One of the chair conformers of cis-1,3-dimethylcyclohexane is 5.4 kcal/mol less stable

Draw a condensed structure and a skeletal structure for each of the following: a. sec-butyl tert-butyl ether e. 5-(1-methylethyl)nonane i. 3-ethoxy-2-methylhexane b. isoheptyl alcohol f. triethylamine j. 5-(1,2-dimethylpropyl)nonane c. sec-butylamine g. 4-(1,1-dimethylethyl)heptane k. 3,4-dimethyloctane d. isopentyl bromide h. 5,5-dibromo-2-methyloctane l. 5-isopentyldecane

List the following compounds from highest boiling to lowest boiling:

a. What is each compounds systematic name? b. Draw a skeletal structure for each condensed structure given and draw a condensed structure for each skeletal structure.

Which of the following represents a cis isomer?

a. How many primary carbons does each of the following compounds have? b. How many secondary carbons does each one have? c. How many tertiary carbons does each one have?

Which of the following conformers of isobutyl chloride is the most stable?

Draw a skeletal structure for an alkane that has a. six carbons, all secondary. b. eight carbons and only primary hydrogens. c. seven carbons with two isopropyl groups.

What is each compounds systematic name? a. CH3CH2CHCH3 NH2 e. CH3CHCH2CH2CH3 CH3 h. CH3CHCH2CH2CH2OH CH3 b. CH3CH2CHCH3 Cl f. CH3 CH3CHNH2 i. Br c. CH3CH2CHNHCH2CH3 CH3 g. CH2CH3 CH3C CH3 Br j. OH d. CH3CH2CH2OCH2CH3

Which has a. the higher boiling point: 1-bromopentane or 1-bromohexane? b. the higher boiling point: pentyl chloride or isopentyl chloride? c. the greater solubility in water: 1-butanol or 1-pentanol? d. the higher boiling point: 1-hexanol or 1-methoxypentane? e. the higher melting point: hexane or isohexane? f. the higher boiling point: 1-chloropentane or 1-pentanol? g. the higher boiling point: 1-bromopentane or 1-chloropentane? h. the higher boiling point: diethyl ether or butyl alcohol? i. the greater density: heptane or octane? j. the higher boiling point: isopentyl alcohol or isopentylamine? k. the higher boiling point: hexylamine or dipropylamine?

a. Draw Newman projections of the two conformers of cis-1,3-dimethylcyclohexane. b. Which of the conformers predominates at equilibrium? c. Draw Newman projections of the two conformers of the trans isomer. d. Which of the conformers predominates at equilibrium?

Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-inflammatory drugs (NSAIDs). Both are only slightly soluble in water, but one is a little more soluble than the other. Which of the drugs has the greater solubility in water?

Draw a picture of the hydrogen bonding in methanol.

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed. a. 4-bromo-3-pentanol e. 5-(2,2-dimethylethyl)nonane i. 1-bromo-4-pentanol b. 2,2-dimethyl-4-ethylheptane f. isopentylbromide j. 3-isopropyloctane c. 5-methylcyclohexanol g. 3,3-dichlorooctane k. 2-methyl-2-isopropylheptane d. 1,1-dimethyl-2-cyclohexanol h. 5-ethyl-2-methylhexane l. 2-methyl-N,N-dimethyl-4-hexanamine

Which of the following conformers has the highest energy (is the least stable)?

Give the systematic names for all alkanes with molecular formula C7H16 that do not have any secondary hydrogens.

Draw skeletal structures for the following: a. 5-ethyl-2-methyloctane c. 2,3,3,4-tetramethylheptane e. 2-methyl-4-(1-methylethyl)octane b. 1,3-dimethylcyclohexane d. propylcyclopentane f. 2,6-dimethyl-4-(2-methylpropyl)decane

For rotation about the C@3 C@4 bond of 2-methylhexane, do the following: a. Draw the Newman projection of the most stable conformer. b. Draw the Newman projection of the least stable conformer. c. About which other carboncarbon bonds may rotation occur? d. How many of the carboncarbon bonds in the compound have staggered conformers that are all equally stable?

Draw all the isomers that have molecular formula C5H11Br. (Hint: There are eight.) a. Give the systematic name for each of the isomers. b. Give a common name for each isomer that has a common name. c. How many of the isomers are primary alkyl halides? d. How many of the isomers are secondary alkyl halides? e. How many of the isomers are tertiary alkyl halides?

What is each compounds systematic name?

Draw the two chair conformers for each of the following and indicate which conformer is more stable: a. cis-1-ethyl-3-methylcyclohexane d. cis-1,2-diethylcyclohexane b. trans-1-ethyl-2-methylcyclohexane e. cis-1-ethyl-3-isopropylcyclohexane c. trans-1-ethyl-2-isopropylcyclohexane f. cis-1-ethyl-4-isopropylcyclohexane

Why are lower molecular weight alcohols more soluble in water than higher molecular weight alcohols?

a. Draw a potential energy diagram for rotation about the CC bond of 1,2-dichloroethane through 360, starting with the least stable conformer. The anti conformer is 1.2 kcal/mol more stable than a gauche conformer. A gauche conformer has two energy barriers, 5.2 kcal/mol and 9.3 kcal/mol. b. Draw the conformer that is present in greatest concentration. c. How much more stable is the most stable staggered conformer than the most stable eclipsed conformer? d. How much more stable is the most stable staggered conformer than the least stable eclipsed conformer?

For each of the following compounds, determine whether the cis isomer or the trans isomer is more stable.

How many ethers have molecular formula C5H12O? Draw their structures and give each a systematic name. What are their common names?

Draw the most stable conformer of the following molecule. (A solid wedge points out of the plane of the paper toward the viewer. A hatched wedge points back from the plane of the paper away from the viewer.)

What is each compounds systematic name?

Calculate the energy difference between the two chair conformers of trans-1,2-dimethylcyclohexane.

The most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with its five substituents all in equatorial

What is each compounds systematic name?

Explain the following: a. 1-Hexanol has a higher boiling point than 3-hexanol. b. Diethyl ether has very limited solubility in water, but tetrahydrofuran is completely soluble.

One of the chair conformers of cis-1,3-dimethylcyclohexane is 5.4 kcal/mol less stable than the other. How much steric strain does a 1,3-diaxial interaction between two methyl groups introduce into the conformer?

Bromine is a larger atom than chlorine, but the equilibrium constants in Table 3.9 indicate that a chloro substituent has a greater preference for the equatorial position than does a bromo substituent. Suggest an explanation for this fact.

Name the following compounds:

Using the data obtained in Problem 81, calculate the percentage of molecules of trans-1,2-dimethylcyclohexane that will have both methyl groups in equatorial positions.

Using the data obtained in Problem 85, calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?