PROBLEMS. Selctoin-huper nd end chaptr problems have brief arses provided in pen 8 Alcohols, Ethers, Alkyl Ha 27 1490 aa 1433 Jes, and Thiols Clas ala 23 somo «CT oe weoiencon «ons tas aaa os 1.23 Pret, oe 2 1,0. Wea alanced uation forthe compete ‘Wh reference tothe alogeetd organic compos calle CFCs, HCFCS, apd HFCs: (2) Haw do these compounds fein strate? (b) How do these compounds ier i ee intraction With ozone? ‘Give an example of a CFC ac expan why the widospead use of CFCs as ben erie w tbe ‘As we eared in Chapter 13. polymers have very Aileen properties depending in pat) on tei. Iunctonal groups For exampie, poledyiene pve) ‘commonly ed shampoos, where Tom sous selutions in water Polyvinl eerie), onthe other and repels water and swe to make pipes and garden owes. Dace we soul of these ples, and explain wy there i difference, even though bah polymer have several polar bonds. t 4H eneryen 1480 wast sane sae thos rordorteds ig tos) me 1484 Give an eample ofa hlozenated tier commonly sed 24a anette Give two rerons why balogenated thers ae iw wad in place of deter x resale tex fcr out, How des thi et give an Indication of boc labo content? 2.3-Butanedione is commonly used to ge micrnave poor a bery Maver, What dois needed o prepare 2-3butendione by an oxidation reaction? Ay ‘ero 1486ROEM Solo in-chapler an ent ehpter problems hve rit answers provided in Appeni B Chiral Compounds, Chirality Centers, and Enantiomers 1519 Label each ofthe follwing objects as cial or achiral: (a) cals () shoe: () basehall love: () szce ball 1520 Label each ofthe follwing objet 2s chiral shia: (a) Bo: (6) inex ear) seissors; (drinking gas 1521 Explain be fllowing stement Butane (CH,CH,CH,CH, fas a minor image bit it doesnot have an enantiomer, 1522 Explain why the bun body is hia 1523 Draw amior image for each compound, Label each compound ts hiro hia a Ae < een evo . ‘ower ares) (isomers) goo oust (osteny ecg aire 38)1525 1526 1827 Dra mirror image for each compound. Labs! ech compound as chiral o achiral grow a onoH Sono Hoon OH ae et od ey a goct.on bdo ex corsa adeowsua {Label the chirality cone (ion exis) ia each compound (Compounds contin 26 one chy center, sooner © Chips bb omcncucs, dh onronsenen, ‘Label the chia cer (i oe exists) in each ‘compound. Compounds entain zero or one chirality sox onan : enero oy 9 bo proc, «OCHO Label the chili center (i oe exists) in each eyctic ‘compound. Som: compounds contain no chirality centers. oC no 6 © yo 1528 1529 1530 1531 1522 1533 Label he chirality enter i one exists in each etic ‘compound. Some compounds contin no chirality centers, ® O-¢e a 0 Draw the structure of compound tha fis ech escription: ‘an alkane of molecular Formala CH that consis (one chirality center bs an alcool of molecular formula C0 that contains ove chiaiy centr Draw the structure of compound that fis ech description: ‘anal bromide of molecular formula CH,Be that ‘omtans one chirality ccater ‘aio of molecular formula C0, that contains two tirality comers Explain why a carbonyl carbon can never bea chirality Explain why carbon stom thats part of a tuple bond ‘em never be aera center ‘Locate the chirality cener() in each biologically ative ‘compound OP & {essetve comet rem base) eon, o \arespete) croneliebeO) spears ‘rag ram Eau (Gynmete swear1534 1535 1536 [Locate the chiality contents) in each dev, oe ‘coer, “rasan: Demat (races pan rater) “Methamphetamine san ative tml sold ieglly as "speed" meth” oe “erystal meth” Kent the hiraly centr in methamphetamine, and then daw both ‘rantomers in thee dimensions arond the chialiy i ogo, Os rretaronetarine Dotutamin is a hear stimulant used in stress tests measur cardiac fines. Meaty the chirality cemer in ‘obataminc, nd then draw both enantiomers i thre ‘himensons around the eiaity center orn mee Isomers 1537 Howe the compounds inch pure? Arty ‘enicl mole or nao? te oe He =CHs and che We tw be Aecom "wef oa “Goow * wo.c7 oH, Ft oh Sowa og son, 15.38 How are the compounds in each prelate? Are they ‘demical molecules or enantiomers? f en * orn *yer 0:7 o40n confor a Hofman en, én, pe pe Aygo og oon ouwr"ege “og: co 15.39 How are the molecules in eich pa relates? Choose fe Sdemical molecules, constitutional isomer, enantiomer Aiastreomers,o ot komers of eachother. Semmes aes ra ae) CCHLCHLCHR ROH, and CHC =OHLCH.CH, ‘ * @ " atte et dae bn1540 sat sae isa Haw ate the molecules in each prelate? Choose from demicl molecules, costitinal isomers, enantiomen, Aimtercomers, ce mt mers of each other. 