Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 20, Problem 20.58P
What Grignard reagent and
a. 
b. 
c.
e. 
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10. Complete the substitution reaction of 2 pentanol with these reagents.
Reagents & Reaction Conditions use practice sheet. Please write only
major products, minor product like water, other gases are not
required.
Hint: In substitution of alcohol, we generally substitute OH group
with Halogens like cl, Br, F using some reagent containing
halogens. Ensure to add halogens to the same carbon number
where you are removing OH from
Examples
Alcohols can be converted to Alkyl Halides with HX acids
HBr
H₂O
HCI
+ H₂O
HI
+
H₂O
CH,CH₂OH + SOCI₂
CH,CH₂OH + PCI₁₂
A
BBYJU'S
CH CHCI + SO₂+ HCI
CH₂CH CIP(OH), + HCI
CH,CH₂OH + PCI CHCHCI + POCI + HCI
CH,CH₂OH + PBr, CH,CH,Br + P(OH), + HBr
1. Reaction with HBr with 2 Pentanol
2.Reaction with HI with 2 pentanol
© Byjus.com
3.Reaction with HCI+ZnCl,, with 2 pentanol (Zncl2 is catalyst no role)
4.Reaction with SOCI,, with 2 Pentanol
5.Reaction with PBr; or PCl, with 2 pentanol
3. Is 2-methyl-2-propanol a primary, secondary, or tertiary alcohol? Write
out the
structures of 2-methyl-2-propanol and also any oxidation products of 2-
methyl-2-
propanol. If there is more than one oxidation product, give the structure of
each
of the products.
4. 2-Propanol is the IUPAC systematic name of this alcohol. It has a
common name
by which it is much better known (You'll see it in the grocery store or
pharmacy).
Give that common name
5. Aldehydes can be synthesized by the oxidation of. Please choose from
below choices
A. Primary alcohols
B. Secondary alcohols
C. Organic acids
D. Inorganic acids
6. Tertiary alcohol Can undergo oxidation. yes or no. ? If yes then answer the
product.
Finish the reactions
hand written please
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 20 - Prob. 20.6PCh. 20 - Problem 20.7 Draw the products formed when is...Ch. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Draw the structure of both an acid chloride and an...Ch. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - What product is formed when...Ch. 20 - Prob. 20.16PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Draw the product formed when each organometallic...Ch. 20 - Draw the product of each reaction. a.c. b.d.Ch. 20 - Draw the products including stereochemistry of the...Ch. 20 - What Grignard reagent and carbonyl compound are...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organocuprate reagent is needed to convert...Ch. 20 - What reagent is needed to convert (CH3)2CHCH2CHO...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - Prob. 20.39PCh. 20 - Draw the product formed when CH3CH2CH2MgBr is...Ch. 20 - Draw the product formed when (CH3CH2CH2CH2)2CuLi...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.43PCh. 20 - What reagent is needed to convert...Ch. 20 - What reagent is needed to convert...Ch. 20 - Draw the products or each reduction reaction. a....Ch. 20 - Prob. 20.47PCh. 20 - Draw all stereoisomers formed in each reaction. a....Ch. 20 - Prob. 20.49PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.52PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.54PCh. 20 - Draw a stepwise mechanism for each reaction. a. b.Ch. 20 - Prob. 20.56PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - What Grignard reagent and aldehyde or ketone are...Ch. 20 - Prob. 20.59PCh. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organolithium reagent and carbonyl compound...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.63PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - Synthesize each compound from cyclohexanol using...Ch. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Devise three different methods to prepare each...Ch. 20 - Convert benzene into each compound. You may also...Ch. 20 - Design a synthesis of each compound from alcohols...Ch. 20 - Synthesize each compound from the given starting...Ch. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.84P
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- Part A Identify each alcohol as primary, secondary, or tertiary Drag the appropriate items to their respective bins. CH₂ H₂C- -C-OH HO CH₂ Primary Он OH CH₂ OH CCH₂OH CH₂ сн Secondary Tertiary Reset Help CH,CH₂ (CH)CHCH,OH CH,CH,CH,CCH, CHOH CH₂ Different types of alcohol groups Alcohol and its reaction: 8. Combing two alcohol molecules below and completing the reaction with Product .( Hint Reaction called etherification as ether is formed and name the ether once you complete the reaction. Hint.: R-O-H+H-O-RR-O-R Do the reaction: CH₂OH + CH₂OH---→ + H-O-H 9. Write the reaction of formation of alcohol from alkene by adding water: Addition reaction also called hydration reaction as we are adding water which occur always in presence of acid Hint: Break the double bond and add H and OH if symmetrical then add anywhere if unsymmetrical then follow Markovnikov rule H should go to that double bone carbon which has more hydrogen CH2=CH2 + H₂O-→arrow_forwardComplete the reaction hand written pleasearrow_forwardPredict the major products of this organic reaction: HBr (1 equiv) cold ? Some important notes: • Draw the major product, or products, of this reaction in the drawing area below. • You can draw the products in any arrangement you like. • Pay careful attention to the reaction conditions, and only include the major products. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. • Note that there is only 1 equivalent of HBr reactant, so you need not consider the case of multiple additions. dm Re Explanation Check ©2025 McGraw Hill LLC. All Rights Reserved. Termarrow_forward
- b) Use curved arrows to show the reaction of the radical with hydrogen bromide. Br: Br H .. Answer Bankarrow_forwardIndicate the reaction products when CH3COCH2COOCH2COOC2H5 (ethyl acetoacetoacetate) reacts with 1º OH-/H2O and 2º H3O+arrow_forwardDraw the formula of the compound 4-cyclohexyl butanamide?arrow_forward
- What is the formula of the compound 3-isopropylcyclopentane-1-carbonyl chloride?arrow_forwardIndicate the products of the reaction between CH3COCH2COONa (Sodium acetoacetate) and BrCH2COOC2H5arrow_forwardIndicate whether the product of the reaction between Naphthalene and CrO3 in acetic acid at 25ºC is 1,4 naphthoquinone or phthalic anhydride.arrow_forward
- Indicate the products of the reaction between CH3COCH2COOC2H5 and Na+-OC2H5.arrow_forwardPrimary, Secondary, and Tertiary Alcohols O-H O-H O-H R₁-C-H R₁-C-H R₁-C-R₁ H R₂ R₂ Primary Alcohol Secondary Alcohol ChemistryLearner.com R stands for Carbon group like ethyl methyl propyl Tertiary Alcohol If 1 carbon group with two H attached to alcoholic carbon, then primary If 2 carbon group and 1 H are attached to alcoholic carbon, then secondary IF 3 carbon group and no H attach to alcoholic carbon then tertiary. The bottom line Starting "Weak" oxidant material PCC, DMP, Swern, etc Primary alcohol Aldehyde OH Secondary alcohol Ketone OH "Strong" oxidant KMnO4, H₂CrO4 (or equivalent) OH Carboxylic acid 요 Ketone No reaction No reaction Tertiary alcohol 1. Is ethanol a primary, secondary, or tertiary alcohol? Write out the structures of ethanol and any oxidation products of ethanol. If there is more than one oxidation product, give the structure of each of the products. 2. Is 2-propanol a primary, secondary, or tertiary alcohol? Write out the structures of 2-propanol and any…arrow_forwardFormulate the reaction: Naphthalene with CrO3 in acetic acid at 25ºCarrow_forward
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