Alkenes Alkynes Exercises (CH3)2CHCOOH.

Which of the following structures

1. In a Chain Reaction, the step where a reactive substance best represents A?
is consumed and another reactive substance is generated
is called A. D.
A. Key Chain
B. Chain Termination step
C. Chain Propagation B. E.
D. Chain Initiation
E. Jacky Chain C.
2. What product is formed via a hydride shift during the II. Short Answer Questions
following reaction? 1. What is Markovnikov’s rule? What is Saytzeff rule?
H Cl 2. What “new”, more stable, carbocation(s) may be formed
when the following carbocation undergoes spontaneous
rearrangement?
Cl
A. Cl C.
Cl 3. Propose a reasonable synthetic strategy for the synthesis
B. D. Cl of trans-6-methyl-3-heptene from 4-methyl-1-pentyne.
E. 3-Methylbutane Give structural details of all intermediates as well as the
3. What type of reactive intermediate is formed in the final product.
reaction of an alkene with HBr to give a bromoalkane? 4. Compound A, C10H18O undergoes dehydration using
A. alkyl radical C. carbanion sulfuric acid at 250oC to yield a mixture of two
B. cyclic bromonium ion D. carbocation alkenes, C10H16. The major alkene product, B, gives
E. carbene only cyclopentanone after ozone treatment followed by
4. What is the major organic product obtained from reduction with zinc in acetic acid. Identify A and B.
treating 1-Methylcyclohexene with Bromine (Br2)? 5. Draw/write the structure of the major product(s) and or
Br CH3 Br CH3 reactants in the reaction schemes given below.
Br excess HBr
(A) BH3 H2O2, OH-
(B)
COOH
A. C. + CO2
(C) (D)

Br CH3 CH3 5.1

Br Br
5.2
(C)
B. D.
E. Bromocyclopentane (A) 1. Hg(OAc)2, H2O
5. Which of the following statements is NOT TRUE about (B)
2. NaBH4, OH-
alkenes
A. Alkenes are unsaturated hydrocarbons HO
(E) (1) OsO4
B. Alkenes are nonpolar and hydrophobic (2) NaHSO3, H2O
(D)

C. Alkenes are polar and hydrophilic

D. Alkenes have densities lower than one. H3CO

E. Alkenes are nucleophilic.

6. What reagent may be used to convert 1-hexyne to 2- 6. The triene ester reacts with HBr to yield a rearranged
Bromo-1-hexene? alkyl bromide. Follow the flow of electrons as
A. H2/Lindlar catalyst C. excess HBr represented by the curved arrows, show the structure of
B. 1 equivalent Br2 D. NaBr the carbocation intermediate (A) in brackets, and show
E. 1 mol HBr the structure of the final product, (B).
7. The reaction of 3-octyne with two equivalents of Br2 CO2CH3

will produce what product?

-
A. 3,3-Dibromooctane ( A)
Br
( B)
B. 3,4-dibromooctane
C. 3,3,4,4-tetrabromooctane
D. 4,4,5,5-tetrabromooctane Br H

E. 3,4-dibromo-3-octene
8. What product will be generated when 1-heptyne is 7. Write the COMPLETE mechanisms for each of the
treated with H2O, HgSO4, H2SO4? reactions below. Use curved arrows to show electron
A. 2-Heptanol C. 1-Heptene movement.
B. 2-Heptanone D. 1-Hepten-2-ol (a) 3,3-dimethyl-1-pentene + HBr 3-Bromo-2,3-
E. 2-Heptyne dimethylpentane.
9. Which of the following statements is TRUE about (b) Methylcyclopentene + HBr/ROOR 1-Bromo-2-
alkynes? methylcyclopentane
A. Alkynes are saturated hydrocarbons.
B. Terminal alkynes are weakly acidic. (c) the keto-enol tautomerism in acidic solution below
C. Alkynes are polar. OH O
D. The triple bond in internal alkynes are found at the
+
end of the molecule. H
E. Alkynes can exhibit hydrogen bonding.
O
Br2/H2O CH2Br
10. An unknown compound, A, has the molecular formula
C7H12. On oxidation with hot aqueous potassium H2C=CHCH2CH2CH2OH
(d)
permanganate, A yields CH3CH2COOH and