Using the data obtained in , calculate the percentage of

Draw a condensed structure and a skeletal structure for each of the following compounds: a. sec-butyl tert-butyl ether e. 5-(1,2-dimethylpropyl)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. 4-(1-methylethyl)nonane

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 given in the following list:

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 the structural formula 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?

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 would predominate at equilibrium? c. Draw Newman projections of the two conformers of the trans isomer. d. Which of the conformers would predominate at equilibrium?

Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-inl ammatory 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. isopentyl bromide 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 C 7 H 16 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 i 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 C 5 H 11 Br. ( 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 -isopropylcyclohexane e. cis -1-ethyl-3-isopropylcyclohexane c. trans -1-ethyl-2-methylcyclohexane 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 Ci C 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/mole. b. Draw the conformer that would be 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, is the cis isomer or the trans isomer more stable?

How many ethers have molecular formula C 5 H 12 O? 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.) CH3

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 i ve substituents all in equa torial positions. Draw the most stable conformer of glucose by putting the OH groups on the appropriate bonds in the structure on the right.

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 (23 kJ/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 a bromo substituent does. Suggest an explanation for this fact.

Name the following compounds:

Using the data obtained in Problem 78, 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 82, calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer would predominate at equilibrium?

Problem 10P a. Draw the 18 constitutional isomers with molecular formula C8H18. b. Give each isomer its systematic name. c. How many isomers have common names? d. Which isomers contain an isopropyl group? e. Which isomers contain a sec-butyl group? f. Which isomers contain a tert-butyl group?

What is each compound’s systematic name?

Draw the structure and give the systematic name of a compound with molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12}\) that has a. only primary and secondary hydrogens. b. only primary hydrogens. c. one tertiary hydrogen. d. two secondary hydrogens.

Give each of the following a systematic name, and indicate whether each is a primary, secondary, or tertiary alcohol:

Problem 23P Write the structures of all the tertiary alcohols with molecular formula C6H14O and give each a systematic name.

Give each of the following a systematic name, and indicate whether each is a primary, secondary, or tertiary alcohol:

List the compounds in each set from highest boiling to lowest boiling:

Rank the following compounds in each set from most soluble to least soluble in water: \(\text { b. } \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH} \quad \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl} \quad \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH} \quad \mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) Equation Transcription: Text Transcription: CH_3 CH_2 CH_2 OH CH_3 CH_2 CH_2 CH_2 Cl CH_3 CH_2 CH_2 CH_2 OH HOCH_2 CH_2 CH_2 OH

Problem 36P In which solvent would cyclohexane have the lowest solubility: 1-pentanol, diethyl ether, ethanol, or hexane?

Is each of the following a cis isomer or a trans isomer?

Problem 47P Which will have a higher percentage of the diequatorial-substituted conformer compared with the diaxial-substituted conformer, trans-1,4-dimethylcyclohexane or cis-1-tert-butyl-3-methylcyclohexane?

Problem 48P Draw the more stable chair conformer of ds-l-ethyl-2-methylcyclohexanc. ________________ b. Draw the more stable conformer of tram-1 -ethyl-2-methylcyclohexane. Which is more stable, cw-l-ethyl-2-methylcyclohexane or frans-l-ethyl-2- methylcyclohexane?

Problem 58P Draw the structural formula of 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 compound’s systematic name?

Problem 60P 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?

What is each compound’s systematic name?

Problem 71P 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-isopropylcyclohexane e. cis-1-ethyl-3-isopropylcyclohexane c. trans-1-ethyl-2-methylcyclohexane f. cis-1-ethyl-4-isopropylcyclohexane

Problem 72P Why are alcohols of lower molecular weight more soluble in water than those of higher molecular weight?

Problem 82P One of the chair conformers of cis-1,3-dimethylcyclohexane is 5.4 kcal/mol (23 kJ/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 a bromo substituent does. Suggest an explanation for this fact. Equation Transcription: Text Transcription: 3.9

Name the following compounds:

Problem 9UMM Build models of cis-1,2-dichlorocyclohexane and trans-1,2-dichlorocyclohexane. Build their mirror images. Show that the mirror images of the cis stereoisomers are superimposable but the mirror images of the trans stereoisomers are not superimposable.

