Assignment 3 - organic chemistry PDF

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CHM2210 Assignment 3 1) Which of the statements below accurately describe(s) alkanes? A) Alkanes are hydrocarbons which contain only single bonds. B) Alkanes belong to the class of unsaturated hydrocarbons. C) Alkanes are the simplest and least reactive class of organic compounds. D) both A and B E) both A and C 2) Which of the following types of hydrocarbons is(are) saturated? A) alkanes B) alkenes C) alkynes D) aromatics E) All of the above are saturated. 3) The structure below is a potent analgesic agent (pain reliever) (J. Med. Chem., 2009, 5685). How many secondary carbons are in this structure?

4) How many methylene groups are present in 2,4-dimethylhexane? 5) How many secondary (2°) carbons are found in 5-ethyl-3,3,4-trimethylheptane? 6) Provide the name of the compound below.

7) Provide an acceptable name for (CH3CH2CH2)3CH. 8) Provide the name of the compound below.

9) Provide an acceptable name for the alkane shown below. CH3CH2CH2CH2CH2CH3

10) Provide an acceptable name for the alkane shown below.

11) Draw an acceptable structure for 4-tert-butyloctane. 12) Draw an acceptable structure for 3-ethyl-3-methylhexane. 13) Draw an acceptable structure for 4-isopropyl-2-methylheptane. 14) Name the haloalkane shown.

15) Provide an acceptable name for the following compound.

16) Provide an acceptable name for the [(CH3)3C]2CHCH3.

17) Provide an acceptable name for the alkane shown below.

18) Provide an acceptable name for the alkane shown below.

19) Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane. 20 )Provide an acceptable name for the alkane shown below.

21) Name the alkane shown.

22) Provide the name of the compound shown.

23) Why are alkanes described as hydrophobic? 24) Which intermolecular force is primarily responsible for the interactions among alkane molecules?

25) By using the appropriate molecular formulas, write a balanced equation which describes the complete combustion of cyclohexane.

26) When a mole of decane undergoes complete combustion, how many moles of water are formed? 27) By using the appropriate molecular formulas, write a balanced equation which describes the complete combustion of nonane. 28) The structures below are:

A) not isomers. B) conformational isomers. C) cis-trans isomers. D) structural isomers. E) both B and D 29) Draw a Newman projection of the most stable conformation of 2-methylpropane. 30) Use a sawhorse structure to depict the eclipsed conformer of ethane. 31) Draw the Newman projection of the highest energy conformation that results from rotation about the C2-C3 bond of 2,2-dimethylbutane. 32) Draw the Newman projection of the lowest energy conformation that results from rotation about the C2-C3 bond of 2-methylbutane.

33) Consider rotation about the C3-C4 bond of hexane, and draw the Newman projection for the most stable conformation.

34) Arrange the following conformers of butane in order of energy, lowest to highest: eclipsed, totally eclipsed, gauche, and anti. 35) Without any change in conformation, translate the Newman projection shown below to a perspective structure.

36 )In a Newman projection, siting down the C3-C4 bond, draw the structure below in its

most stable conformation.

37 )Give the IUPAC name for the cycloalkane shown below.

38) Give the IUPAC name for the cycloalkane shown below.

39) Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the equatorial hydrogens (He). 40) Consider the equilibrium shown below. When one looks at the equilibrium where X

= CH3 and the one where X = CH(CH3)2, how do the values of the equilibrium constants (Ks) compare?

A) The Ks are equal. B) The K where X = CH3 is greater. C) The K where X = CH(CH3)2 is greater. D) The Ks differ only slightly and are both less than 1.

41 )In the lowest energy chair conformation of cis-1,3-dimethylcyclohexane, how many axial positions are occupied by hydrogen atoms? 42 )In the lowest energy conformation of the compound below, how many alkyl

substituents are equatorial?

43 )In the lowest energy conformation of the compound below, how many alkyl

substituents are axial?

44) Draw the most stable conformation of cis-1-t-butyl-4-methylcyclohexane. 45 )Draw the chair conformation of the cyclohexane derivative shown.

46) Draw the most stable conformation of cis-1,4-dipropylcyclohexane. 47) Draw the most stable conformation of trans-1,4-dipropylcyclohexane. 48) With each structure below drawn in its most stable chair conformation, identify the sequence that ranks the structures in order of increasing stability.

49) Provide an acceptable name for the compound below.

50) Provide an acceptable structure for spiro [4.4]nonane. 51) Draw the most stable conformation of trans-decalin...