351 C4 Smith key

351 C4 Smith key - Chemistry 351 Fall 2008 Chapter 4 1...

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Unformatted text preview: Chemistry 351 Fall 2008 Chapter 4 1. Assign the IUPAC name to the following structures. 0k 1,: _Jhfigg~mefi%fimfilm c, 2&4 ' wfrm—MUEWM lo‘ 1+. 155%-! l 2» chlwlhfiéoado lac/(Cam, 2. Draw and derive IUPAC names for the constitutional isomers of C7H16 that have no tertiary carbons. higher, 3} 2 'd/t’mfiji’l/fPQw-lflm 315v dirwmfiewhiaw 3. Heats of combustion (the amount of energy given off in combustion) is a measure of the relative stability of isomeric alkanes. A more branched isomer has a smaller heat of combustion and is more stable than a less branched isomer. Circle the isomer below that gives off less heat when burned. 2-methylpentane 2 3-dimethylbutane 4. Determine whether the following reactions are oxidation, reduction, or neither. a. 0 on r ‘ 0/ Wow H20 b. - W —————~'{B' A/Y {RE/(Wm r 5. Using Newman projections, draw the most stable conformer for the following: a. 3-methylhexane, considering rotation about the C-3 — C—4 bond. H , , /\%+\/ R @ Okla—k; an‘i’l p€é1€iavia ,’ bell/06M» Ciiz . CH5 H 6%; @7345 W”? b. 3-methylpentane, considering rotation about the C-2 - C-3 bond. /\|/\ m 3- am‘i‘l v—I Pia M r +0 H l H ~25 C 3 m 6. Draw the most stable conformer of: a. cis—l -bromo—3 -chlorocyclohexane Br {$7 b. cis— l -ethyl-4-methylcyclohexane M 0W5 0% c. trans-l -i0do-2-isopropylcyclohexane 7. Name and describe three types of strain that contribute to the overall energy of a q ’ mm W Mm. . re tram cam“ gems W ectng ‘ 3*me o a Ca’tcflm bib 1” S W‘ E3 VLC’ 5' “3\' H kxD/nm CL S gfiz ‘ W abgfij’is OULVL 2, Ont-1&2 3 W ’1 S I [3% _ a. . _ m {am-£23 ow +72 Pm” W) A 8. Draw 1,2,4-trlmethylhexane With all 1 methy groups ax1al on the cyclohexane (N S template given below. New draw the other chair conformer obtained from the ring flip. 99% I __. _ / cu gnaw 5 can CR2» 3 Finally, draw 1,2,4—trimethylhexane with all its methyl groups equatorial on the cyclohexane template given belowl"r What is the relationship between your ring flip structure above and this structure? “TWU%3 are veal iSafxwihnFXnnggkgf cw 0+5 “Wye mtxlcok i1 Marta cute) 5”5 th. VVthvev’ llVg:§§S. fllflg {Edtéflkg slemo'Emmrg MD/U ‘ U094 Lxfl Lea We IA. ll S’lb—vl 05f [Om SMW Cé'wlown Inn balk lemda'fe S. Ch’ 93‘ 9. Glucose is a sugar molecule that is a heterocyclic compound. A planar representation of glucose is given below. Draw the chair conformer where all of its substituents are in the equatorial position using the template given below. HOCH2 O Chlon HO OH HO 0 HO /OH HO HO OH ...
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351 C4 Smith key - Chemistry 351 Fall 2008 Chapter 4 1...

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