Name: Date: Period: Organic Chemistry Packet

Transcription

1 Organic hemistry Packet Basic Organic hemistry Organic chemistry centers n the chemistry f a few elements, mainly, and a few thers: Fr the mst part (and at all times in this class), all atms bey the Octet Rule. This means: arbn frms bnds and has lne pairs. Nitrgen (and its family) frms bnds and has lne pair. Oxygen (and its family) frms bnds and has lne pairs. The halgens frm bnd and have lne pairs. ydrgen frms bnd. What elements will we cmpletely ignre fr the next few weeks? Prperties f Organic mpunds: - d nt disslve in water melting pints. Why? Increases as increases. Why? React than inic cmpunds. Why? Types f mpunds: - all carbn atms are attached by bnds - at least ne r bnd is present Line-Bnd Structures These are exactly like Lewis Dt Structures (except yu leave ut the lne pairs, fr simplicity) Draw the Line-Bnd Structure fr 32(3)23 in the space belw: Wh wants t d that again??? (Me either )

2 Skeletal Structures These structures are much cleaner, but at first it seems like many things are missing. wever, as with mst chemistry, there are rules that help with this! What d yu ntice abut these tw structures? Rules fr Drawing Structures: arbns are represented by the f a line r the f tw lines w many carbns are in each f the fllwing structures? Number them. ydrgens that are attached t are drawn. w many hydrgens are in each f the fllwing structures? Draw them in! All atms carbn and hydrgen must be shwn. ydrgens attached t these atms must als be shwn.

3 Practice: Draw the skeletal structure fr the fllwing mlecules: Write the frmula fr the fllwing mlecules. Draw the line-bnd structure fr the left clumn. Br l O O O O

4 mewrk 1 Directins: Draw the skeletal structures fr the fllwing mlecules. 1) 323 5) 3222OO 2) 3(3)(3)223 6) Br(3)OO 3) 322(23)23 7) 322OO23 4) 2O 8) 322O23

5 Organic Nmenclature (IUPA Internatinal Unin f Pure & Applied hemistry) ydrcarbns cmpunds that are made f nly and Base Names: Prefix Meth Eth Prp But Pent ex ept Oct Nn Dec Length f arbn hain Alkanes simplest hydrcarbns Saturated (nly bnds) General frmula: What is the frmula fr an alkane with 5 carbns? What is the frmula fr an alkane with 20 carbns? Name the fllwing alkanes: Alkenes unsaturated hydrcarbns with ne bnd General frmula: What is the frmula fr an alkene with 8 carbns? What is the frmula fr an alkene with 43 carbns? Name the fllwing alkenes: Ismers mlecules with the same mlecular frmula but different structural frmulas 1-pentene has the duble bnd between the 1 st and 2 nd carbn 2-pentene has the duble bnd between the 2 nd and 3 rd carbn Add all f the pssible names t the alkenes listed abve!

6 Alkynes unsaturated hydrcarbns with ne bnd General frmula: What is the frmula fr an alkyne with 7 carbns? What is the frmula fr an alkyne with 34 carbns? Name the fllwing alkynes (all pssible ismers): Alkyl Grups branches that have ne less hydrgen than the crrespnding alkane isprpyl sec-butyl tert-butyl isbutyl Write the frmula AND draw the skeletn structures fr the fllwing alkyl grups: Prpyl Butyl Decyl yclalkanes hydrcarbns with a ring structure General frmula: Write the frmula and draw the skeletn structure fr the fllwing cyclalkanes: yclprpane (very uncmmn) yclbutane yclpentane

7 mewrk 2 Directins: Write the frmula and draw the skeletal structures fr the fllwing hydrcarbns. 1) yclheptane 4) Prpene 2) 3-ctene 5) 2-hexyne 3) 1-decyne 6) 3-cten-1-yne Directins: Name the fllwing hydrcarbns using the IUPA Rules. 1) 5) 2) 6) 3) 7) 4) 8)

8 Branched ydrcarbn Nmenclature Find the lngest cntinuus chain f carbns. Nte: This may nt be straight! This is yur chain. Number the carbns in yur parent chain s the branches are attached t the numbered carbns. Add t the names f the grups t identify the carbn they are attached t. These numbers becme t the parent chain. Use prefixes t indicate any branches that appear mre than nce. Di Tri Tetra Penta List the alkyl grups in rder. Use punctuatin: t separate numbers frm each ther t separate numbers with wrds If a duble r triple bnd is present, start numbering clsest t the duble/triple bnd! Practice: Number and name the fllwing branched hydrcarbns:

9 Draw the skeletn structure fr the fllwing branched hydrcarbns: 3-ethyl hexane 2,2,4-trimethylpentane 2,3-dimethylhexane 5-ethyl trimethyldecane Methylcyclpentane 5-ethyl-2-ctene