1545 on oH a & A concn “Yoo “Hoc? Sonor, B OHOWOKEIOH ard CHLCHOCHONe os conouieio mt ol ono 1546 bcs exer Answer each qestion wth compound of molecular formula Cas 2, Draw dhe structure of «compound that contains (COOH group and one chirality center by Draw the scture ofa carboxylic acd that sa omatutonal omer ofthe compound dawn in pat «, Dra the sirveture of consatonal isomer of the compound dau in par (a), which comin a different functional group. “Answer each question with compound of molecule formule C440. 2. Draw the siracture of «compound that contains an cer group and one chirality comer by Dra the srveture ofan eer hai consti Isomer af the compound daa in part). Draw the stcture of a conatutonal omer of the compound dawn in part (a, which contain a diferent functional group. aw the structure ofthe four constintional isomers of molecule formula CH, that coon aay (CHO) as functional group. Label any chirality enter resent im each compound. Some compounds have no hii enter. Although thre ae four costitional isomers of ‘molecular formula C,H,CI, nly one contains a ciality ‘Seer anc can therefore exist as pai of enantiomers Daw both enaitioner ofthis alkyl chard in thee dimensions around the chy enter, 1887 1540 Fischer Projections ‘Convert each tre- dimensional representation into 8 Freer pectin 0 go a. mee=0H comer os cnrd=on Sr con, beet bron ‘Convert each tice dimension representation into 8 Fister projection. gerne, goon, a onegan cma Noe wedaon oe wo g=o8, Het, ‘Convert each Fischer projection ito a thre dimensional representation with wedges and dashed bonds Hs ‘co0H ante en Oe Cm concn, ona fim ‘Convert each Fischer projection ito a thre dimensional represeiation wath wedges and disted Ponds mcr, oH wha one com en fo, Ons1549. How are the Fischer projection formulas in each pir related o each otber? Are they identical rae they 2 Hw are he compounds in each peated? Ae the ‘compounds enantiomers or diastereomers: [1] A and [2] A and C_ [3] A and Ds [4] Band €: [5] Band (6) Cana De 1 Draw a constinioal isomer of A that contains a ketone, not an achyde ‘Consider the stereoisomers (E-H) drawa below. These ‘compounds are ve-caron sugars, as we wll ar in Chaper 20 GtOH GOH gon LOH Heéon Honda Homdan eo=on t jt i i Hegmoh Hegaon HomgaH Hom gaH yon Gon yon Go e F o 4 2 How are dhe compound in each pir elated? Ae the ‘compounds enantiomers or diastereomers: [1] F and (2 Band Gs [3] Band [and G5] F and Hi [6] Gand Hz ‘Draw a constitutional isomer o Eta contains an aldehyde, not ketone In Chapter 13 we leamed that eis and ans alkenes are erecsemers, Are ci-2-utene and trne2-batene ‘enantiomers or dasersomers? Explain your choice Are ci-2-butene and ran-2-butee cial achiral ‘compounds? Explain your choice. Lactic aids a producto gacose meaboism. During prio of sremsou exercise, atc aidVoresfster han ean be oxidizod resuling inthe aching feling of ted sss eo pn enfin mt we Pi bo coe G0 seme fon we 10 fot, 1850 Hose Fc tn ena i ‘stave? cy ml Sa cor on mee sss weno ton mt vf oves wer Lon a om sos b b coho codon me vo-fon Applications uso "gon soup ton me of out Enantiomers and Diastereomers 1551 Inwhat way ae two enantiomers ferent rom 140 iastercomers? 1552 What are the two major type of stereoisomers? Give an example of each pe 1553 Consider the stereoisomers (A-D) drawn below. Those 1558 ‘compounds ae fourcarton agar, we wil lea Chaps 20, Ho #0 go Ho sebmon Worst ieémoK Homi He Ga0H HE GOH HOM oH HOG Gon Gaon Eon enon crigrconh Late city emer in ae ba sd second Draw both enantiomer of lactic ci in three dimensions around the chili «. Draw Fischer projection Formulas for eh enantiomer of lctic ac [Locate he chirality centers in each vain, 2 (Cage CH LOHEHe 7 tani vondisty