Organic Chemistry

Problems 105

Key Terms

alcohol (p. 64)

alkane (p. 60)

alkyl halide (p. 64)

alkyl substituent (p. 63)

amine (p. 64)

angle strain (p. 92)

anti conformer (p. 90)

axial bond (p. 95)

banana bond (p. 92)

boat conformation (p. 97)

boiling point (bp) (p. 81)

chair conformation (p. 94)

cis fused (p. 104)

cis isomer (p. 100)

cis–trans isomers (p. 100)

common name (p. 63)

conformation (p. 88)

conformational analysis (p. 89)

conformer (p. 88)

constitutional isomers (p. 61)

cycloalkane (p. 71)

1,3-diaxial interaction (p. 98)

dipole–dipole interaction (p. 83)

eclipsed conformation (p. 89)

eclipsed conformer (p. 90)

equatorial bond (p. 95)

ether (p. 74)

flagpole hydrogen (p. 97)

functional group (p. 75)

gauche conformer (p. 90)

gauche interaction (p. 91)

geometric isomers (p. 100)

half-chair conformer (p. 97)

heat of formation (p. 96)

homolog (p. 60)

homologous series (p. 60)

hydrocarbon (p. 60)

hydrogen bond (p. 83)

induced-dipole–induced-dipole

interaction (p. 82)

IUPAC nomenclature (p. 63)

melting point (mp) (p. 86)

methylene group (p. 60)

Newman projection (p. 88)

packing (p. 86)

parent hydrocarbon (p. 67)

perspective formula (p. 88)

polarizability (p. 84)

primary alcohol (p. 75)

primary alkyl halide (p. 73)

primary amine (p. 77)

primary carbon (p. 64)

primary hydrogen (p. 65)

quaternary ammonium salt (p. 78)

ring flip (p. 96)

sawhorse projection (p. 88)

(CH 2 )

secondary alcohol (p. 75)

secondary alkyl halide (p. 73)

secondary amine (p. 77)

secondary carbon (p. 64)

secondary hydrogen (p. 65)

skeletal structure (p. 71)

skew-boat conformer (p. 97)

solubility (p. 86)

solvation (p. 86)

staggered conformation (p. 89)

staggered conformers (p. 90)

steric strain (p. 90)

straight-chain alkane (p. 60)

symmetrical ether (p. 74)

systematic nomenclature (p. 63)

tertiary alcohol (p. 75)

tertiary alkyl halide (p. 73)

tertiary amine (p. 77)

tertiary carbon (p. 65)

tertiary hydrogen (p. 65)

torsional strain (p. 89)

trans fused (p. 104)

trans isomer (p. 100)

twist-boat conformer (p. 97)

unsymmetrical ether (p. 74)

van der Waals forces (p. 82)

Problems

40. Write a structural formula for each of the following compounds:
    a. sec-butyl tert-butyl ether f. 4,5-diisopropylnonane k. 1-methylcyclopentanol
    b. isoheptyl alcohol g. triethylamine l. 3-ethoxy-2-methylhexane
    c. sec-butylamine h. cyclopentylcyclohexane m. 5-(1,2-dimethylpropyl)nonane
    d. neopentyl bromide i. 4-tert-butylheptane n. 3,4-dimethyloctane
    e. 1,1-dimethylcyclohexane j. 5,5-dibromo-2-methyloctane


41. Give the systematic name for each of the following compounds:

a. e. i.

b. f. j.

c. g. k.

d. h.

Br

(CH 3 CH 2 ) 4 C CH 3

CH 3 CH 2 CHOCH 2 CH 3 CH 3 OCH 2 CH 2 CH 2 OCH 3

CH 2 CH 2 CH 2 CH 3

CH 3 CHCH 2 CHCHCH 3

CH 3

CH 3 CH 3

OH

CH 3 CHCH 2 CHCH 2 CH 3 CH 2 CH 3

CH 3 OH

(CH 3 ) 3 CCH 2 CH 2 CH 2 CH(CH 3 ) 2

NCH 3

CH 3

CH 3 CHCH 2 CH 2 CHCH 2 CH 2 CH 3 BrCH 2 CH 2 CH 2 CH 2 CH 2 NHCH 2 CH 3

Br

CH 3

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