10 mewrk 3 Directins: Draw the fllwing skeletal structures. 1) 4-ethylctane 4) 3-ethylpentane 2) 2-methylnnane 5) 3-ethyl-2-methylheptane 3) 3,3-dimethylpentane 6) 3-ethyl-4-(1-methylprpyl)-2,2- dimethylctane Directins: Name the fllwing branched hydrcarbns using IUPA Rules. 1) 5) 2) 6) 3) 4) 7)

11 Alkyl alides mpunds that are frmed when any replaces ne r mre hydrgens in a hydrcarbn. Use a t specify where the halgen is attached. Practice: Name the fllwing alkyl halides: Draw the skeletn structure fr the fllwing alkyl halides: Brmcyclhexane 3-chlr-1-pentene 1-brm-7-id-heptane Alchls mpunds that are frmed when a grup (-O) replaces ne r mre hydrgens in a hydrcarbn. Primary alchl the O grup is attached t an carbn Secndary alchl the O grup is attached t a carbn Tertiary alchl the O grup is attached t a carbn

12 T name alchls, replace the final e with l. Methane Ethane Prpane Butane Pentane Use a number t specify n which carbn the O grup is attached (shuld be n the lwest pssible) Draw and name all pssible structural ismers f pentanl. Why are there nly 3? Practice: Name the fllwing alchls: Draw the skeletn structure fr the fllwing alchls and classify them as primary, secndary, r tertiary: 2,2-prpanedil 3-ethyl-3-hexanl 4-methyl-cyclhexanl tert-butanl 3-methyl-1,10-decanedil 4-penten-2-l

13 mewrk 4 Directins: Draw the skeletal structures fr the fllwing mlecules. 1) Ethanl 4) Isbutanl 2) 2-chlrprpane 5) 3-chlr-cyclpentanl 3) Flurmethane 6) 2-brm-3-methyl-1-butanl Directins: Name the fllwing alkyl halides and alchls using the IUPA Rules. 1) 4) 2) 5) 3)

14 arbxylic Acids mpunds that are frmed when a terminal atm is replaced by a carbxyl grup (-OO) T name carbxylic acids, replace the final e with ic acid Methane Ethane Prpane Butane Pentane Why des a carbxylic acid functinal grup have t be n the END f a hydrcarbn chain? Aldehydes mpunds that are frmed when a terminal atm is replaced by a O grup. T name aldehydes, replace the final e with al. Methane Ethane Prpane Butane Pentane Why des an aldehyde have t be n the END f a hydrcarbn chain?

15 mewrk 5 Directins: Draw the skeletal structures fr the fllwing mlecules. 1) exanic acid 4) 2-methylbutanic acid 2) Ethanal 5) 2-cyclhexyldecanal 3) 5-flurpentanal 6) 2,3,4-triethylnnanic acid Directins: Name the fllwing carbxylic acids and aldehydes using the IUPA Rules. 1) 4) 2) 5) 6) 3)

16 Ketnes mpunds that are frmed when a =O grup is in the middle f a hydrcarbn chain. T name ketnes, replace the final e with ne. Add a number t dente the carbn in the =O grup Prpane Butane Pentane exane Why are methanne and ethanne nt pssible cmpunds? Ethers mpunds that are frmed when an xygen atm is bnded t tw hydrcarbn chains. T name ethers, name the tw hydrcarbn chains as alkyl grups and then add ether. List the shrter carbn branch first.

17 mewrk 6 Directins: Draw the skeletal structures fr the fllwing mlecules. 1) Isprpyl cyclhexyl ether 4) 3-decanne 2) 1-flur-3-hexanne 5) 2,2-dimethyl-4-heptanne 3) Ethyl 2-methylpentyl ether 6) Diisprpyl ether Directins: Name the fllwing ketnes and ethers using the IUPA Rules. 1) 4) 2) 5) 6) 3)

18 Esters mpunds cntaining a OO grup in the middle f a hydrcarbn chain. T name esters, name the alkyl chain AFTER the OO grup, then name the carbn chain including the =O carbn, replacing the final e with ate. Amines mpunds that are frmed when a hydrgen atm is replaced by a nitrgen grup (-N2) T name amines, replace the final e with amine Methane Ethane Prpane Amides mpunds cntaining a ON2 grup at the end f a hydrcarbn chain. T name amides, replace the final e with amide Methane Ethane Prpane

19 mewrk 7 Directins: Draw the skeletal structures fr the fllwing mlecules. 1) Isprpanamine 4) 2-methylbutanamide 2) Ethyl pentanate 5) Isprpyl ethanate 3) yclpentanamine 6) 4-chlrpentanamide Directins: Name the fllwing esters, amines and amides using the IUPA Rules. 1) 4) 2) 5) 3) 6)

20 Summary Sheet Make yurself a summary f all the functinal grups n the back f this page! This will be a quick reference sheet fr yur final exam.