne as the starting material instead of propyne.


34. a. Starting with isopropylacetylene, how could you prepare the following alcohols?
    
    
    1. 2-methyl-2-pentanol
    
    
    2. 4-methyl-2-pentanol
       b. In each case a second alcohol would also be obtained. What alcohol would it be?
    
    
    
    


35. How many of the following names are correct? Correct the incorrect names.
    a. 4-heptyne d. 2,3-dimethyl-5-octyne
    b. 2-ethyl-3-hexyne e. 4,4-dimethyl-2-pentyne
    c. 4-chloro-2-pentyne f. 2,5-dimethyl-3-hexyne

H 2 O 2 >HO-

H 2 SO 4 , HgSO 4

Br 2 (2 mol)>CH 2 Cl 2

Br 2 (1 mol)>CH 2 Cl 2 H 2 >Lindlar

H 2 >Pt

HBr+H 2 O 2

CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CH 2 CH 2 Br

O

CH 3 CH 2 CH 2 CCH 2 CH 2 CH 2 CH 3

O

CH 3 CH 2 CH 2 CH 2 CH

C 6 H 10.

RCH 2 CH 3 RCH 2 CH 2 Br

Br

RCHCH 3

Br

Br

Br

RCCH 3 O

RCCH 3

O

RCH 2 CH

RC CH

RCH CH 2

RC CH 2

Cl CH 3

CH 3 CHCH 2 C CCHCH 3

CH 2 CH 2 CH 3

CH 3 C CCH 2 CHCH 3

CH 3

CH 3

CH 3 C CCH 2 CCH 3

Br

CH 3 C CCH 2 CHCH 3

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