Problem 11UMM Build two models of trans-2-pentene. To each model, add Br2 to opposite sides of the double bond, adding Br+ to the top of the double bond in one model and adding it to the bottom of the double bond in the other model, thereby forming the enantiomers shown on page 283. Rotate the models so they represent Fischer projections. Are they erythro or threo enantiomers? Compare your answer with that given on page 283.

Problem 12UMM See the box titled “Cyclic Alkenes” on page 280. Build models of the following compounds. Can any of them not be built? a. cis-cyclooctene b. trans-cyclooctene c. cis-cyclohexene d. trans-cyclohexene

a. How many hydrogens does an alkane with 17 carbons have? b. How many carbons does an alkane with 74 hydrogens have?

Problem 2P Draw the structures of octane and isooctane.

How many hydrogens are attached to each of the indicated carbons in morphine?

Convert the following condensed structures into skeletal structures:

Convert the structures in Problem \(11\) into skeletal structures. Equation Transcription: Text Transcription: 11

Are the following compounds primary, secondary, or tertiary?

Give a systematic name and a common name (if it has one) for each of the following amines and indicate whether each is a primary, secondary, or tertiary amine:

Draw the structure for each of the following amines: a. 2-methyl- N -propyl-1-propanamine b. N -ethylethanamine c. 5-methyl-1-hexanamine d. methyldipropylamine e. N , N -dimethyl-3-pentanamine f. Cyclohexylethylmethylamine

a. Draw all the staggered and eclipsed conformers that result from rotation about the \(C-2-C-3\) bond of pentane. b. Draw a potential-energy diagram for rotation about the \(C-2-C-3\) bond of pentane through \(360^{\circ}\), starting with the least stable conformer. Equation Transcription: ° Text Transcription: C-2-C-3 360 degree

Convert the following Newman projections to skeletal structures and name them.

Problem 39P Using Newman projections, draw the most stable conformer for each of the following: a. 3-methylpentane, viewed along the C-2-C-3 bond b. 3-methylhexane, viewed along the C-3-C-4 bond c. 3,3-dimethylhexane, viewed along the C-3-C-4 bond

Problem 49P For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers will be both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers: a. cis-1,2- b. trans-1,2- c. cis-1,3- d. trans-1,3- e. cis-1,4- f. trans-1,4-

Problem 50P a. Draw Newman projections of the two conformers of cis-1,3-dimethylcyclohexane. b. Which of the conformers would predominate at equilibrium? c. Draw Newman projections of the two conformers of the trans isomer. d. Which of the conformers would predominate at equilibrium?

a. Calculate the energy difference between the two chair conformers of trans-1,4-dimethylcyclohexane. b. What is the energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?

Problem 61P a. Draw Newman projections of the two conformers of cis-1,3-dimethylcyclohexane. b. Which of the conformers would predominate at equilibrium? c. Draw Newman projections of the two conformers of the trans isomer. d. Which of the conformers would predominate at equilibrium?

Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-inflammatory drugs (\(\text { NSAIDS }\)). 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? Equation Transcription: Text Transcription: NSAIDs

Draw a picture of the hydrogen bonding in methanol.

Problem 73P a. Draw a potential energy diagram for rotation about the C-C bond of 1,2-dichloroethane through 360o, 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 would be 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?

Problem 75P How many ethers have molecular formula C5H12O? Draw their structures and name them.

For each of the following compounds, is the \(\text { cis }\) isomer or the trans isomer more stable? Equation Transcription: Text Transcription: cis

Problem 85P Using the data obtained in Problem 78, calculate the percentage of molecules of trans-1,2-dimethylcyclohexane that will have both methyl groups in equatorial positions. Reference: Problem 78: Calculate the energy difference between the two chair conformers of trans-1,2-dimethylcyclohexane.

