Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism Draw

Using the general molecular formula for alkanes: (a) Predict the molecular formula of the straight-chain alkane. (b) Predict the molecular formula of 4,6-diethyl-12-(3,5-dimethyloctyl)triacontane, an alkane containing 44 carbon atoms.

Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order.

Write structures for the following compounds. (a) 3-ethyl-4-methylhexane (b) 3-ethyl-5-isobutyl-3-methylnonane (c) 4-tert-butyl-2-methylheptane (d) 5-isopropyl-3,3,4-trimethyloctane

Provide IUPAC names for the following compounds.

All of the following names are incorrect or incomplete. In each case, draw the structure (or a possible structure) and name it correctly. (a) 2-methylethylpentane (b) 2-ethyl-3-methylpentane (c) 3-dimethylhexane (d) 4-isobutylheptane (e) 2-bromo-3-ethylbutane (f) 2-diethyl-3-methylhexane

Give structures and names for: (a) the five isomers of C6H14 (b) the nine isomers of C7H16

Draw the structures of the following groups, and give their more common names. (a) the (1-methylethyl) group (b) the (2-methylpropyl) group (c) the (1-methylpropyl) group (d) the (1,1-dimethylethyl) group (e) the (3-methylbutyl) group, sometimes called the isoamyl group

Draw the structures of the following compounds. (a) 4-(1,1-dimethylethyl)octane (b) 5-(1,2,2-trimethylpropyl)nonane (c) 3,3-diethyl-4-(2,2-dimethylpropyl)octane

Without looking at the structures, give molecular formulas for the compounds in Problem 3-8 (a) and (b). Use the names of the groups to determine the number of carbon atoms, then use the 12n+22 rule.

List each set of compounds in order of increasing boiling point. (a) hexane, octane, and decane (b) octane, and CH 1CH323CC1CH323 3CH2C1CH322CH2CH2CH3

Draw a graph, similar to Figure 3-9, of the torsional strain of 2-methylpropane as it rotates about the bond between C1 and C2. Show the dihedral angle and draw a Newman projection for each staggered and eclipsed conformation.

Draw a graph, similar to Figure 3-11, of the torsional energy of 2-methylbutane as it rotates about the bond

Draw a perspective representation of the most stable conformation of 3-methylhexane.

Give IUPAC names for the following compounds.

Draw the structure and give the molecular formula for each of the following compounds. (a) 1-ethyl-3-methylcycloheptane (b) isobutylcyclohexane (c) cyclopropylcyclopentane (d) 3-ethyl-1,1-dimethylcyclohexane (e) 3-ethyl-2,4-dimethylhexane (f) 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane

Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers. (a) 3-ethyl-1,1-dimethylcyclohexane (b) 1-ethyl-3-methylcycloheptane (c) 1-ethyl-3-methylcyclopentane (d) 1-cyclopropyl-2-methylcyclohexan

Give IUPAC names for the following cycloalkanes. CH3 H H CH2CH2CH3 (a) (b) H

The heat of combustion of cis-1,2-dimethylcyclopropane is larger than that of the trans isomer. Which isomer is more stable? Use drawings to explain this difference in stability

trans-1,2-Dimethylcyclobutane is more stable than cis-1,2-dimethylcyclobutane, but cis-1,3- dimethylcyclobutane is more stable than trans-1,3-dimethylcyclobutane. Use drawings to explain these observations.

The cyclohexane chair just drawn has the headrest to the left and the footrest to the right. Draw a cyclohexane chair with its axial and equatorial bonds, having the headrest to the right and the footrest to the left.

Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groups (a) in axial positions. (b) in equatorial positions

Draw a Newman projection, similar to Figure 3-25, down the bond in the equatorial conformation of methylcyclohexane. Show that the equatorial methyl group is also anti to C5. (Using your models will help.)

Table 3-6 shows that the axialequatorial energy difference for methyl, ethyl, and isopropyl groups increases gradually: 7.6, 7.9, and 8.8 kJ mol (1.8, 1.9, and 2.1 kcal mol). The tertbutyl group jumps to an energy difference of 23 kJ mol (5.4 kcal mol), over twice the value for the isopropyl group. Draw pictures of the axial conformations of isopropylcyclohexane and tert-butylcyclohexane, and explain why the tert-butyl substituent experiences such a large increase in axial energy over the isopropyl group.

Draw the most stable conformation of: (a) ethylcyclohexane (b) 3-isopropyl-1,1-dimethylcyclohexane (c) cis-1-tert-butyl-4-isopropylcyclohexane

(a) Draw both chair conformations of cis-1,4-dimethylcyclohexane, and determine which conformer is more stable. (b) Repeat for the trans isomer. (c) Predict which isomer (cis or trans) is more stable.

Use your results from Problem 3-25 to complete the following table. Each entry shows the positions of two groups arranged as shown. For example, two groups that are trans on adjacent carbons (trans-1,2) must be both equatorial (e,e) or both axial (a,a).

