Aldehydes & Ketones Questions and Answers

H 23 0 LiAlH4 NaBH4 P Q Sum of number of alcoholic groups in product P and Q is a 1 b 2 c 3 00 10500 d 5

2 Provide the missing conditions for the following transformations CI X Me CuLi NaBH4 X X Me HO Me These is the answer key to said question but I m just a bit confused how the fir mechanism is carried out I would appreciate seeing how it works Thanks

Phenol 1 NaOH leq 2 D Me 1 x 3 HCN HCI AICI 4 H O r H If Q Number of organic products formed in step 2 significant product R Number of organic products formed in step 3 significant product S Steps in which aromatic electrophilic substitution has taken place Then value of Q R S is

1 Complete the following chemical equations for the following aldehydes ketones undergoing aldol addition followed by condensation For the starred reactions draw the full reaction mechanisms a b NaOH H O NaOH H O NaOH H O NaOH Heat NaOH Heat NaOH Heat

Select the best reagent for the conversion 310 H5C 0 O CH OH OH i PCL5 ii y iii H3O x is LiAlH4 x is NaBH4 y is NaBH4 CH OH y is B H THE H C CH CH CH 2 CH COOH C H OH CH OH OH H C CH CH2 2 CH Hs COOH Cooc s OH

A i 0 CH Cl 78 C ii Zn H O CHJCHO CH3 CO CH3 CO In the above reaction the compound A is 1 CH CH CH CH CH 2 CH C CH CH CH 3 CH3 CH C C CH3 2 4 CH3 CH C CH CH

Identify D in the following reaction sequence SOCL Mg Ether HCHO H 0 CH3CH OH A B C D a n Butyl alcohol b Propanal c d n Propyl alcohol Butanal

hate solution 19 Which of the following reaction is a condensation Para formaldehyde HCHO CH CHO a b e CH3COCH3 d CH CH Polyethylene Paraldehyde Mesityl oxide rea

Allyl chloride A hat is the name of enclosed reaction and B C D Fries rearrangement O H A 250 C X Claisen rearrangement O H CH CH CH O H Claisen rearrangement CH CH CH O H 6 CH CH CH Fries rearrangement P Q CH CH CH

are Enantiomers The relative reactivities of acyl compounds towards 3 nucleophilic substitution are in the order of 1 Acylchloride Ester Acid anhydride Amida fi 1 m

The following compound was made by a mixed Aldol reaction Identify the starting materials other reagents and their order of use Your synthesis should be designed to give this compound as the exclusive product OH O I

Increasing order of equilibrium constants for the formation of a hydrate dddd NH I a IV III II I I II III IV NH II O N III b IV III I II d II III I IV IV OH

An unsaturated hydrocarbon A absorbs two molecules of hydrogen to give a saturated hydrocarbon and absorbs two molecules of bromine to give a tetrabromo derivative Compound A absorbs two molecules of ozone to give a diozonide The diozonide on warming with Zn H O gives a mixture of three compounds acetaldehyde acetone and propan 1 3 dial What is A

36 What reagent and or reaction conditions would you choose to bring about the following conversion 0 a 1 LiAlH4 2 H O c H O NaOH heat CH 0 HOCH2CH OH b H O H SO4 heat d PCC CH Cl 2

Acetaldehyde is treated with excess of methanol in presence of HCI gas The final major product obtained is CH O CH C H OCH3 CH3 CHOCH3 CH3 C OCH3 oc CH3 CH OH OCH3

ere ochemistry major product formed in each step for each of the following reactions Please give an explanation for your answer BzO S a Chx BCI Me NEt CH Cl 78 C b CH3CH CHO 78 to 25 C c H O2 NaOH workup A 82 ds 95 5

One mole of C6H5COCH CH3 is treated with one mole of Br in basic solution the product s formed is are A B C 1 mole of C H5COCB CH3 0 5mole of C H5COCB CH3 1 mol of C H5COCHBr CH Br

1 i H C i CO ii H O H i C6H CH CuLi A H C B H C C H C D H C O Identify D in the following sequence of reaction CH3 CH3 Br CH O B D O CH3 CH3 C CH Ph O Mg Ether CH3 HOS A C Ph CH3 SOCI 2 C C CH Ph A C CH Ph 02 0

Following compounds are separately treated with iodine an NaOH OH ool of 1 iii The compound s which will give yellow precipitate is are i and ii only ii and iii only ii only i ii and iii

An alkene A on reductive ozonolysis gives two aliphatic aldehydes B and C These B and C react with each other in the presence of aqueous K CO3 to give compound R R is on reaction with CH3MgX followed by hydrolysis gives the following compound 37 The compound A cannot be A B D CH I HO CH C CH OH II CH CH

The reaction by which benzaldehyde cannot be prepared is CN CH CN i SnCl HCI ii H O i CrO CH CO O 273 283 K ii H O 1 CH MgBr ii H O CO HCI anhyd AICI CUCI

AbxH CH ct TS more stable Reaction proceed via six membered cyclic transition state ence pericyclic CH CH 03 Oh

The given reaction is called CH3CH COCHZHCH CH CH CH3 Wolff Kishner reduction Stephen reduction Clemmensen reduction hr

CH3 C CH3 O H SO4 C Hg 12 A io Na CO3 Ag powde 8 Product A B Care A Iodoform Acetylene Acetaldehyde B Tri iodomethane Ethyne Acetone C Iodoform Ethene Ethylene glycol form Ethylhydrogen sulphate