Problem 86P Using the data obtained in Problem 82, calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer would predominate at equilibrium? Reference: Problem 82: One of the chair conformers of cis-1,3-dimethylcyclohexane is 5.4 kcal/mol (23 kJ/mol) less stable than the other. How much steric strain does a 1,3-diaxial interaction between two methyl groups introduce into the conformer?

Problem 1UMM Build a model of each of the enantiomers of 2-bromobutane (see page 153). a. Try to superimpose them. b. Turn them so you can see that they are mirror images. c. Which one is (R)-2-bromobutane?

Name each of the following:

Problem 4P Draw the structure and give the systematic name of a compound with molecular formula C5H12 that has a. one tertiary carbon. b. no secondary carbons.

Problem 5P Draw the structures and name the four constitutional isomers with molecular formula C4H9Br.

Problem 16P Draw a condensed and a skeletal structure for each of following: a. 3,4-diethyl-2-methylheptane b. 2,2,5-trimethylhexane

What is each compound’s systematic name?

Give two names for each of the following alkyl halides and indicate whether each is primary, secondary, or tertiary:

For each of the following, give the systematic name and the common name (if it has one), and then indicate whether it is a primary, secondary, or tertiary amine:

Problem 29P Predict the approximate size of the following bond angles. (Hint: See Sections 1.11 and 1.12.) a. the C-O-C bond angle in an ether b. the C-N-C bond angle in a secondary amine c. the C-O-H bond angle in an alcohol d. the C-N-C bond angle in a quaternary ammonium salt

Problem 30P What is the smallest alkane that is a liquid at room temperature?

The bond angles in a regular polygon with \(n\) sides are equal to \(180^{\circ}-\frac{360 \text { degrees }}{n}\) a. What are the bond angles in a regular octagon? b. What are the bond angles in a regular nonagon? Equation Transcription: ° Text Transcription: n 180 degrees - 360 degrees/n

Verify the strain energy shown in Table \(3.8\) for cycloheptane. Equation Transcription: Text Transcription: 3.8

The effectiveness of a barbiturate as a sedative is related to its ability to penetrate the nonpolar membrane of a cell. Which of the following barbiturates would you expect to be the more effective sedative?

Problem 52P Draw a condensed structure and a skeletal structure for each of the following compounds: 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. 4-(1-methylethyl)nonane

List the following compounds from highest boiling to lowest boiling:

a. What is each compound’s systematic name? b. Draw a skeletal structure for each condensed structure given, and draw a condensed structure for each skeletal structure given in the following list:

Problem 64P 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. isopentyl bromide 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 \(C_{7} H_{16}\) that do not have any secondary hydrogens. Equation Transcription: Text Transcription: C_7 H_16

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 compound’s systematic name?

Problem 78P Calculate the energy difference between the two chair conformers of trans-1,2-dimethylcyclohexane.

Problem 2UMM Build models of the stereoisomers of 3-chloro-2-butanol that are labeled 1 and 2 shown on the top of page 165. a. Where are the Cl and OH substituents (relative to each other) in the Fischer projection? (Recall that in a Fischer projection, the horizontal lines represent bonds that point out of the plane of the paper toward the viewer, whereas the vertical lines represent bonds that point back from the plane of the paper away from the viewer.) b. Where are the Cl and OH substituents (relative to each other) in the most stable conformer (considering rotation about the C-2—C-3 bond)?

Problem 4UMM Build a model of each of the four stereoisomers of 2,3-dibromopentane. Why does 2,3-dibromopentane have four stereoisomers, whereas 2,3-dibromobutane has only three?

Problem 5UMM Build a model of (S)-2-pentanol.

Problem 6P Which of the following statements can be used to prove that carbon is tetrahedral? a. Methyl bromide does not have constitutional isomers. b. Tetrachloromethane does not have a dipole moment. c. Dibromomethane does not have constitutional isomers.