Draw the two chair conformations of each of the following substituted cyclohexanes. In each case, label the more stable conformation. (a) cis-1-ethyl-2-methylcyclohexane (b) trans-1,2-diethylcyclohexane (c) cis-1-ethyl-4-isopropylcyclohexane (d) trans-1-ethyl-4-methylcyclohexane

Name the following compounds. Remember that two up bonds are cis; two down bonds are cis; one up bond and one down bond are trans.

Draw the most stable conformation of: (a) cis-1-tert-butyl-3-ethylcyclohexane (b) trans-1-tert-butyl-2-methylcyclohexane (c) trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane

Name the following compounds.

Use your models to do a chairchair interconversion on each ring of the conformation of cisdecalin shown in Figure 3-27. Draw the conformation that results.

(a) There are eighteen isomeric alkanes of molecular formula C8H18. Draw and name any eight of them. (b) Draw and name the six isomeric cyclopentanes of molecular formula . These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism

Which of the following structures represent the same compound? Which ones represent different compounds?

Draw the structure that corresponds with each name. (a) 3-ethyloctane (b) 4-isopropyldecane (c) sec-butylcycloheptane (d) 2,3-dimethyl-4-propylnonane (e) 2,2,4,4-tetramethylhexane (f) trans-1,3-diethylcyclopentane (g) cis-1-ethyl-4-methylcyclohexane (h) isobutylcyclopentane (i) tert-butylcyclohexane (j) pentylcyclohexane (k) cyclobutylcyclohexane (l) cis-1-bromo-3-chlorocyclohexane

Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description. (a) an isopropylheptane (b) a diethyldecane (c) a cis-diethylcyclohexane (d) a trans-dihalocyclopentane (e) a (2,3-dimethylpentyl)cycloalkane (f) a bicyclononane

Write structures for a homologous series of alcohols having from one to six carbons.

Give the IUPAC names of the following alkanes. (a) CH3C1CH322CH1CH2CH32CH2CH2CH1CH322 1ROH2 (b) CH3CH2 CH CHCH3 CH2CH2 CH3 CH CHCH3 C

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentane along the bond. Place C2 in front, represented by three bonds coming together in a Y shape, and C3 in back, represented by a circle with three bonds pointing out from it. Define the dihedral angle as the angle between the methyl group on the front carbon and the ethyl group on the back carbon. Begin your graph at the 0 dihedral angle, and show the Newman projection and the approximate energy at each 60 of rotation. Indicate which conformations are the most stable (lowest energy) and the least stable (highest energy).

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly. (a) 2-ethylpentane (b) 3-isopropylhexane (c) 5-chloro-4-methylhexane (d) 2-dimethylbutane (e) 2-cyclohexylbutane (f) 2,3-diethylcyclopentane

In each pair of compounds, which compound has the higher boiling point? Explain your reasoning. (a) octane or 2,2,3-trimethylpentane (b) nonane or 2-methylheptane (c) 2,2,5-trimethylhexane or nonane

There are eight different five-carbon alkyl groups. (a) Draw them. (b) Give them systematic names. (c) In each case, label the degree of substitution (primary, secondary, or tertiary) of the head carbon atom, bonded to the main chain.

Use a Newman projection, about the indicated bond, to draw the most stable conformer for each compound. (a) 3-methylpentane about the bond (b) 3,3-dimethylhexane about the bond

(a) Draw the two chair conformations of cis-1,3-dimethylcyclohexane and label all the positions as axial or equatorial. (b) Label the higher-energy conformation and the lower-energy conformation. (c) The energy difference in these two conformations has been measured to be about 23 kJ (5.4 kcal) per mole. How much of this energy difference is due to the torsional energy of gauche relationships? (d) How much energy is due to the additional steric strain of the 1,3-diaxial interaction?

Draw the two chair conformations of each compound and label the substituents as axial and equatorial. In each case, determine which conformation is more stable. (a) cis-1-ethyl-2-isopropylcyclohexane (b) trans-1-ethyl-2-isopropylcyclohexane (c) cis-1-ethyl-3-methylcyclohexane (d) trans-1-ethyl-3-methylcyclohexane (e) cis-1-ethyl-4-methylcyclohexane (f) trans-1-ethyl-4-methylcyclohexane

Using what you know about the conformational energetics of substituted cyclohexanes, predict which of the two decalin isomers is more stable. Explain your reasoning.

Convert each Newman projection to the equivalent lineangle formula, and assign the IUPAC name

Draw Newman projections along the bond to show the most stable and least stable conformations of 3-ethyl2,4,4-trimethylheptane.

Conformational studies on ethane-1,2-diol ( ) have shown the most stable conformation about the central bond to be the gauche conformation, which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation. Draw Newman projections of these conformers and explain this curious result

Conformational studies on ethane-1,2-diol ( ) have shown the most stable conformation about the central bond to be the gauche conformation, which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation. Draw Newman projections of these conformers and explain this curious result