TUTORIAL PROBLEMS, 2013/2014 ChE 153 Organic Chemistry for Engineers

KNUST- CHEMICAL ENGINEERING

Write structural formulas for each of the following: 1-Bromo-6-methylcyclohexene 4-Methyl-4-penten-2-ol (Z)-3-Methyl-2-hexene Vinylcycloheptane 1,1-Diallylcyclopropane trans-1-Isopropenyl-3-methylcyclohexane cis-3-Octene

Write a structural formula or build a

molecular model and give a correct IUPAC

name for each alkene of molecular

formula C7H14 that has a tetrasubstituted

double bond.

Que 3. Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a)Hydrogen chloride (b) Hydrogen bromide (c) Hydrogen bromide in the presence of peroxides (d) Hydrogen iodide (e) Dilute sulfuric acid (f ) Diborane in diglyme, followed by basic hydrogen peroxide (g) Bromine in carbon tetrachloride (h) Bromine in water (i ) Peroxyacetic acid (j) Ozone

Que 4. Match the following alkenes with the appropriate heats of hydrogenation: (a) 1-Pentene (b) (E)-4,4-Dimethyl-2-pentene (c) (Z)-4-Methyl-2-pentene (d) (Z)-2,2,5,5-Tetramethyl-3-hexene (e) 2,4-Dimethyl-2-pentene Heats of hydrogenation in kJ/mol (kcal/mol): 151(36.2); 122(29.3); 114(27.3); 111(26.5); 105(25.1).

Que 5. Reaction of 3,3-dimethyl-1-butene with hydrogen iodide yields two compounds A and B, each having the molecular formula C6H13I, in the ratio A:B 90:10. Compound A, on being heated with potassium hydroxide in n-propyl alcohol, gives only 3,3-dimethyl-1-butene. Compound B undergoes elimination under these conditions to give 2,3-dimethyl-2-butene as the major product. Suggest structures for compounds A and B, and write a reasonable mechanism for the formation

Que 6. Specify reagents suitable for converting 3-ethyl-2-pentene to each of the following: (a) 2,3-Dibromo-3-ethylpentane (b) 3-Chloro-3-ethylpentane (c) 2-Bromo-3-ethylpentane (d) 3-Ethyl-3-pentanol (e) 3-Ethyl-2-pentanol (f ) 3-Ethyl-2,3-epoxypentane (g) 3-Ethylpentane

Consider the following alkene:

(a) What is the molecular formula of this alkene? (b) What is its IUPAC name? (c) How many carbon atoms are sp2-hybridized in this alkene? How many are sp3hybridized? (d) How many _ bonds are of the sp2sp3 type? How many are of the sp3sp3 type?

Determine the configuration of each of the following alkenes as Z or E as appropriate:

Write structural formulas or build molecular models and give the IUPAC names for all the alkenes of molecular formula C6H12 that contain a trisubstituted double bond.

Name the compounds below.

When the alkene 3,3-dimethylbutene is treated with hydrogen iodide, there is obtained a mixture of products; 3-iodo2,2-dimethylbutane and 3-iodo2,3dimethylbutane. Write the eqn. for the reaction. What is the implication of the formation of the 2nd product. Propose a possible mechanism for the reaction.

When optically pure 2,3-dimethyl-2pentanol was subjected to dehydration, a mixture of two alkenes was obtained. Hydrogenation of this alkene mixture gave 2,3-dimethylpentane. What were the two alkenes formed in the elimination reaction, and what were the relative amounts of each?

Are the molecules shown below chiral or achiral?

Are the molecules shown below chiral or achiral? Name the second compond.

Is the molecule shown below chiral or achiral?

Label each carbon atom as R or S

Label each carbon atom as R or S

How many asymmetric carbons are in the compound below.

How many asymmetric carbons are in the compound shown below?