Problem 7P Which of the following statements can be used to prove that carbon is tetrahedral? a. Methyl bromide does not have constitutional isomers. b. Tetrachloromethane does not have a dipole moment. c. Dibromomethane does not have constitutional isomers. Draw the structure for each of the following compounds: a. isopropyl alcohol c. sec-butyl iodide e. tert-butylamine b. isopentyl fluoride d. tert-pentyl alcohol f. n-octyl bromide

Name the following compounds: a. \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) b. \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) d. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

Problem 19E Draw the structures and provide systematic names for parts a , b, and c by substituting a chlorine for a hydrogen of methylcyclohexane: a. a primary alkyl halide b. a tertiary alkyl halide c. three secondary alkyl halides

a. What is each ether’s systematic name? 1. \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) 2. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) b. Do all of these ethers have common names? c. What are their common names? Equation Transcription: Text Transcription: CH_3 OCH_2 CH_3 CH_3 CH_2 OCH_2 CH_3

Problem 21P Draw the structures of a homologous series of alcohols with the OH group on a terminal carbon and that have from one to six carbons, and then give each of them a common name and a systematic name.

a.) Which of the following compounds will form hydrogen bonds between its molecules? 1. \(CH_3CH_2OCH_2CH_2OH\) 4. \(CH_3CH_2CH_2NHCH_3\) 2. \(CH_3CH_2N(CH_3)_2\) 5. \(CH_3CH_2CH_2COOH\) 3. \(CH_3CH_2CH_2CH_2Br\) 6. \(CH_3CH_2CH_2CH_2F\) b.) Which of the preceding compounds will form hydrogen bonds with a solvent such as ethanol?

Problem 32P Explain why a. H2O (100 °C) has a higher boiling point than CH3OH (65 °C). b. H2O (100 °C) has a higher boiling point than NH3 (-33 °C). c. H2O (100 °C) has a higher boiling point than HF (20 °C). d. HF (20 °C) has a higher boiling point than NH3 (-33 °C).

List the following compounds from highest boiling to lowest boiling:

Draw \(1,2,3,4,5,6\)-hexachlorocyclohexane with a. all the chloro groups in axial positions. b. all the chloro groups in equatorial positions Equation Transcription: Text Transcription: 1, 2, 3, 4, 5, 6

Problem 44P The chair conformer of fluorocyclohexane is 0.25 kcal/mol more stable when the fluoro substituent is in an equatorial position than when it is in an axial position. How much more stable is the anti conformer than a gauche conformer of 1-fluoropropane considering rotation about the C-1-C-2 bond?

Using the data in Table \(3.9\) , calculate the percentage of molecules of cyclohexanol that have the \(O H\) group in an equatorial position at \(25^{\circ} \mathrm{C}\). Equation Transcription: ° Text Transcription: 3.9 OH 25 degrees C

Which of the following represents a \(\text { cis }\) isomer? Equation Transcription: Text Transcription: cis

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 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 carbon-carbon bonds may rotation occur? d. How many of the carbon-carbon bonds in the compound have staggered conformations that are all equally stable?

Problem 69P 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?

The most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with its i ve substituents all in equatorial positions. Draw the most stable conformer of glucose by putting the \(O H\) groups on the appropriate bonds in the structure on the right. Equation Transcription: Text Transcription: OH

What is each compound’s 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. Equation Transcription: Text Transcription: 1 3

Build a model of (2S,3S)-3-bromo-2-butanol. Rotate the model so its conformation is displayed as a Fischer projection. Compare this structure with that shown on page 174.

a. Build a model of \(\text { cis }\) -\(1\)-bromo-\(4\)-chlorocyclohexane. Build its mirror image. Are they superimposable? b. Build a model of \(\text { cis }\) -\(1\)-bromo-\(2\)-chlorocyclohexane. Build its mirror image. Are they superimposable? Equation Transcription: Text Transcription: cis 1 4 2

Problem 8UMM a. Build a model of cis-1-bromo-4-chlorocyclohexane. Build its mirror image. Are they superimposable? b. Build a model of cis-1-bromo-2-chlorocyclohexane. Build its mirror image. Are they superimposable?