Chem+118C+SSI+2010+Midterm+2+key

Chem+118C+SSI+2010+Midterm+2+key - Chem 118 C Summer...

Info iconThis preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chem 118 C Summer Session I / 2010 Second Midterm July 20, 2010 Instructor : Nambiar This exam contains seven pages and seven problems. Please make sure that your copy contains all the seven pages. If there is a problem, please let us know before you start answering. Please answer all questions. Name: __________________________________ Last First MI pected organic product (5) formed in the d otherwise, you can assume that all "No Reaction". 1. (30 pts). Draw the structure of the ex following reactions. Unless mentione reagents are present in excess. If no reaction occurs, write m 1. CH3] 1) -CH3 \’—/ 2. AggO/HZO/A CH3Li _ 2) (C2H5)2NH C gm 3) QHOH LiA1H4 CH20H a 1. LiOR 4) CH3CH(COOR)2 ' 2. CH2=CH—CO-CH3 KMnO4/ KOH / A 5) /fl\/C(CH3)3 Lg‘lZCHZ; CH(CH3) 2 1. Br2/ hv 0 2.NaOCH3/A H3 (CH3CO)2O(1eq)/A «1 A 7) (CH3)2N~@OH (L/w—{E‘Ufireflg 7 j '9‘ in” i J 1. Li OH 8 CH 0 H V .. a» ) 3—00 M» 019 , _ ( J 2.C02 0H 3.CH3OH/H+/A “WGME / C 9) CH3CH:CH-O-CH2CH=CH2 / 10) \< 1. n—BuLi x7 w r; I M A/ _, u N V4;{:'""Iv A,‘ g R 2.C6H5CHO A & 3. HgClz / H20 / A &' ff 11 (20 pts) Show detailed reaction mechanisms for the following, showing the structure of the expected product. QHQH H104 / H20 (Excess) + a) ' .h‘ n (E W“ W a“ ‘fixil - R cave K “0” XV 2' ' ;?b \. ‘6 C) \ vr J R v F) L I} g 3 [Sr ’ v V} 0 LL R 64.}: A g/wa If r a“; MOE; / " O“ k 0 u m w C6H5CHO . fl " _ [/8 WW ” \ . in. q 1“. ! ‘l l {O <\ v 414. a, H [K , * V/ \ (<31 7 2/ '7 \ N : IQL 1/8'\ ‘ \f/E/Cq'\ ‘33 ‘d 8 \ ’L b M' 7 0 5 u H [6) w 6’ C H 1/ s 0 ‘ k4 «1‘1" TK‘IL L? H 4 ,~ ‘i’ , ‘L\--r r/"\ L: ( ‘ ,3 ./ ' ""”"’” z/ > s K ‘ (5/7 w! Ill. (24 pts). Show how you would carry out the following transformations showing the reagents you would use in each step and the structure of the intermediate products formed. 1. HOCO(CH2)5COOH , C}-OCH3 [M 1, (algal/Ml ’ +63 :- 4 9‘ «may , C F66 {figs (/9 J C" A VM‘ . ‘7 'V 1 A \j F" q H /1‘ l ; “A - ’ Va v ‘ Edwwfkp' '/ W Vii/J! OCH3 . 2 @ .___._.- ,.—CH2Cl-12CH? / /; r47 \j H g {fiafiwr $- i 7 ' t4 {QM/fl; 9‘75? (97 e? --~ 197 Ma 4%; a 2 _n x W" 2% M (W LA; f $177041? ilgwfl W k a 6L6 / / ( M“ //\\/UI 3 CH(CH3) 2 HzoCHS ——-————> C07 I /r 5 _’ At 1 1* (:1 4:: V K a C} -- Milly L/ following proton NMR spectrum. IR 1. Deduce the structure of compound A. nd A is: a) heated with 6M aqueous 3 v1. (15 pts).C0mpound A (C3H15N03) gave the spectrum showed strong absorptions at 1695 cm“ What is the product you expect to get when compou NaOI—I; b) reacted with LiA1H4 \CC 3K 2/64!“ ( 3‘2. 3 “5 V231“ '(CH3)45i . {at d» ,. LiA1H4 w A c 3 tang ~ N -~~64§~% ~ G g f ,_ C4: 6 &/%‘ (“fl Li 0 IV. (15 pts) Provide a systematic name or draw the structure as appropriate for the following compounds. 1. C2H5CO NH-CH(CH3)2 ’ in’CUWU‘béf ,5 , a l/ (524’ 2. CH3CH20CH2COOC2H5 ' i , "‘ ' V ,1; l (C i, F” 3, @CHg—CHg—N(CH3)2 {VI M‘nDECflW 3’] 4. p-Nitrophenyl2-bromobutanoate ' \J %/ \D 2 5.CH30 CH2CH2—@~—CONH2 Oz, ~ V. (6pts) Rank the following compounds in decreasing order of basicity. H OH OH NH2 NH2 H 5% C7 i] Q7 N 02 02 A B C D L F F») I; E Trig} 69 [> C High Basicity Scale Low U‘! V11. (10 pts) ‘ ' ‘ I H HO o 033 H H - to OH HO . ’0 . _ OH Circle the compounds that do not show reducing properties. H (3h0H_ HO OH OH // \__ /”/ f” 7" \\,_ / ‘ CHCH3 a :\ H } CHO / ' egg. 3; CHCH; f/ Q HO OH 2 / ’///’/ U W4 \—'/, ...
View Full Document

This note was uploaded on 04/05/2012 for the course CHE 118 taught by Professor Shaw during the Fall '10 term at UC Davis.

Page1 / 7

Chem+118C+SSI+2010+Midterm+2+key - Chem 118 C Summer...

This preview shows document pages 1 - 7. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online