A B H i H C Structure of B is Identify correct statement for A and B products a Structure of A is Structure of A is OH ii NH NH OH A iii H O iv LiAlH4 v SOCI Structure of B is a A H i PPh3 ii BuLi iii MeO LOMe H iv H3O

41 What is the major organic product of the following reaction CH CH NHCH CH3 iii a i C H5 C H5 C H5 C H5 b ii ii iv OH N C H5 C H5 N C H5 C H5 c iii v d iv CH CH e v

An organic compound vapour density 37 contains 48 65 Carbon 8 11 Hydrogen and rest Oxygen The compound forms silver mirror on reaction with Tollen s reagent forms yellow precipitate with NaOl and gives positive 2 4 DNP test The compound doesn t contain any chiral atom Which of the following statements is correct The compound doesn t form acrolein on dehydration The compound doesn t undergo aldol condensation The compound doesn t give addition product on reaction with NaHSO3 The compound doesn t evolve hydrogen on reaction with Na metal

Which combination of organic bromides and dicarbonyl compound can be used to prepare the following ketone in a multistep synthesis O CH3CI CH CH CI ii Br

Which compound will give the following compound when mixed with sodium ethoxide in ethanol G eto eto eto eto eto eto me eto etO

cyanohydrine oxime gem diol d hemiacetal 14 Consider a compound RR C OH X Identify X if the compound is cyanohydrin a NH b CN OH d OR 25 What is the product of the reaction of propanal with HCN a CH CH CH N OH b CH CH CHEN NH CH CH CH OH CN CH CH CH N CH a b

15 Which of the following is product of reaction of propanone with excess ethanol a gem diol b acetal chemiacetal d oxime 16 Write the formula of the product of the reaction of 3 3 dimethylpentanal with hydroxylamine a NH CH CH OH C CH CH CHO b CH CH C CH CH C N NH C CH CH C CH CH C N OH d CH CH C CH CH CH OH NH

Which reagents best accomplish the following transformation fer O 1 HOCH CH OH H cat 2 CH3CH MgBr excess 3 H3O O 1 NaOH A 2 CH3CH Br excess 3 H3O O 1 H3O A 2 CH3CH C O CH CH3 O 1 CH3CH MgBr excess 2 PCC HO f

Which of these may not be a product of an aldol condensation 8 O ex

Which combination of reagents would produce the following Robinson product 5 i 1 NaOEt 2 H O A 1 NaOEt 2 H O A 1 NaOEt 2 H O A 1 NaOEt 2 H O A

Why will this synthesis fail HO 1 C H MgBr ether 2 H O HO HO The reactant organic compound has a group that will adversely react with Grignard reagent O The product formed will be too unstable because of two hydroxy groups with strong dipole effect O Because of the highly polar hydroxy group in the reactant organic compound it will not dissolve in ether solver O The nucleophilic attack by the Grignard reagent is sterically hindered by the ring structure

Why will this synthesis fail S HO 1 C H MgBr ether 2 H O HO HO O The reactant organic compound has a group that will adversely react with Grignard reagent O The product formed will be too unstable because of two hydroxy groups with strong dipole effect O Because of the highly polar hydroxy group in the reactant organic compound it will not dissolve in ether sol O The nucleophilic attack by the Grignard reagent is sterically hindered by the ring structure

Determine the principal product of the following reaction ei O O O 1 LDA THF 15 C 2 CH3 CHCH Br The zi

Which structure is consistent with this mass spectrum O Rel Intensity 100 80 60 O OH 40 20 OH CHO 0 0 20 40 55 m z 60 80 98 100

What is the organic product of this reaction CH OH H H CRO4 excess

Draw the mechanism for the witting reaction cinnamaldehyde with BTPC to form the 1 4 diphenyl 1 3 butadiene Draw the mechanism for this reaction and upload it here

O O What is the product of the following reaction HO Ea 0 O O EtONa EtOH i OH OH H O0 A

Here is the product obtained from Robinson Annulation What would be a suitable reagent that would react with ethylacetoacetate AAE to give this compound COOH are of os s

What is the most likely product if the following compound is treated with ethanolic sodium ethoxide que l af od go

Question 30 2 Choose the correct base to produce this regiochemistry 1 Base 2 CH31 OLDA BuOH NaOMe

What are the strongest intermolecular forces in CH3OH Oion dipole forces hydrogen bonds O covalent bonds O dipole dip le forces London forces

Direct alkylation OH LDA THF EtBr

0 az 4 U 8 L or a Az A B a 2 A az B bi A B A bi13

From the choices provided below list the reagent s in order that will yield the transformation shown above List your answer as a series of letters in the order the reagents are used with no commas separating them No more than four steps are required for this synthesis Use the minimum number of steps possible Reagents may be used more than once in subsequent steps Ex dop corresponds to 1 NaCN 2 NaOH 3 PCC NOTE The order in which you list your letters matters 8 a HIO4 b HS Na H O c CH3O Na CH OH 9 H O d NaCN h H Pd e CH3CH S Na i i k f Br2 CCl4 e 1 H SO4 H O HBr heat RCO3H NH3 m NBS hv n OsO4 H 02 0 NaOH P PCC Previous

1 Select two pairs of dissimilar pairs of aldehydes give aldol products four possible of the reaction between these self as well as cross Also give conjugated enone in each case

Complete the assignment as discussed in the class 1 Select two pairs of dissimilar pairs of aldehydes give aldol products four possible of the reaction between these self as well as cross Also give conjugated enone in each case 2 Select three pairs of dissimilar pairs of ketones give aldol products eight possible of the reaction between these self as well as cross Also give conjugated enone in each case